People have long been fascinated by their fellow humans’ daily routines — particularly the routines of the famous and successful.

We feel there are likely habits common to high-achievers, which, if duplicated, would help us all elevate our own work. This is especially true of the choice of when to wake up each day. There seems to be special weight placed on this decision, a feeling perhaps born of the idea that how you start something determines how the rest of it will go. The time you get up each day seems to be a potentially impactful pivot point from which the quantity and quality of one’s ensuing work and decision-making will flow.

It’s popularly thought that the best time to wake up is early in the morning. “The early bird gets the worm”; “Early to bed, and early to rise, makes a man healthy, wealthy, and wise.” Beyond even the idea that rising early has a practical benefit in aiding productivity, there’s a moral connotation to this habit as well; early risers are perceived as having more discipline, while their late-rising peers are often perceived as lazy.

Is there truly a correlation between waking up early and success?

The Morning Person as Success Story: Considering the Evidence

I decided to find out by re-reading Mason Currey’s Daily Rituals: How Great Minds Make Time, Find Inspiration, and Get to Work. The book is a collection of short descriptions of the daily routines of 161 eminent authors, mathematicians, architects, and artists — folks who did creative work and were able to set their own schedules. As I read each entry, I kept a tally of when each individual woke up. I only marked down those for whom a specific time was given, skipping entries where the time was kept more vague (e.g., “early morning” or “early afternoon”). In the few cases where a person woke up not at a straight o’clock (i.e., _:00) and instead arose at _:30, or were said to arise sometime between __ and __, I “rounded” to the earlier hour in half the cases, and to the later hour in the other half. My aim was just to get a feel for the general range of times that these folks got up each day.

This gave me the wake-up times for a sample set of 68 individuals, and these have been graphed below:

It’s worth noting that almost all those who woke up at 4 am took a long nap either several hours after rising or in the afternoon.

As you can see, there were indeed many early risers among this high-performing group, with the most common wake-up time being 6 a.m. Yet it is just as significant to observe that there were as many folks who woke up at 8 a.m. as 5 a.m., and almost as many who woke up from 7 a.m. on, as at 6 o’clock or earlier. And those in the former category were no less creative/productive/successful than the latter. Having a good morning to set the tone of your day, it seems, can happen at almost any time.

The real takeaway, then, is that there isn’t in fact one “right” time to wake up if you want to be creative and successful. The answer to the question of “What time should you wake up to do your best work?” is: “Whatever time works best for you.”

The novelist Bernard Malamud came to this same conclusion:

There’s no one way—there’s too much drivel about this subject [of copying other people’s routines]. You’re who you are, not Fitzgerald or Thomas Wolfe. You write by sitting down and writing. There’s no particular time or place—you suit yourself, your nature. How one works, assuming he’s disciplined, doesn’t matter. If he or she is not disciplined, no sympathetic magic trick will help. . . . Eventually everyone learns his or her own best way. The real mystery to crack is you.

Experiment. Be self-reliant. Find your own optimal routine. It’s worth noting that not everyone Mason profiled began working right after waking up; they might arise in the morning but first attend to other important tasks and activities before beginning work in the afternoon or evening. They might get in a morning workout or spend the first few hours of the day with loved ones. There are multiple components in one’s schedule to play with.

Now, all this being said, there was one commonality between all the profiles that was so nearly universal that it should be given real credence: despite the many varied ways in which each individual arranged their daily routine, almost all of them had a routine, and stuck to it religiously.

The Importance of a Regular, Consistent Daily Routine

“My experience has been that most really serious creative people I know have very, very routine and not particularly glamorous work habits,” explained the modern composer John Adams.

“Routine is a condition of survival,” asserted the writer Flannery O’Connor.

The novelist John Updike felt that having a daily routine was so important because it “saves you from giving up.”

These sentiments were shared even among those whose overall personalities and lifestyles were fairly hedonistic; for example, though the modern artist Francis Bacon and the writer Ernest Hemingway could be called night owls and sometimes stayed up late partying (the former drank six bottles of wine a day), they would nonetheless still wake up early and get to work, hangovers and getting enough hours of sleep be damned. A productive morning and day were always on the docket. As Papa put it, “You have to work every day. No matter what has happened the day or night before, get up and bite the nail.”

Further, among the individuals Currey profiled, such revelry was far more the exception than the rule. Despite the reputation of creative types as living freewheeling, iconoclastic lives, the vast majority kept to routines — both within and outside their work schedules — that were surprisingly quiet, prosaic, and closed-in. “I love the cell,” Voltaire exclaimed, and so did many of his productive peers throughout time.

The morning habits and daily rituals of famous authors and artists typically look something like this: wake up, drink a glass of water, eat breakfast, do a few hours of work, eat lunch, do a few more hours of work, eat dinner with spouse, take a walk (if one stand-out commonality did emerge from surveying all these routines, it’s taking a daily walk, or two; almost a third of the individuals profiled kept this habit), watch television or read a book, go to bed. Entire days would pass like this. They went out surprisingly seldom, and this was not an incidental choice but an intentional one; limiting distractions expanded their creativity.

Or as Gustave Flaubert put it, “Be regular and orderly in your life like a bourgeois so that you may be violent and original in your work.”

With our archives 4,000 articles deep, we’ve decided to republish a classic piece each Sunday to help our newer readers discover some of the best, evergreen gems from the past. This article was originally published in March 2021.

This article was originally published on The Art of Manliness.

When you have a high-responsibility job, your work hours can readily bleed beyond the 9-to-5. You’ve got a lot of tasks that seem urgent and important and an endless number of people who need responding to. This is of course especially true in the age of smartphones and digital communication, when bosses and colleagues feel free to message you at any time — even when you’re nominally “off the clock.”

The problem of ever-expanding work hours may be more prevalent these days, but it’s not new.

General George Marshall faced the issue almost a century ago. And found a way to overcome it.

As Chief of Staff of the United States Army during World War II, Marshall oversaw the expansion of a military ranked seventeenth in the world into the most powerful fighting force in human history. He managed nine theaters of war, helped oversee the Manhattan Project, and directed millions of personnel across the globe. His job was arguably the most complex administrative role of the twentieth century.

Day and night, there was always some issue, in some branch, in some part of the world that Marshall could be tending to, and that he could have convinced himself was urgent — the fate of democracy hung in the balance, after all!

But Marshall walked out of the War Department at 5:00 PM almost every single day and didn’t think about work until he showed up to the office the next morning.

How did a guy who oversaw the largest, most complex military campaign in human history do that?

The Marshall Plan — For Taming His Work Schedule

Here’s how General George Marshall kept the tentacles of his work responsibilities from expanding into an all-encompassing chokehold:

Marshall Gutted the Bureaucracy

When Marshall took over as Chief of Staff in 1939, the War Department was a mess. Over sixty different bureaus and agencies had direct access to his office, which meant he spent most of his time refereeing petty jurisdictional squabbles instead of planning a war. Marshall described himself as being “worked to tatters on minor details.”

So in early 1942, he blew the whole thing up. He directed Brigadier General Joseph McNarney to streamline the organization. The results were dramatic. The number of people with direct access to Marshall dropped from over sixty to roughly six. He created semi-autonomous commands — Army Ground Forces, Army Air Forces, Services of Supply — that handled their own training and supplies procurement.

And he established the Operations Division (OPD), which functioned as a single command post that filtered the entire war’s worth of data into a manageable stream of intelligence and proposed actions.

The OPD was the key to the whole thing. Theater commanders had to send copies of all combat-related messages to the OPD, and the OPD’s job was to synthesize that information and only bring the “broad phases of plans or changes” to Marshall. When Marshall sat down at his desk each morning, the information had already been distilled by competent people. His only job was to exercise judgment.

Marshall Demanded the One-Page Memo

Marshall had a rule: if you couldn’t explain your problem and propose a solution on a single page, you didn’t understand the problem yet. The one-page memo requirement forced his staff to do the hard thinking before they walked into his office, which meant Marshall could review dozens of critical strategic questions in the time it took other commanders to get through a single briefing.

Marshall Maintained Strict Boundaries

Marshall’s daily routine was boringly rigid, which is what made it effective.

He woke up at 6:30 AM and was at the War Department by 7:30. He’d get a global briefing at 8:00, and then he’d dive straight into strategic work through the morning.

He ate lunch and followed that up with a power nap. Marshall was a big advocate of the midday nap and pushed Eisenhower and MacArthur to adopt the habit.

After his nap, he worked through the afternoon until 5:00 PM.

At 5 PM on the dot, he’d leave the office for the day.

What did he do in his personal time?

Horseback riding. It was a non-negotiable part of his day. Marshall rode with his stepdaughter, Molly, or alone with his dog, Fleet. He specifically refused to ride with colleagues because he didn’t want “office talk” creeping into his recovery time.

After riding, he had dinner with his wife, Katherine, and was in bed by 9:00 PM.

Marshall understood that if you work yourself to exhaustion, you won’t have the mental clarity and energy to actually do the work you’re supposed to do. He was able to get more done during the time he did work because he was well-rested (thanks to the power nap and strict sleeping schedule) and refreshed (thanks to horseback riding and strict leave-the-work-at-work policy). And by standardizing his schedule, he eliminated that low-grade decision fatigue that makes you stare at your inbox for 10 minutes without actually writing any emails or causes you to snap at your kid for asking a simple question.

Even on the morning of December 7, 1941, Marshall was out on his horse, Prepare, at Fort Myer. Some people at the time criticized the optics. Why wasn’t the Army Chief of Staff at the office as soon as that Day of Infamy occurred? But Marshall understood there was nothing he could do immediately, so he took the time to get his mind right before he had to get down to business. His ability to remain “especially cheerful and optimistic” in the hours and days after Pearl Harbor was a direct product of those physical and emotional reserves he built up through deliberate rest and relaxation.

So, What Can We Steal From Marshall?

While we may not have to manage nine theaters of war, nor have Marshall’s latitude in restructuring administrative operations, I think we can use some of Marshall’s principles to tame our own workload into a more humane schedule. It’s all about working effectively when you’re “on the clock,” and actually checking out when you’re off it.

Cut the number of communications you have coming in. How many people have direct access to your time and attention? How many pings and dings do you receive?

Marshall cut his direct reports from sixty to six. You may not be able to be that aggressive, but you can identify the nonsense that eats your day without producing anything useful. Aggressively reduce the number of apps you have to check for communication. Use filters in your email so that only the important stuff shows up there. Turn off notifications from web services that you use. Use your phone’s Do Not Disturb feature and only allow VIPs to call or text you. Don’t attend meetings where you’re not needed. Get rid of the deadwood.

Organize your communications and answer them in blocks. You don’t have an OPD to synthesize your info and give you a one-page memo about it. But you can turn the intelligence you receive into a manageable stream and claw back a lot of time and bandwidth by keeping information and conversations organized into set channels.

In my conversation with business efficiency expert Nick Sonnenberg, he said that 20% of an employee’s time can be spent just looking for where information about a certain topic/project ended up. To shrink these “scavenger hunts,” he recommends designating certain channels for certain communications: text for personal matters, email for external communications with clients, vendors, and partners, and apps like Slack for internal team messages. By eliminating the search for where particular information resides, Nick’s found that workers gain back hours of time.

I also recommend establishing a “correspondence hour” — set blocks of time when you answer messages. In the morning, I glance through my emails, texts, and messaging apps and take action on anything that needs action. At night, I do the same thing. Doing this in set, consolidated blocks saves time over constantly ping-ponging back and forth through apps throughout the day.

Pick your 5:00 PM. You don’t need to literally knock off every day at 5:00 PM like Marshall did, but you need to establish a hard boundary where you take off your general’s cap and put on your personal one.

Marshall rode every evening because, without those hours on the horse, he knew he’d eventually start making bad calls with millions of lives on the line. Find your horseback riding. It could be working out, building model trains, or reading a book. Whatever. Pick something that has nothing to do with your job and do it as a way to transition from work mode to private mode.

If you’re an employee rather than a boss, it may be harder to say no to responding to messages when you should be off the clock. But try to have that boundary-setting conversation with your supervisor. And set expectations with your own behavior. If you always respond to messages in the evening and on the weekend, people will take that as the norm; if you don’t, then they won’t expect you to.

Nick also recommended keeping in mind that the more emails you send out, the more you’ll get back. So avoid the temptation to send “just one” response on a Saturday, lest you find yourself caught up in a back-and-forth that runs all weekend long. If you need to get a response off your mind, write it up, and then schedule it to be sent first thing Monday morning.

General George Marshall went on to create the Marshall Plan, rebuild Europe, and win the Nobel Peace Prize. He did all of it on eight-hour days with absolute focus, discipline, and a genuine understanding of human limits. He understood that a man’s effectiveness has a lot more to do with the quality of the work he does at his desk than with how many hours he sits there.

This article was originally published on The Art of Manliness.

I’m in my late thirties and have been laid off twice in my working years. This is not an unusual experience, especially in the post-COVID era, which some have termed a time of “forever layoffs.” Nearly half of all working adults have been laid off at some point in their career and most working employees are worried about layoffs on a regular basis.

The first time it happened to me was in 2012 when the small marketing agency that I’d been with for only a year went belly up. I was young, didn’t have many responsibilities in life just yet, and the job hunt went quite well; I secured a new gig within a handful of weeks. The second time I was laid off was in 2024, as part of a larger set of cuts at a billion-dollar tech company I had been with for about three years. Twelve years after my first layoff, not only was the economy wildly different, but I had a family, three young kids, and a mortgage to worry about. It took almost a year of ups, downs, and freelance projects to get back into comfortable employment. Those two instances ended up being pretty different experiences, and yet a similar set of tactics helped me get through both times.  

There will inevitably be a flood of anxiety after you’ve been laid off. But once your heart rate has calmed down and you’re able to move beyond panic mode, do these five things to get yourself in a good position to survive and move forward.  

Nail Down Your Financial and Insurance Logistics  

As hard as it can be in those first days after being let go, you need to start thinking right away about your finances and health insurance. It can be hard to do so without catastrophizing, but it’s important to think clearly and strategically about how you and your family will weather the financial unpredictability of the coming weeks and months.

Insurance

First, consider your insurance situation. Be sure that you have information from HR about when your benefits lapse — it can be immediate, but sometimes it’s a few weeks or even months down the road.

If you’re carrying the household’s insurance and have the option to move to a spouse’s insurance plan, definitely go that route, even if it’s not for the long-term. Having coverage is better than not having coverage.

If that’s not an option, COBRA is a federal government program that allows you to receive the same exact insurance you had with your former employer, for a period of 18-36 months after being let go. The major difference is that you’ll have to pay the entire cost of the premiums. If you’re in a field with good benefits, it may be exorbitantly expensive to pay out of pocket. In that case, your state’s insurance marketplace is where to look next. It can be confusing if you’ve never dealt with it before; your former employer’s HR department may be able to help you find a broker to help with that process. Don’t hesitate to ask them these types of questions.  

Finances

You also have to think realistically about your budget. How much do you have in your bank account? How much severance are you receiving, if any? How much do you have in emergency savings or other accessible accounts (that is, stocks or other investments that don’t have withdrawal penalties, rather than retirement accounts)? Make sure you know exactly how long you can make it without your income.

Next, apply for government unemployment benefits. Each state has their own online portal (and set of rules). You’ll be entitled to a percentage of your previous wages (typically 50%) for an entire year. It’s a hassle, and there are a lot of forms, including weekly online check-ins about your job search, but there’s no reason to not take advantage of unemployment checks. After all, your taxes have been paying into that fund for as long as you’ve been working!

Reach Out and Start Networking

Time to share some harsh truth: In today’s job market, it’s nearly impossible to just apply for a job that you found online and get invited to a screening interview, let alone make it all the way through the lengthy multi-interview + work test process that pervades modern job hunting. In the vast majority of cases, networking will get you farther than scrolling job listings online. It bears repeating: while networking does not necessarily have the same immediate ROI as applying for random jobs, it will net you greater returns in the long run.

In particular, it’s worth reaching out to your weak ties — those loose connections you made in college or through work or church. You aren’t quite friends with these folks, but know them well enough that reaching out in this scenario isn’t weird. Go creeping on LinkedIn to see where folks work; if a company seems interesting, there’s no harm in sending a message like:

“Hi there! I know it’s been a while since we’ve talked. I hope you’re doing well — I loved seeing that family picture on Facebook. I wanted to reach out and say hello because I was recently let go from my job of five years. I’m trying to get a feel for what the market is like and what’s out there and would really appreciate a 30-minute chat if you’re willing. If the timing isn’t right, no worries, but it’d be great to catch up a bit.”

If they agree to chat, don’t make it just about finding a job at their company; it really should be a broader focus on if they know of anyone or anything helpful. If you talk and something seems like a good fit, they’ll let you know. (After you talk, make sure to send a thank you note or message!)

Beyond those weak ties, also do some fresh networking both online and in your community. With a quick internet search, you’ll be able to find digital and IRL networks of folks in your industry. Again, the ROI is not always apparent, but genuine networking — with the goal of just getting to know people and getting your name and face out there — always has a way of paying off in the long run.  

P.S. This is a great reason to never burn bridges on your way out of any job.

Set Some “Working” Hours

In my observations, it seems that there are two types of responses to being out of work: either you can’t seem to get off the couch to do anything or you turn that anxiety into a kind of hyperactivity, spending every waking moment on the phone or computer. Both of those approaches have problems that can be remedied by doing your best to set daily “working” hours.

Don’t try to replicate a full work week; set aside 3-4 hours per day for networking, job hunting, building up your skills, and the like. The work of finding work is mentally taxing (and, let’s be honest, often defeating) in a way that a “real” job is not. There’s no psychological security at all; in fact, you’re mostly dealing with feelings of existential dread the whole time. As such, your willpower gets depleted rather quickly. After half a day or so, you’ll experience diminishing returns and it won’t be worth the additional mental energy to keep going. You can only scroll through so many job listings and write so many cover letters in a day before you start to feel your soul escaping your body.

Conduct Career Experiments

My initial response to being let go was, naturally enough, to apply for positions similar to what I just held. That makes total sense and should absolutely be your first plan of attack. Unless you have a sizeable financial cushion, it’s not a bad idea to do this even if you plan on changing careers — it may make for a nice fallback should that other route not work out as quickly as you hoped.

Within a few weeks, though, it was easy to blast through applying for the roles that most matched my resume. After that, I took the liberty of getting a little more creative and looking for roles that I wasn’t perfectly qualified for but suited my interests a bit more. Even though my career has been in online media and marketing, when I was laid off in 2024 I branched out and had a couple interviews outside my comfort zone, including with a small coffee roaster and a large airplane manufacturer. I even considered going back to school. I didn’t end up doing any of those things, but I thought long and hard about them and did learn a lot about what it would be like to jump industries, to start at the bottom of a workplace food chain, and the practicalities of starting fresh.

If you’ve ever thought of doing something different with your career, perhaps being let go is the spark you need to jumpstart that process. Don’t be afraid to look outside of what you know, especially if it’s an industry that’s been hit hard with layoffs (perhaps making it all that much harder to get a new job in that field).  

Do Your Best to Relax

One of the things that bothered me most — and which happened both of the times I was laid off — was hearing from folks about how I now had some time to sleep in, relax a bit, and enjoy “funemployment.” As if! There was no way I could sleep in or really even remotely enjoy myself while in the midst of desperately trying to find a way to replace that income as soon as possible. It’s very hard to relax when you’ve been laid off versus when you’ve left a job on your own terms, even if you’ve been lucky enough to receive severance pay.

That said, each time it’s happened to me, I forced myself to at least do some activities that would normally bring me joy — even if they didn’t immediately do so in the moment. For me, it was hiking/walking every day, reading, and doing some extra cooking/baking. While there’s a time and place for some true vegging out with Netflix, it’s best to shoot for a more active type of relaxation that comes from using your body and brain in a way that you get deeper fulfillment from. Regular exercise should especially be part of that routine. If you just lounge around on the couch all day, you can quickly fall into a pattern that’s hard to get out of.

It’s likely going to be hard to truly relax and let yourself recharge, but at least go through the motions. Some of it will stick and you’ll at least build up a good routine of caring for your mind and body while without work.

The job market and the process of finding work after a layoff is unpredictable. I simply cannot say that it will all work out in a timely manner. But if you follow these steps, you’ll at least have a better setup for success than you would have otherwise. Best of luck out there!

This article was originally published on The Art of Manliness.

In the years after World War I, longtime Army colleagues and friends George S. Patton and Dwight D. Eisenhower contemplated what would happen if another global conflict broke out. As Patton envisioned it: “In the next war, I’ll be the Stonewall Jackson, and you can be the Robert E. Lee. Ike, you do the big planning, and you let me go in and shoot up the enemy.”

And that’s pretty much how things worked out in World War II.

Eisenhower led from Allied headquarters as Europe’s Supreme Commander, while Patton served on the ground as commander of the Third and Seventh armies. 

Ike, who lacked battlefield experience, was nonetheless brilliant as a theater commander. Having spent his career as a highly effective staff officer, he had a genius for planning, marshaling material, organizing logistics, and practicing diplomacy. Charming, modest, flexible, and steady, he excelled at getting the disparate and sometimes rivalrous Allied leaders to work together, interfacing with politicians and the press, and keeping all the pieces of a monumental war effort sorted and spinning.

Patton, on the other hand, had little patience for politicking and wasn’t lauded for his ability to formulate high-level plans. But, he possessed all the traits necessary for superior battlefield command. Bold and aggressive, he executed missions with mastery and confidence and advanced with relentless drive.

While each man’s position and responsibilities were different, each excelled in his particular role.

Ike was the consummate strategist. 

Patton was born to be an operator.

Strategists Versus Operators

Andrew Wilson, a professor at the Naval War College, describes the difference between Eisenhower and Patton as the difference between having a bent toward strategy versus having a bent toward operations. 

Wilson defines strategy as “the means by which you translate political purpose” — what the political leadership hopes to achieve with a war — “into military action, and how it is that you anticipate military action to deliver your political purpose. . . . So strategy is the bridge between policy and military actions.”

Operations, he says, are those military actions — “essentially the big muscle movements, the battles.”

Those who excel in that second kind of work — operators — do best on the ground and in the field. They excel at, and derive satisfaction from, practicing and carrying out a certain skill, craft, or art.

Those who excel at the first kind of work — strategists — do best in high-level positions. They excel at, and derive satisfaction from, overseeing, organizing, and supervising those who practice and carry out skills, crafts, and arts.

Another way to describe the strategists versus operators dichotomy is as managers versus tacticians.

It’s a distinction in men’s proclivities that extends beyond the military context, and it’s crucial to know which category you fall into. 

Are You a Strategist or an Operator?

While there are a few men who are adept at both strategy and operations, most primarily lean toward one over the other.

Problems arise when men don’t have the self-awareness and foresight to understand their personal strengths and propensities, and end up in a role for which they are ill-suited.

Strategists Becoming Operators 

Sometimes a man is doing well as a manager type, but may desire a job in the field, perhaps because such work seems “sexier.” For example, he may have done well for years as a supervisor within a company, but thinks about striking out on his own and becoming an entrepreneur, even though the skill set necessary for success in the former pursuit isn’t likely to translate to success in the latter.

Eisenhower thought about making this kind of shift.

In the lead-up to WWII, Ike thought he’d like to work alongside Patton and become the commander of an armored regiment. He had never seen combat; because he was so good at training others, he had been kept stateside during WWI and tasked with preparing troops to deploy. Having missed out on the consummate experience of a military career during the First World War, he was determined to get into the field during the Second.

So when in 1941, a general in the War Plans Division asked Eisenhower to consider joining its staff in Washington, Ike demurred. He really liked the prospect of that position, and knew he’d do well there, but felt that a field command was something he was supposed to prefer. He felt conflicted, and worried he’d “pass[ed] up something I wanted to do, in favor of something I thought I ought to do.” 

Eisenhower needn’t have worried. While he continued to position himself for field command, his administrative abilities were too valuable to be dispensed with, and he was eventually appointed chief of staff to the commander of the Third Army, then Chief of the War Plans Division, and eventually Supreme Allied Commander. Ike’s sense of personal satisfaction, and the fate of world history, benefitted from his sticking to these strategic positions.

Operators Becoming Strategists

What happens more often than managerial men trying to shift into tactical roles is tacticians being promoted into administrative positions. Those who excel in operational roles are frequently moved up the ranks. The problem is, the skills required to succeed as tactical operators don’t typically translate into success as strategic supervisors. This is the essence of the “Peter principle.” And not only may a tactician placed in a managerial or executive job struggle to be competent in that position, he is also unlikely to enjoy it. 

Entrepreneurs who successfully launch start-ups often don’t transition well to becoming the CEOs who run them. Fitness coaches who excel at training clients frequently flounder at owning their own gyms. Pastors who have the skill set to plant churches don’t always have the skill set to oversee the large, established congregations they grow into. Doctors who like practicing hands-on medicine won’t be satisfied spending their days supervising teams of nurses. Academics who enjoy teaching end up less happy as deans than they were as professors. 

Writers and artists, who initially function as fully autonomous operators, sometimes try hiring assistants and social media gurus to expand the empire around their “brand,” but find they’d rather keep their “business” smaller than to give over any of the time they could be creating to managing other people. 

Sometimes an operator has to transition to being a strategist because the fieldwork they do is physical in nature and takes a toll on the body. As a man who works in the trades gets older, for example, he may find it desirable and/or necessary to move from working on projects himself to supervising the work of others. 

But oftentimes, an operator ends up in a managerial position because he feels he’s supposed to take it and defaults to following the standard professional trajectory. The next rung up the ladder may take someone out of the field, but the position comes with more money, power, and/or status. A man thinks he ought to keep moving up in the world, even if that “advancement” puts him into a position he’s less suited for and finds less fulfilling.

Do You Want to Be in the War Room or in the Trenches?

It’s important to know who you are: a strategist or an operator.

If you’re a manager type, lean into that, even if that job may not seem as sexy as others. Administrators are absolutely crucial in keeping the world spinning round, and even help win world wars. 

If you’re the tactician type, do some real reflection before you accept that “promotion.” Is the benefit in money and status worth the tradeoff in fulfillment that comes from doing a job you’re brilliant at and love? It’s okay to recognize that you like carrying out orders more than formulating them. And it’s okay to value the chance to practice the things you’re really skilled at more than a bigger office. 

When Eisenhower was serving as Allied Supreme Commander in North Africa during WWII, his forces experienced some initial setbacks on the battlefield, and the Army’s Chief of Staff, George Marshall, suggested that Ike bring Patton in to serve as his deputy and oversee the fighting. But Patton balked at the idea of taking a more administrative job. He understood that he could do more good on the ground than at HQ, and that an operator belongs in the field — not behind a desk.

With our archives 4,000 articles deep, we’ve decided to republish a classic piece each Sunday to help our newer readers discover some of the best, evergreen gems from the past. This article was originally published in January 2023.

This article was originally published on The Art of Manliness.

What if the traits you’ve been taught to suppress your entire career are actually the very qualities that separate those who get what they want from those who stay stuck waiting for recognition that never comes?

Today on the show, Jenny Wood argues that most of us are living in what she calls “an invisible cage” created by an overabundance of caution, and that the biggest lie you’ve been told in your career is to keep your head down and let your work speak for itself.

Jenny is a former Google executive who developed a career development program used by 56,000 people in nearly 100 countries, and she’s the author of Wild Courage: Go After What You Want and Get It. In our conversation, Jenny explains how traits that have a negative rap can be used for positive ends that will advance your career. We discuss how being shameless, reckless, nosy, manipulative, obsessed, and more can help you overcome your success-hindering fears, take bolder action, and achieve your goals.

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Brett McKay: Brett McKay here, and welcome to another edition of the Art of Manliness Podcast. What if the traits you’ve been taught to suppress your entire career are actually the very qualities that separate those who get what they want, from those who stay stuck waiting for recognition that never comes? Today on the show, Jenny Wood argues that most of us are living in what she calls “an invisible cage” created by an overabundance of caution, and that the biggest lie you’ve been told in your career, is to keep your head down and let your work speak for itself. Jenny is a former Google executive who developed a career development program used by 56,000 people in nearly 100 countries. And she’s the author of “Wild Courage: Go After What You Want and Get It.” In our conversation, Jenny explains how traits that have a negative rap can be used for positive ends that will advance your career. We discuss how being shameless, reckless, nosy, manipulative, obsessed, and more can help you overcome your success-hindering fears, take bolder action, and achieve your goals. After the show’s over, check out our show notes at aom.is/wildcourage.

All right, Jenny Wood, welcome to the show.

Jenny Wood: Thanks so much for having me, Brett.

Brett McKay: So you were a successful Google executive. While you were there, you also developed a career development program that helped employees advance their careers by learning how to advocate for themselves, stand out for the crowd. So you’ve made a career for yourself by being unapologetically ambitious, like going after what you want. Have you always been like that? Were you like that as a kid, or was there a moment in adulthood where that switch finally flipped and you’re like, all right, I’m gonna start turning my ambition into action?

Jenny Wood: Ooh, there was a moment, Brett. There was a moment, and it was in 2011 on the New York City Subway, when I was riding the subway home from work, and about 20 feet away from me stands this really good-looking guy, gorgeous blue eyes, thick brown wavy hair, the whole works. And even though I wanted to talk to him, something held me back. The things you would normally think about some stranger on the subway. What if he’s a convicted felon? What if he’s married? What if 100 people stare at me on this packed train? So I sit there, I do nothing while the train passes stop after stop after stop, and his life, frankly, passes me by. But I’m so taken by him that I make a deal with the universe, and I say, if he gets off at my stop, then maybe I’ll try to strike up a conversation with him. And if not, c’est la vie. Well, he gets off at the next stop, which was not my stop, and just as the doors are about to close, I feel this wave of wild courage wash over me and push me out of my subway seat and off the train.

I chase to catch up with him, tap him on the shoulder. I say, excuse me, I’m sorry to bother you, but you were on my subway and I thought you were cute. You’re wearing gloves, so I can’t tell if you’re wearing a wedding ring, but in the event that you’re not married, any chance I could give you my business card? And then I wait for what feels like forever for him to take my card, thinking this was a terrible idea. But he does take the card. He calls the next day. We go on a date a week later, and we’ve now been married for 11 years with two small kids who are nine and seven.

Brett McKay: No, I love that story. I love how you started your book off with that story, ’cause that really captures the title of the book, Wild Courage. So what were you like before that moment? Were you sort of just someone who played it safe, tried to stay in the background?

Jenny Wood: Yeah, I was a confident Google employee on the outside, but scared and timid on the inside, always worried about what my boss was going to think about me walking out of our Tuesday one-on-one, always concerned that nobody would forget that one client presentation I flubbed, always nervous about when I eventually had direct reports and indirect reports as a Google exec, what they thought about me and how they were gonna score me as a leader at Google because there’s a lot of upward and sideways and downward feedback at Google. And it’s funny, just yesterday I gave a keynote to a Google team that happens to be led by the guy who hired me at Google almost two decades ago. And he’s like, Jenny, it’s so interesting and wonderful to see you come into your own because when you first started, you had a hard time having a perspective. You had a hard time sharing your thoughts. I knew that you had smart ideas, but you were too nervous and timid and held back to share those out loud for business impact. And I was like, wow, it’s so interesting because sometimes I think people push back on me and they’re like, it seems like you were just born this way, Jenny.

You seem really confident. You could sell ice to Eskimos. And it was such an interesting moment when I was doing this talk and getting this feedback from the guy at Google who hired me to realize like, yeah, I was not born this way. And you don’t have to be either. You might not be a subway chaser, but wherever you are sitting right now, there is something that you want. And wild courage is what closes the gap between what you want and what you get. And it’s this set of tools that help you go after those things and get them. And it can be learned. It is not an innate skill. It takes practice, it takes reps. It takes building the muscle of wild courage.

Brett McKay: And as you described yourself in the book before you made this jump to wild courage, you remind me of, I was like this in high school too. Correct me if I’m wrong. This sort of describes you how you were in high school and college. You worked hard, you were quietly ambitious, you kind of just like, I’m gonna work really hard, do my best, and then I’ll just wait for people to notice.

Jenny Wood: Yeah, exactly.

Brett McKay: And then if people notice me, then okay, that’s fine. But if they don’t, I’m just gonna stay in the background. I think there’s a lot of people like that. They’re really conscientious. They do good work, but they wait for people to notice before they actually put themselves out there.

Jenny Wood: Absolutely. I was like that. I would almost take it a step further and say that I was really hesitant to stand out, even to acknowledge my own ambitions or share them.

Brett McKay: Yeah, you have this great line in the book that says, “Most existential anxiety in life isn’t about a lack of ambition, but an overabundance of caution.” So the book’s called Wild Courage. What makes wild courage wild?

Jenny Wood: Well, wild courage consists of nine traits that create the bars of an invisible cage that keep you small, that keep you quiet, that keep you following instead of leading. And my goodness, do they raise eyebrows. They are weird, selfish, shameless, nosy, obsessed, manipulative, that’s a spicy one, brutal, reckless, and bossy. And those are not traits we typically think we want to aspire to. So that is the wild piece of it.

Brett McKay: Okay, so your traits of wild courage are weird, selfish, shameless, nosy, obsessed, manipulative, brutal, reckless, and bossy. And what you do in the book is you reclaim these words, which they typically have a bad rap, and you reframe them with new definitions and lay out how they can be used for positive ends. And you say people can use these traits to overcome the three fears you think hold people back. It’s the fear of failure, the fear of uncertainty, and the fear of judgment of others. So let’s talk about some of these traits. The first one is weird. This is all about standing out. Why is learning to stand out such an essential skill and trait to develop if you want success in life?

Jenny Wood: Yeah, well. The world is just too busy and competitive for you to be invisible and make a dent in your career or in your life. So weird is about having the courage to stand out and be authentic, because within your so-called weirdness lie your greatest strengths. So hone every ounce of weird you’ve got. And that might be what I call playing it hot, which is respectfully disagreeing with your boss in a one-on-one, or sitting in the front row of your VP’s presentation, or being the first person to raise your hand and ask them a question. Or actually, you referenced this program I started at Google called, Own Your Career. That was kind of weird. I played it hot. I did not ask for any permission. This was not my full-time job. I ran an operations team that sat between sales and engineering and helped drive billions of revenue for the company annually. But people would come to me for mentorship, and this guy came to me, and he was asking, he was one of the many people who came to me for mentorship, and was asking, hey, how do you navigate entry-level to executive here?

And I was like, okay, let me just scale this. Let me write down 10 tips that made me successful here, everything from navigating politics, to stakeholder management, to influence skills, to getting promoted. And I’ll just put together a quick training. I’m sure that maybe 30 people will come. Well, 2,000 people came to that first training, and that grew into Own Your Career, which was used by 56,000 people in nearly 100 countries. But here’s the thing. I was playing it hot. I was being weird. I was not in HR. I was not in people operations. I just decided to go for it without asking for permission from anybody, or running it up the flagpole, only for it to die in committee of approvals. I didn’t ask HR, I didn’t ask legal, I didn’t ask comms. And then all of a sudden, I was writing emails that went to 56,000 people at Google. So it’s ’cause I played it hot. I just went for it, and I begged forgiveness, not permission. And there are so many smart, talented people sitting on brilliant ideas that never see the light of day, because they’re waiting for permission or waiting for perfection, quite frankly. And they don’t just start and put something out there like 10 bullets on a document, hoping that maybe two dozen people will come, and then it ends up being a lot bigger than that.

Brett McKay: All right, so being weird is about embracing your quirks, sharpening them into strengths, standing out in a good way. It’s all about leaning into what makes you unique. And then playing it hot is a stance towards life where you show up with your weirdness, with boldness, and energy instead of trying to play it cool and blend in. There’s risk with this though, with playing it hot, ’cause people could just think you’re weird in an off-putting way, or you might step on some toes. But the benefits will typically outweigh the risk.

Jenny Wood: Yeah, let me touch on that for a moment, ’cause this is critically important. When I was launching this book, Kim Scott was a big mentor of mine. She’s like, “Jenny, this is your time to beg.” This might fall a little bit more into the selfish or shameless trait, but she’s like, “This is your time to beg.” I had built relationships with a lot of authors and influencers, and I asked maybe 100 of them to help promote the book, whether it was sharing it on social media or on their blog or if I could be on their podcast, or it was actually probably closer to 200, or whether they’d write a newsletter about it. And there was one very, very famous author, and if I said the name, I will not for their privacy, but if I said the name, every single one of you would know it. And this person not only said no, but also ended our friendship and our mentorship relationship, and man, did it sting. I lost sleep over it. This was just a couple of days before a pub date, and it was a time when I needed to not be losing sleep, and it stung.

But if I had used that rejection as an indication to just start playing it cool and not asking for help or not being weird or not shamelessly putting myself out there, then this book would not have been nearly as successful as it has been. And so, even though the outcome wasn’t what I would have wanted, and it really felt like a punch in the gut, and it still hurts to this day, it still hurts to be told no from someone you deeply respect and admire because you’ve played it too hot. But it doesn’t mean that the decision was bad. It was just the outcome that wasn’t ideal. And so, I still carry that play it hot mentality with me because, 80% of the other people said, “Yes, we’d be thrilled to help.” And then 20% said no respectfully. And this was like the one outlier who said no, in a way that was painful for me. But it’s okay, because we push past those painful moments and we keep doing great things.

Brett McKay: Besides playing it hot, another way you suggest you can be more weird is sharpening elbows. What do you mean by that?

Jenny Wood: Yeah. Well, this is an example of when I was at Google, and the most senior leadership team, kind of the equivalent of the C-suite of this org of Google, was meeting in London to decide a reorg and the fates of the people below them. Now, the people below them, myself included, were not invited to London for the actual meetings. But lo and behold, a bunch of us showed up in London to rub elbows. It’s like call, sharpen our elbows to be in the same proximity, to have coffee chats, to be present. And again, if you wanna be invisible, you can, but it’s not going to help your career because being in the same room, if you’re not invited, if you don’t have a seat at the table, bring a folding chair, as they say. But I think just showing up makes a big difference. It’s like the classic line, 80% is just showing up. And it was astonishing who decided to fly to London and who decided to not and what the outcomes looked like. Because politics are real, relationships are real. And again, it goes back to the biggest lie you’ve been told in your career is just keep your head down, your work will speak for itself. It won’t.

Brett McKay: At the end of each chapter, you have a section of what you call trait traps. And this is how the quality you’re talking about in that section can turn into a weakness. And for the weirdness section, you say the trait trap there is when you start thinking of weirdness as being rude, annoying, just obnoxious. So the takeaway for weird is that you wanna be weird in a good way. Just by doing the things that other people aren’t doing, doing things that might be unusual or unusually bold, just standing out from the crowd. But it’s in a good way. You’re not being obnoxious about it. Let’s talk about another trait, and that is selfish. Nobody wants to be known as selfish, but let’s talk about this first. How can selflessness be harmful? I think that’s a good way to start this question.

Jenny Wood: Yeah. Well if you give everybody a leg up at your own expense, you’ll end up getting trampled. So start showing up for yourself. I redefined this as the courage to be your own champion. And even when I was running the, Own Your Career program, I feel like I took my eye off the ball on my core job a little bit, and I was almost over-delegating to the leaders who reported to me. And then, I had one conversation with my manager who was basically like, Jenny, get your eye back on the ball on your core job. And then it even meant that I had to kind of reshift some of the priorities to either peers who I delegated to or direct reports because I had to look out for myself. I needed to maintain a good performance course that I could continue bringing this good work to the world. And it’s tough. It’s tough, especially as a leader, to be selfish and say, my career matters too. But at the end of the day, I deeply believe that as much as your manager is supporting you and your career, they’re gonna put their career first.

And they should, because if we’re not showing up for ourselves, then who is? And for the parents out there, you might say, oh, well, if I were to ask you the question, who’s more important than you? Start showing up for yourself. And if you were to say, oh, my child is more important than I am, but does your child need a martyr who’s exhausted and depleted and hungry and sleep deprived? No, go to that yoga class, go to that golf, Sunday regular session that you do with your buddies, and take the time that you need so that you can replenish and show up for the people in your life in a thoughtful and intentional way.

Brett McKay: So being selfish actually allows you to serve better?

Jenny Wood: Yeah.

Brett McKay: Yeah. So what does positive selfishness look like for you?

Jenny Wood: Well, it’s saying yes to the big and no to the small, at least in a work context, but also in a life context. So what’s big? The Q2 strategy project that your C-suite really cares about. What’s big? Improving customer satisfaction by 12% quarter over quarter. Again, in a work context, what’s small? Being the 18th person to reply all on the happy birthday Jimmy email. Give him a high five when you see him at the water fountain. What’s small? Attending every single meeting where you neither add value nor derive value. And how often do we do that? And what’s small? Being the person who always takes notes in the meeting or always raises your hand to lead the wellbeing pillar. Like, yes, these things are good for community, for culture building. Yes, it’s nice to occasionally plan the company picnic for the summer. But if you did it the last several times, if you took notes the last several meetings, then those small actions constitute what I call nap work, not actually promotable. So avoid more than 10% nap work. Because no one ever gets promoted for being responsive to email. And yes, do a little bit of it.

But if you notice that you’re dialing up to 30%, 40%, and granted this stuff can be easy, it can be simple. Sometimes it avoids the big scary projects of the customer satisfaction increase. But if you do too much of it, it’s just not gonna serve you well. So I say don’t nap at the office because you wanna do the big work that moves the business, because what moves the business is what moves your career. And same thing in your life at home also. Like, what are the things that you need to respond to on a given day and what are the small things you can avoid? And maybe it is not responding to every text that comes in, right?

Brett McKay: Yeah, that nap work, I can see that can be a trap for people in their career. ‘Cause often nap work, it’s easy and it’s concrete and it’s actionable. It’s like, oh, I’m doing something. But if you look at it, it doesn’t really move the bottom line on things. And so, I can see it can put someone in a position where like, I just do so much for the company. No one appreciates what I do, but you’re doing stuff that, it’s nice, but it’s like not necessary.

Jenny Wood: Yeah it invites more work, but it doesn’t invite more responsibility.

Brett McKay: Yeah, so say yes to the big, no to the small. But a lot of people have a hard time saying no. Any advice for people who have a hard time saying no to that sort of rinky-dink stuff because it makes them feel bad?

Jenny Wood: Yeah, so two tools are the agenda avenger and the power postpone. ‘Cause nobody wants to say no, and then feel like a jerk. But there are so many ways you can say no and not feel like a jerk. In fact, I do have a freebie if people wanted it. It’s @itsjennywood.com/sayno. It’s eight scripts tools, tricks to say no to meetings, projects and favors, because we get them all the time and we feel guilty. We don’t have the wild courage to say no. And then sometimes a yes turns into like 20 other yeses. It’s like, can you do this quick thing? Okay, cool. Now can you schedule this thing as a result of it? Oh, we’ve got to reschedule it. Now we’ve got to inform this one person. So one little yes can turn into 20 different yeses. But you can use the agenda avenger, which is, let’s say for example, someone asks you to hop on a call. You could say, I’d love to get a better sense of what you wanna cover. Could you send a quick agenda first?

If you push back, and that’s why it’s the avenger, the agenda avenger. If you ask them for an agenda, they’re gonna have to think real hard if you really need to have that meeting. And by the time they put together that three, five point agenda, they might just realize that can be solved over email. How many times have we been in a meeting that really should have been an email? And then, another one is the power postpone. So I’m planning to take a sabbatical coming up here for six weeks. And so, that’s a natural power postpone where I say, I can’t meet now, but I can meet in about eight weeks. And then, sometimes it just resolves itself. Or if they really, really wanna have that meeting or have you on that project, then they can wait. But oftentimes, it just disappears. And those are two of the eight very practical tools I share with people to thoughtfully say no without feeling like a jerk.

Brett McKay: Yeah, the asking for an agenda, I’ve used that a lot in my career. So I’ll get people who will email me like, “Hey, I got this thing. I’d love to hop on the phone to talk about how we can partner together.” And it’s like, what does that mean? Okay. So I send an email like, hey, this sounds great. What are some concrete ideas you have right now on how we can partner? And then they’re like, oh, I don’t know. Okay, well, once you have some ideas, maybe we can hop on the phone then. But when their ask is kind of vague, it’s like, well okay, I’m gonna have you be a little more specific so we can figure out if there’s actually something here for us to do.

Jenny Wood: Yeah, definitely. Or another version of it is, I’d get tons of people who’d reach out to me and say, “Hey, my nephew would love a job at Google. [laughter] It’s always someone’s nephew would love a job at Google. Another strategy here is yes, if, or yes, when. Yes, we can do that if you put together three job recs that look interesting to you. Or yes, we can do this when you send me your idea of the perfect job or something like that. So again, it’s similar to the agenda avenger. You’re not specifically asking for an agenda, but you’re saying, yes, we can do it if you do this or when you do that. So yes, if, or yes, when, to also see if that meeting really needs to happen.

Brett McKay: Another tactic you have for being more selfish in a positive way is winn. W-I-N-N. What’s that?

Jenny Wood: I love this one. I’m so glad you’re bringing it up. So this is play to winn. What I need now, W-I-N-N, as you said. And this is about being selfish about how circumstances might change. And there’s this wonderful story about a session singer for Pink Floyd named Clare Torry. A session singer is someone who is hired for a very small fee to come in and sing backup vocals or something as part of a track for one individual song for a band. So in London, Clare Torry came in and she was paid 30 pounds to sing these backup vocals for the great gig in the sky on a Pink Floyd album. And so, she collected her 30 pound fee and went home and didn’t even know that the song had made the album until it came out. Well, it turns out that album went 14 times platinum. A little bit more than, and her vocals are legendary. If you know the song, it makes the song. And so, she played to win. She said, what I need now is to sue Pink Floyd and ask for a much significant part of the royalties and a songwriting credit.

And then she was really smart and selfish to do that. And Pink Floyd was smart to settle out of court for an undisclosed sum. So what might that look like for you? Maybe your company has just gone through a reorg or layoffs and you’re now doing the job of two people and you’re overworked and overwhelmed and feel like you’re underpaid. Well, what I need now might be giving yourself the advice that you might give to a friend, which is put together three slides, go to your manager, explain the work that you’re doing, ask for a new title, ask for a raise. And we selflessly say things like, oh, but I’m just happy to have a job. Or, what about Alan and Sarah and Louisa? They’re doing hard work too. What about their raises? Well, being selfish is standing up for yourself. And sometimes what I need now is the permission we need to recognize that it’s okay to ask for something when the circumstances have changed.

Brett McKay: Yeah companies or CEOs, they play to win.

Jenny Wood: Heck yeah, they do. And that’s why they’re so successful.

Brett McKay: Yeah, if they never think, well, we promised this guy this job for a long time. It’s like, well, okay, the situation now is like, we’re losing money and we have to make cuts to keep this company afloat. That’s the situation now. So we got to make the cuts, I’m sorry. It’s not personal or anything. They’re playing to win.

Jenny Wood: Yeah, one of my best managers, Mike, said to me in a one-on-one when I was really being a workaholic and not taking any vacation, he’s like, “Jenny, you are capped out on vacation. When is your next vacation gonna be? I’m worried you’re gonna burn out.” And I said, I know, Mike, I’m just so passionate about this project and this new team. And I just, I love Google so much. And he was like, I think about my saying this and like what a ridiculous, it’s not that, Google’s an amazing company. Don’t get me wrong, but what a funny thing to say to justify me not taking vacation. And I will never forget his retort back. He said, “Jenny, that is great. But I want you to remember that Google doesn’t love you back.” And just like you said, Brett, they’re gonna be selfish. Any organization is gonna be smartly selfish if there’s a financial crisis and they have to have a RIF, a reduction in force, if they need to shift priorities and take a big project away from you, if they need to freeze hiring, if they need to pause promotions or give lower raises or bonuses, they will be selfish left, right, and center.

So you can be selfish too, but there’s this power imbalance. Where we look to our companies or we think that our boss’s boss has so much authority and that we can’t ask for what we want, but the best leaders, the future leaders are the ones who ask for what they want because you’re displaying future leadership skills.

Brett McKay: Are there any trade traps with selfishness?

Jenny Wood: Yeah you want to, with all these traits, be expanding the pie and not re-dividing the pie. So I do advise people to look for ways that are mutually beneficial as opposed to, for example, when I needed to be a little bit more selfish about my career and kind of get my eye back on the ball, if I was going to insert myself more in a project that I delegated to a peer or a direct report, I would think about something else that they could do that would bolster their profile as well.

Brett McKay: We’re going to take a quick break for a word from our sponsors. And now back to the show. All right, let’s talk about shameless and shameless. This is all about leaning into your strengths and not being afraid of showcasing them. It’s all about having some swagger.

Jenny Wood: Yeah.

Brett McKay: What do you think holds people back from promoting themselves?

Jenny Wood: I think that this is the biggest challenge with Wild Courage. I do. I think that people feel insecure. They feel rife with imposter syndrome. They feel like they don’t deserve it as much as somebody else. They feel like they don’t have the skills that somebody else has. But there was a moment in a meeting that I was leading where there were maybe 20 people in the room and this guy came in and he’s like, “This is a shameless plug, but I put together this spreadsheet that might help you.” And he shared it over the group chat. The emojis go flying. The chat explodes. Oh my gosh, this is gonna be so helpful. This is gonna save me 20, 30 minutes every time I need to create this project proposal for clients. And yet he led with, this is a shameless plug. And it’s like, what’s the shame in that? You’re sharing something useful and helpful and a time saver for people. And yet we hesitate to share our wins. And I think one of the most helpful tactics here, is to make it consistent, make it a system. If, for example, you shared every Monday what I call a shameless Monday email with your boss with four bullets, two things you’re proud of that you did last week and two things you’re excited about for this coming week, that is so powerful.

First of all, it makes it a lot easier to put together your performance review at the end of the quarter and your accomplishment bullets. But it also just systematizes talking about your wins and it becomes more natural. It becomes more of an update. There’s huge positive externality of then they might CC their boss. Or if you’re a leader, you could share this with your team and CC your own boss. And then you’re sharing with your team your priorities, which people love to know what their boss is up to that day. So the shameless Monday email can be really effective as you lean into your strengths and not be afraid to showcase them.

Brett McKay: Yeah, that’s a powerful idea ’cause your boss has no clue what you’re doing. He might have a little bit of a clue, but he probably doesn’t know everything. So this just makes it more explicit.

Jenny Wood: Yeah, definitely.

Brett McKay: You also have the power portfolio. What’s that?

Jenny Wood: Oh, I love the power portfolio. So the power portfolio is made up of your power assets. And just like a financial portfolio, you wanna have a mix of soft skills and hard skills or of business skills and people skills like you’d wanna have a mix in your financial portfolio of stocks and bonds. So these are the three strengths you have or the three things that you bring to the table that can move the business forward. So I had a coachee named Martina and she came to me with three power assets. She said, “Mine are communication, organization, and supporting others on launches.” And these were okay, but they needed tweaking because again, we want a mix of business and people skills. So yes, people skills matter, but managers and leaders want to know what business problems you’ll solve, because that’s what their boss is grading them on. So that’s why you wanna diversify your power portfolio and aim for a mix here. So we tweaked it. So communication became executive communication. Organization became project and program management, which she was phenomenal at. And supporting others on launches became go-to-market strategy.

Again, same ideas, different word choice, higher impact, shameless, right? But it’s just being more powerful in your language. And again, like organization versus project and program management does have a very different je ne sais quoi. To me, organization sounds weak. It sounds feminine. Not that that’s a bad thing, but in the context of wanting to show your leadership skills and show more of the value you bring to the customer, project and program management just sounds a lot more powerful. And so, we strengthened them by doing that exercise. But even aside from your specific language choice, a lot of people, don’t know their strengths at all or their talents and can’t articulate them in a bit of an elevator pitch. Like some people might just draw a blank if I say, what are the three things that, often I will say execs draw a blank when I say, what are the three things you bring to your team? And they really have to think about it. So it requires writing down maybe 20 things that you think you are pretty good at, things you’d love to do as a child, things that you’ve helped move the business forward on in the past. It might require bringing them to a coach or a mentor or a boss and triangulating it with other people think, and then you can whittle it down to three.

Brett McKay: And I imagine after you whittle it down to the three, you need to figure out what are some things that, like concrete things I can show, that showcases that I have these traits, be able to show that to people. Hey, I’m great at this thing. Here’s what I’ve done.

Jenny Wood: Oh, absolutely. If you’re talking about these in a resume or again, an accomplishment bullet, preparing for a performance review or promotion, you want to use what I call ROI, not the classic ROI return on investment, though this does give you return on career investment. It’s role, objective, and impact. What was your role in this go-to-market strategy? What was the objective? You wanted to launch the product with 10 million users in the first year. And what was the impact? You exceeded that goal and launched it to 11 million users in the first year. And also double your numbers. In any context, double your numbers. Or even going back to… When I say double your numbers, I mean in that example, I used 10 million. Maybe you could say 10 million by day 90. Use physical numbers. It is so much more powerful. They don’t have to be fancy, like revenue growth percentage or actual dollars. It could be, I cut this email sequence down for onboarding new clients from five emails to three, making it more efficient. Or I’m 70% of the way through the fall athleisure line competitive analysis.

Even just saying, I’m 70%, or I cut this down from five emails to three, has a big impact on showing the concrete, the tangible value that you bring to the table. So double your numbers anywhere you can, whether it’s in your shameless Monday email or a resume or accomplishment bullets or your power portfolio when you’re talking about your strengths in the specific situations with ROI where you demonstrated these power assets.

Brett McKay: How are you being shameless with the promotion of this book you’re doing?

Jenny Wood: Well, a big part of promoting the book is having companies buy the book in bulk. So there are books that are sold one at a time, and there are books that are sold 500 at a time. Because this book is so much about, it’s about wild courage in all areas of life, but there’s a bias toward professional wild courage and really thriving within your company, within your organization, and not saying, hey, go quit your job and be a solopreneur, be an entrepreneur. It’s really helping you feel engaged, feel happy, feel successful, feel motivated within your organization, which companies should love and want to buy. So I think this has the potential to be the kind of book that people buy 500 at a time. So how am I being shameless? I recognize that opportunity, and I sent about 300 emails to leaders, friends, acquaintances, secondary connections, subject line, are you interested in buying 200 copies of Wild Courage? And then I put a bunch of details. I’d happy to do a 20-minute complimentary fireside chat if you did. And I sent the first 100, and Brett, I thought that by the end of the day, those checks would just be rolling in for those bulk purchases.

But as it turns out, the budget is not always there. The timing’s not always right. There was a lot of ghosting, a lot of rejection. So shameless in this context is having the courage to just keep going despite all of that rejection. And this was different than the rejection of the one person who cut off our friendship. This was rejection at scale because there were so many people. I probably didn’t hear back from 90% of the people in that first 100. So what did I do? I tweaked the offering. Rather than 200 copies in the subject line, I put 50 copies. Rather than overwhelming them with too much information about the details of how this partnership could work and me coming to do a fireside chat, I whittled it down to just a few sentences. So you can use that rejection and tweak, dial your shamelessness up and down to what might better appeal to the audience.

Brett McKay: Well, this kind of ties in nicely to one of the other traits of being reckless. Like you’ve been reckless with your being shameless.

Jenny Wood: Yeah.

Brett McKay: Let’s talk about that. What does healthy recklessness look like?

Jenny Wood: Well, it’s the courage to err on the side of action, because better to learn from your mistakes than waste time predicting the consequences of every decision. Think fast and fearless. And if you’re on the fence, do it. And for all of you overthinkers out there, for all of you pro-con list makers and like me, left-brain thinkers who are in a lot of analysis paralysis, just thinking about like, what’s the worst that could happen. Even leaving Google for me took a lot of recklessness. And it was hard for me to get to the point where I knew I wanted to leave. And that was a moment where I felt my eyes fluttering closed when I was driving my son back home from choir practice because I had just taken on too much. I had my day job. I was running the, Own Your Career program. There was all this external interest that was budding about my work, including this book. And I was also trying to be a wife and a mom. It’s like five roles. And I was exhausted. I was struggling with lowercase a anxiety. I was oftentimes up between 2:00 and 5:00 AM. And I just was totally sleep deprived and physically, emotionally, and mentally unwell.

And so, I reached the moment where I felt my eyes closing as I was driving Ari home from choir, that it was probably time to go. But it took me about 12 to 18 months to muster the courage to do it. And that’s ’cause I wasn’t reckless enough. And so, I think I was caught in truths and tales. Truths are facts. They’re verifiable facts. This microphone I’m speaking into is black. I’m holding a piece of paper in my hand. But tales are the stories we tell ourselves to make sense of the facts. And so, part of recklessness is separating the truths from the tales.

And so, I really struggled with that leaving Google. The tales I told myself were, I’m gonna have no identity if I leave Google. Another tale, what if we run out of money and have to move out of our house in Boulder by all the trails that I love so dearly? Another tale I told myself is my parents are gonna be disappointed in me because I’m the breadwinner for my family. But then, when I broke it down to actual truths in that situation, a truth would be, yes, I’m not gonna get a paycheck every other week with the Google logo on it.

A truth would be, I can find other ways to have a new identity. A truth would be, my parents have always supported me and are supportive of me leaving Google as well. So that helps you be reckless when you separate the truths and the tales and really break it down to fact versus fiction.

Brett McKay: So another thing you talk about in this reckless section is this react framework. What’s that and how can that help you overcome failures so you can maintain that bias towards action?

Jenny Wood: Yeah, well, sometimes failures are not big colossal, I lost the project or I lost the deal. Sometimes a failure is just a moment that happens that’s cringeworthy during the day. And we’ve all had those. And one of mine was when I sent an email intended for six people to, I think it was 23,000 people at the time. That’s how big Own Your Career was at the time. And I sent it instead of to the volunteers working on Own Your Career, I sent it to the entire Own Your Career alias. And Brett, this was an unintelligible email. It was just a subject line that was three sentences long with nothing in the body. And it was a testimonial of someone who had said they loved the Own Your Career program and that they’d gotten promoted as a result of it. And so, the subject line was just TT: Atkinson Me, which is the person’s name, but it’s a really unusual name. And then I had typos in the subject line. And this went to 23,000 people, including many in the Google C-suite. So I was mortified. I pressed send and then I slowly dragged the mouse to the unsend only to not get there in time.

And here’s what happened. So React is how I overcame that horrible moment of mini failure. It stands for recognize, empower, apologize, celebrate, and trust. Recognize that not everything you do will be perfect. E, empower yourself to own it quickly and clean it up. Take a deep breath. It happens to everyone. And so, I really just had to put on my big girl pants and say, I can clean it up. I can recover from this. Then I did. A is for apologize. I directly apologized to TT. She was not intending for her feedback about Own Your Career to get broadcast to 23,000 people. C is for celebrate. Celebrate the unexpected goodness that comes out of a mistake. I got hundreds of pings and emails back, and not a single one of them said, you jerk, I can’t believe you distracted me with this nonsensical subject line. No, everybody was checking in on me. Everybody wanted to take care of me. Everybody wanted to help me and empathize with me. And they all said things like, Jenny, I promise nobody cares about this, like you do. Nobody’s paying attention. Everybody understands this. It happens to everyone.

They were so empathetic. So that’s celebrating the unexpected goodness that comes out of a mistake. And that’s also the T is trusting that your fellow employees will have your back. And by the way, the other part of C, celebrate the unexpected goodness is, I wrote up this react framework. I then shared it with the whole Own Your Career alias and said, here’s how I recovered from this mistake. And it ended up being the most popular tip of all time that I had ever sent. So it just goes to show you that you can make lemonade out of any lemon. And that’s the react framework.

Brett McKay: All right. So reckless, just take more action, have a bias towards action, and you can overcome those little setbacks and failure. It’s not a big deal. It’s not gonna be a career ender for you. Another trait is being nosy. And I love this section. ‘Cause you start off that section talking about how your grandmother was nosy and how that probably saved her life during World War II. What happened there?

Jenny Wood: Yeah. So my grandmother was in hiding during the Holocaust in Budapest, Hungary. And she left to get a bucket of water for the other people in hiding with her. And she walked down the street and somebody from the Arrow Cross Party, which was sort of the Nazi equivalent ruling party in Hungary, rounded up her and some fellow Jews at gunpoint. And they marched them to a building and they had them against a wall. And my Bubbie, my grandmother, I called her Bubbie, knew that there was no getting out of this. She was doomed. The options were, basically she was gonna get marched onto a train and taken to Auschwitz, like so many other people had, or she was gonna have a summary execution and get shot right there against the wall. And there were literally dead bodies in the street when this was happening, as she told the story to me, in Hollindale, Florida at the age of 93, when we were recording her Holocaust survival stories. And her only option, she told me, was to get nosy. And so, she asked the soldier, this scared, terrified, timid soldier, a question.

And she asked, what would happen if I were to step out of line? And she wasn’t necessarily looking for the answer. She was looking for his reaction. And he answered with the Hungarian idiom, which I will translate to English, which equals, is the mademoiselle so stupid or just pretending to be? And it was a little bit of a jokey answer. She saw a lightness in his voice. He almost cracked a smile. And she really saw his nervousness. And it made her realize that she had a small window here to step out of line, because he didn’t yell at her. He didn’t hit her with the gun. He didn’t cock the gun. And so, just by being nosy, having the wild courage to ask a question, it was the only way she was able to survive that scrape. So she stepped out of line and started walking down the cobblestone street. And she said she remembered hearing the click of her heels every time she took a step as she just kind of slowly breathed in and breathed out and hoped that nothing would happen. And it didn’t. And she returned back to the attic safely. And so, she really only survived because of her nosiness, because she had the courage to ask a question.

Brett McKay: So this is all about asking questions, what it means to be nosy. Why do you think people have a hard time asking questions in their career?

Jenny Wood: We think it makes us look stupid or uneducated or unknowledgeable. Or think about how many times, for those of you who work in an organization that has a ton of acronyms. You think, oh, well, it’s too late. I’m already in this role for four months. I can’t ask that basic question. I can’t ask that simple question again. But nosy is the courage to get insatiably curious because curiosity drowns out fear and pulls you toward what is most exciting to you. So use it as a compass. And curiosity shows leadership, it shows ambition. It’s a great way to overcome nerves at a networking event rather than feeling like you have to impress somebody. Go ask them a bunch of what and how questions like, what was the most interesting session for you so far? Or how long have you been in the industry and what brought you here? Or how have your peers been responding to these sessions? Or how are you using AI right now? What and how questions are so powerful and they take the pressure off of you in any kind of new relationship or networking situation or a meeting with a mentor where you feel like you’ve got to be all buttoned up and prove yourself.

Just start asking and start listening. And even the best leaders, going back to the person who’s a few months into the role and they’re like, oh, I’m too far in to ask what that three letter acronym stands for. But the leaders who we admire most are the ones who have the confidence, the shamelessness, the boldness, the recklessness to say, “Hey, what does PRT stand for on this slide? I just wanna make sure that for everybody in the room who’s new, we redefine that.” And everyone sighs a sigh of relief that somebody finally, had the boldness to redefine that acronym of the thousands that are used at the company. And when it’s a leader who does that, I really admire it.

Brett McKay: You also talk about how you can use nosiness or asking questions to turn envy into a springboard to success. What does that look like?

Jenny Wood: Well, we’ve all got those people in our life who we’re jealous of. It could be a friend, it could be a colleague. And I say use envy as your engine and steal their blueprint. So, there was someone named Molly who I just deeply admired. She was a peer of mine. We were always competing for promotions and I always thought she was three times as good as I was. But instead of being jealous and having it create a scarcity mindset for me, I thought of it as an abundance mindset where I could learn from her. I could get deeply nosy and I could kind of discover her recipe for X, Y, Z skills. So she was really good at project management. And anytime we were launching a new program, she would have this awesome Gantt chart, which had all of the dates and the accomplishments that needed to happen over a six-month period of time. She was really good at communicating next steps. She was really good at delegating. She would bold the person’s name in each email and put a deadline for what needed to happen next. She would thank everybody and be very positive and empathetic.

And so, rather than just be jealous and say, oh, why am I not good at Molly? Like I resent her. I just went to her and I said, Molly, could I do three 20-minute sessions with you where you review some of these project management skills with me and I can basically steal your blueprint? And I would write down these things on an index card and I would put them by my desk and I would use her strategies. Or I did this with another manager, Ted, who was just such a phenomenal presenter and never said, um, in his presentations. And so, then I would gamify it for myself and I’d say, I’m gonna count how many times Ted uses um, in a 10-minute presentation, and I’m gonna try to beat it. So again, rather than being jealous, I used envy as my engine and I would steal their blueprint. And that is rooted in being nosy. It’s being curious versus jealous.

Brett McKay: This reminded me of Plutarch, the famous Roman biographer, philosopher guy. He talks about two types of emotions. There’s envy, where you see someone who’s better than you and you just feel bad and you wanna bring them down. And then he says, “The opposite of that is zeal.” It’s where you admire someone’s excellence and then you wanna imitate it.

Jenny Wood: I love that.

Brett McKay: So curiosity, being nosy can lead to zeal instead of envy.

Jenny Wood: I love that.

Brett McKay: I really like that.

Jenny Wood: I love that.

Brett McKay: Let’s talk about being manipulative. You had an instance where you used manipulation on a past AOM guest, and that’s Vanessa Van Edwards. She talks about charisma. How did you manipulate Vanessa into helping you achieve one of your goals?

Jenny Wood: Yeah, well, I really wanted to meet Vanessa. We haven’t talked about obsessed, but I’m obsessed. I wanna meet the best people. I wanna do the best work. I wanna help people in the most high-impact way. And I knew that part of that was building those relationships with authors so that I could partner with them around time of book launch, and also just learn from each other and enjoy each other’s friendship and mutual value exchange. So I was headed to Austin for some work meetings. Someone had just introduced Vanessa and me over email. And so I said, I’m gonna be in Austin Thursday through Sunday. I would love to take you out for coffee. And she said, “Oh, what are the chances? I’m actually gonna be out of town those exact dates for a keynote.” And so, I think a lot of people would just take no for an answer and be like, okay, another time. And of course, another time never comes. But I wanted to capitalize on this opportunity. So I said, what time does your flight depart on Thursday?

And she said, “It departs at 3:00 PM. Well, my flight was scheduled to get in later than that. But a quick little switcheroo flight change and $60 to Delta Airlines had me coming in before her flight so I could meet her. And I said, what are the chances I get in at 1 O’clock? And so, what if we met right by your gate for coffee? So, did I lie? Yeah, sure. Liar, liar, pants on fire. But I will stand behind that lie all day long that I wasn’t actually originally getting in at 1:00 PM. And maybe I even said I was getting in at 1:00 to just make sure it worked for her before I made the flight change. So I think I actually did lie about the time my flight landed before I made the change. But I tell you, $60 to meet Vanessa Van Edwards in person, it’s a bargain at twice the price. And so, we feel like everything has to be coincidental or just has to work out or fate. But man, I just believe that serendipity isn’t found, it’s made. And manipulative reclaimed is the courage to build influence through empathy and to build lasting relationships.

Because whether you’re selling a product, an idea, or yourself, the ability to end friends, allies, and supporters is all about mutual benefit. So figure out what people want and go get it for them. In fact, something happened this morning where I got an email from the person who ran the PR campaign for the book. And she said, actually, I got an email a couple weeks ago, but I totally forgot to respond to this. It said, hey, would you be willing to write a testimonial for me on LinkedIn? So I would call that nosy, right? That’s great. And then I forgot to respond because I’ve had a lot going on. And then she followed up. I’d call this bossy. She said, “Hey, I hate to nudge you, but I’d really appreciate this review on LinkedIn. Any chance you could do that?” And so, what I think would have made it even more powerful, is if she’d been manipulative and said, “And by the way, I’ve drafted a couple sentences for you that you can tweak as you see fit.”

Because when I talk about manipulative and how it’s all about finding mutual benefit and figuring out what people want and getting it for them, what I want is time back. So I love doing favors for people, but they take time. And so, had she been manipulative and said, “I’ve already written it for you.” That gives me what I want, which is time back and makes it a lot easier for me to say yes. So I did say yes, but now I have to do the work. And it’s still something I have to add to my to-do list. So that’s where manipulative can be such a good thing and win-win and expand the pie, whether you’re changing your flight to meet somebody because relationships should be high reward, but also high investment, or asking someone to do a quick favor for you, like my PR person did today.

Brett McKay: Yeah, so being manipulative, it’s all about just being influential. That’s what it’s all about. And your definition of just being influential is like, thinking win-win, finding out how you can get what you want and need, and while at the same time delivering what someone else needs and wants. It reminds me of this famous quote from Dwight Eisenhower about leadership. And he said, “Leadership is the art of getting someone else to do something you want done, because he wants to do it.”

Jenny Wood: Oh my gosh, that’s so beautiful.

Brett McKay: Manipulative, but that’s just leadership. That’s being influential.

Jenny Wood: Yeah.

Brett McKay: Yeah. So last one, you talked about obsessed. You’re obsessed with meeting Vanessa Van Edwards. That’s another one of your traits of wild courage. What does positive obsession look like?

Jenny Wood: Well, it’s pushing, persisting, performing, because frankly, none of these traits will serve you if you don’t learn to deliver, not for some company, but to achieve your own ambitions. So obsessed for me was, I wanted a job at Google in 2006. I was bright-eyed and bushy-tailed and I submitted my application online having no clue what the job was that I submitted it for. But I discovered there was maybe sort of possibly a formatting funkiness when I uploaded my resume. And whether there was or wasn’t, when I didn’t hear back from Google, I used that as an opportunity to print out that resume on a piece of paper and hop in my mom’s 10-year-old Honda stick shift and drive to the Google office and sit there on the couch until someone came out and talked to me. And I remember the receptionist, it was a shared office space, was like, no, it’s not really protocol for Googlers to come out and talk to you. You can drop the resume here. And just like firm as a tree rooted to the ground, with my smile kind of like, cheeks quivering as I kept that smile on.

I was professionally persistent and said, oh, it’s okay, I’ll wait. I really do need to talk to somebody because there was a problem with my resume. There’s this study that says, people defer to because. It was a study about people standing in line to make Xerox copies and someone from the back went to the front and said, “I need to go to the front of the line because I need to make copies.” Just because they said the word because, they were more likely to be let into the line, even though of course, everyone was there to make copies. But the research suggests that people defer to the word because X, Y, Z. So I said, because there was a problem with my resume, I need to speak to someone. And eventually someone named Elizabeth came out, and I talked a little bit about how I had just come back from working abroad and backpacking through South America, which I understood were very googly skills or things that people did to be kind of well-rounded and global citizens. And then, then and only then, did I hear back from Google once I showed up.

Actually, not even then. I didn’t hear back. I didn’t get her business card. And then I tried every single permutation and combination of first initial, last name, first name, last name, just last name @google.com. Her name was Elizabeth Kelleher. So I emailed E. Kelleher, Elizabeth Kelleher, Liz Kelleher, Elizabeth@google.com. And then finally, I found the right combination. And when I followed up, then I heard back. So that is my flavor of obsessed. And it’s okay to be obsessed. It’s okay to stick your neck out. It’s okay to show that you want something deeply, because people like enthusiasm. People like energy, people like positivity. And that’s what I was trying to show, because it didn’t work just submitting my application online. Silly protocols and rules are there to deter the deterrable. But I just decided I was gonna be undeterred. And I got the job. And here we are almost 20 years later.

Brett McKay: Yeah. You got to play it hot. Don’t play it cool.

Jenny Wood: Yes. Definitely.

Brett McKay: So we’ve talked about these different traits. Is there one you think that people would get the most benefit from working on or like the one that people struggle with the most that if they started working on today, they’d see a lot of ROI? .

Jenny Wood: I think shameless. I think there’s just a lot of change in the world right now, a lot of economic uncertainty, a lot of change with, the onset of AI, a lot of layoffs, a lot of reorgs, and that’s hard. There’s this moment where my husband and I were living with my grandmother on her pullout couch in Manhattan while we were job hunting. And John shared some unfortunate news. We sat down to dinner. He said, “I’ve been part of a major company restructure and I got laid off today.” Well, I’m crushed as a newlywed, but I look across the table at Grandma Lila, who was like, a total spitfire at four foot 10 and 90 pounds. She was not just shameless. She was unstoppable. And she said, “John, no is just an opening offer. Don’t sign the paperwork.” And John and I look at each other trying to silently communicate what we’re thinking. And then finally, John sighs and says, uh, I think a layoff is like a one-sided thing, Grandma. They say, you don’t work here anymore. And I say, okay. And that’s when Grandma Lila sighs and says, “Well, sure, it would be more comfortable to take no for an answer, but don’t let fear shape your decision, don’t let shame shape your decision. You both want something, right? They wanna get stuff done, even though they can’t afford to pay you. And you want a job because it’s easier to get a job when you have a job.”

So finally, John relents. And the next day he goes to his VP and he half-heartedly offers to stay on for 10% time and pay, while he job hunts. And shockingly, they accept. Now, I’m not sharing this as some influence tactic per se. The point is Grandma Lila’s lesson. Don’t let fear, don’t let shame shape your decisions. Get shameless.

Brett McKay: Yeah, and it worked out for your husband, ’cause he got some time off. He had a little money to live on, kept his benefits. And then a few months later after this crisis that this company was going through, he kind of abated. The company hired him back full time. And it was all because he’s willing to do something we think of as a bad thing, to be shameless. He had to be uncomfortable and ask for something that apparently wasn’t an option. Well, Jenny, this has been a great conversation. Where can people go to learn more about you and your work?

Jenny Wood: Well, the book’s available anywhere. Electronic, e-book, audiobook, hardcover, Amazon, anywhere books are sold. And then you can find me on itsjennywood.com. And I love helping organizations with keynotes. I love helping execs through one-on-one coaching. I do some small group coaching. And I would love to be in touch and help you find your wild courage wherever you are and whatever you are chasing.

Brett McKay: Fantastic. Well, Jenny Wood, thanks for your time. It’s been a pleasure.

Jenny Wood: Thank you so much, Brett.

Brett McKay: My guest today was Jenny Wood. She’s the author of the book, “Wild Courage” It’s available on amazon.com and bookstores everywhere. You can find more information about her work at her website, itsjennywood.com. Also check out our show notes at aom.is/wildcourage, where you can find links to resources and we delve deeper into this topic.

Well, that wraps up another edition of the AOM Podcast. Make sure to check out our website at artofmanliness.com where you can find our podcast archives, as well as thousands of articles that we’ve written over the years about pretty much anything you can think of. And if you haven’t done so already, I’d appreciate it if you’d take one minute to give us a review on the podcast or Spotify. It helps out a lot. And if you’ve done that already, thank you. Please consider sharing the show with a friend or family member who you think would get something out of it. As always, thank you for the continued support. Until next time, it’s Brett McKay. Reminding you not just to listen to the AOM Podcast, but put what you’ve heard into action.

This article was originally published on The Art of Manliness.

The era of artificially intelligent large language models is upon us and isn’t going away. Rather, AI tools like ChatGPT are only going to get better and better and affect more and more areas of human life.

If you haven’t yet felt both amazed and unsettled by these technologies, you probably haven’t explored their true capabilities.

My guest today will explain why everyone should spend at least 10 hours experimenting with these chatbots, what it means to live in an age where AI can pass the bar exam, beat humans at complex tests, and even make us question our own creative abilities, what AI might mean for the future of work and education, and how to use these new tools to enhance rather than detract from your humanity.

Ethan Mollick is a professor at the Wharton business school and the author of Co-Intelligence: Living and Working with AI. Today on the show, Ethan explains the impact of the rise of AI and why we should learn to utilize tools like ChatGPT as a collaborator — a co-worker, co-teacher, co-researcher, and coach. He offers practical insights into harnessing AI to complement your own thinking, remove tedious tasks from your workday, and amplify your productivity. We’ll also explore how to craft effective prompts for large language models, maximize their potential, and thoughtfully navigate what may be the most profound technological shift of our lifetimes.

Connect With Ethan Mollick

This article was originally published on The Art of Manliness.

Think of all the texts, emails, and social media posts you’re inundated with each day. Sometimes you read them, and sometimes you swipe them away, telling yourself, perhaps not so honestly, that you’ll revisit them later.

If you’re the sender of such missives and memos or the creator of content, you hope the recipient has the first response, that, instead of deep-sixing your message, they take the time to engage and take action on it.

How do you increase the odds of that happening? Rather than just guessing at the answer, Todd Rogers has done empirical experiments to discover it. Todd is a behavioral scientist, a professor of public policy at the Harvard Kennedy School, and the author of Writing for Busy Readers: Communicate More Effectively in the Real World. Today on the show, Todd explains the four-stage process people use in deciding whether to engage with your writing, whether in a personal or business context, and how influencing these factors not only comes down to the style of your writing, but its overall design. Todd offers tips to improve both areas, so that you can effectively capture people’s attention.

Resources Related to the Podcast

• AoM Podcast #971: The 5 Factors for Crafting Simple (Read: Effective!) Messages
• AoM Podcast #666: The Power of Brevity in a Noisy World
• AoM Podcast #580: Why People Do (Or Don’t) Listen to You

Connect With Todd Rogers

• Todd on X
• Todd’s faculty page
• Writing for Busy Readers website

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Brett McKay: Brett McKay here, and welcome to another edition of The Art of Manliness podcast. Think of all the texts, emails, and social media posts you’re inundated with each day. Sometimes you read them and sometimes you swipe them away, telling yourself, perhaps not so honestly, that you’ll revisit them later. If you’re the sender of such missives and memos or the creator of content, you hope the recipient has the first response. That instead of deep six-ing your message, they take the time to engage and take action on it. How do you increase the odds of that happening? Rather than just guessing at the answer? Todd Rogers has done empirical experiments to discover it. Todd is a behavioral scientist, professor of public policy at the Harvard Kennedy School, and the author of Writing for Busy Readers, Communicate More Effectively in the Real World. Today on the show, Todd explains the four stage process people use in deciding whether to engage with your writing, whether in a personal or business context, and how influencing these factors not only comes down to the style of your writing, but its overall design. Todd offers tips to improve both areas so that you can effectively capture people’s attention. At the show’s over, check at our show notes at aom.is/busyreaders.

All right. Todd Rogers, welcome to the show.

Todd Rogers: Thanks for having me.

Brett McKay: So you are a professor of public policy and you recently co-authored a book about how to write for busy readers. What’s the connection between researching and writing about public policy and writing for harried people living in the TikTok age?

Todd Rogers: I’ve never been asked to actually defend why this is public policy. I guess it starts with I spent a decade working on how do we communicate to busy voters trying to mobilize voters to participate in elections, and then a decade working on how do we communicate with busy families from schools to get kids to go to school and kids to do better. And then five or six years before Jessica and I wrote this book, working with leaders across industries on how do we communicate to our employees, stakeholders, customers, constituents, and yeah, so I guess the common thread is across all these categories, across every domain of life, we are communicating to busy people. And if we wanna be effective at doing it, we have to understand that our readers are busy and we should write in a way that makes it easy for them.

Brett McKay: Yeah. With public policy, you’re trying to get people to do things, but in order for them to do the thing that you want them to do, you have to communicate that to them?

Todd Rogers: Yeah. I describe it as stage zero of every intervention we deliver. Is do we capture people’s attention long enough to deliver whatever we’re trying to communicate? So yeah. So if we are trying to have people sign up for a program or, you know, comply with the law or show up to court on a specific court date, we need to make sure we are communicating to them effectively.

Brett McKay: So you start off the book defining what effective communication is, what effective writing is, and you’ve developed this definition based on research as well as your own experience as a reader and writer. So what makes writing effective?

Todd Rogers: I think we probably start with the reader. So it’s funny, we talk about writing as if we are teaching writers, but the entire question of effectiveness is, do we succeed in communicating some thought from our head into the head of a reader? And so when we talk about this work, we’re like, okay, imagine you own a radical different take on writing. It’s not enough to have everything in there and then shift the responsibility to the reader. Imagine if it was always your fault if the reader did not read what you gave them. If it was always your fault, and so it’s your responsibility to make sure they read it and you don’t control their lives. All you control is what you put in front of them. Then just, it takes a whole new orientation. Effective writing is writing that we succeed in delivering the key content into someone else’s head at their leisure.

Brett McKay: And then at the beginning, I loved how you applied the things you write about in this book, in your book, and you lay out these sort of bullet points of what you found to be effective writing. Things like effective writing has a well-defined purpose. There’s a reason why you’re doing it, like, you know, and the reader can pick that up right away. It says, effective writing helps the writer as well as the reader. How does effective writing help the writer as well as the reader?

Todd Rogers: Writing often helps us clarify our own thinking, and I think we conflate that with the other use of writing, which is getting an idea from me to you. And they are two totally different functions. And often we write our first draft and then at the end it was clear what we think that the highest order goal is. But that’s actually stage one. Stage two is then we need to actually make it as easy for the reader as possible to get it. The way it makes it easier for the writer. Writing effectively helps writers because one, it helps us achieve our goals, which is Jessica and my objective with this book, helping writers be more effective in achieving their goals. But it also, and we’ve all experienced this, the haranguing and harassment of people who haven’t read or responded to what we sent them, ineffective writing becomes a huge burden on the writer because people aren’t showing up, people aren’t responding, people are asking you questions. So writing effectively helps writers because it saves us all the follow up and all the hassle that we are experiencing as a part of hassling other people to respond to us. It saves you from that irritation.

Brett McKay: Yeah. Another point you make, effective writing is not the same as beautiful writing. Flesh that out for us.

Todd Rogers: We are all taught how to write well. K through 12, K through college, we are taught these ideals of what good writing looks like, what beautiful sentences are, and using advanced vocabulary to be more precise. And I think that’s a critical stage on the road to becoming an effective person. But there’s a totally different project, which is not meeting some ideal, but actually communicating in the world to people who are not paid to read your writing and people who are most of the time trying to move on as quickly as possible. Like their goal is to hit delete or hit next as quickly as possible, often without even knowing what your point was. And so it’s like effective writing is writing for those people, not for people who are paid to give you feedback on your writing.

Brett McKay: Or it’s not for a novel for example. Like you might use some flowery language in a novel ’cause that’s what you’re trying to… You’re trying to do something. It’s basically beautiful writing and effective writing have two different goals.

Todd Rogers: Totally, yeah. A novel’s just a different function. We think of effective writing as being about professional practical writing where you’re texting a friend or you’re writing a web content or you’re writing an email to a coworker. All of it is like, it is not, you know, we’re not trying to layer in a third level of meaning with close reading about what adjective we used. We’re actually just trying to practically communicate something.

Brett McKay: Right. So effective writing is about getting stuff done, and you guys aren’t arguing in this book that we need to, you know, do sort of like an Orwellian news speak where all of our writing becomes effective writing. There’s still a place for New Yorker articles, there’s still a place for Tolstoy in writing like that. It’s just that you’re focused on how can we write so people get stuff done. That’s the focus.

Todd Rogers: Yeah, I like that. I mean, we probably could have incorporated that into the title. Yeah. There is a place for all that stuff, although that is a totally different function. It is leisure. You read the New Yorker Tolstoy because you are reading it recreationally to entertain yourself. And that is different than working your way through your text messages or your inbox.

Brett McKay: As a guy who’s on public policy, what have the consequences been of ineffective writing? Like real world consequences?

Todd Rogers: You could go across any domain for… It could be ineffective. Let’s say you’re a government and you’re communicating to the people who are delinquent in taxes, you’re mailing them and they’re not reading it. There’s all these studies on people are released from arrest and they’re given court summons. And if it is written in a way that is easy to read, they’re way more likely to actually show up to court and not have bench warrants issued for their arrest or signage in your public park asking you to pick up your dog’s poop written in pretty incomprehensible ways. Personally, like I have started two organizations. One is the Hub in Washington DC of using behavioral science and behavior change on public political communications and effective political communications, whether it’s Get Out the Vote or Fundraising or Volunteer Recruitment or Persuasion.

Another is a company that works with K12 school districts in communicating to families effectively, gets kids to go to school or not. And so writing in a way that makes it hard to understand, or just writing the way we sometimes do can undermine these important goals that organizations, campaigns, schools, companies have, which is trying to achieve some goal that is good for both the person who’s reading and the goal of the writer.

Brett McKay: Yeah. And I’m sure everyone’s seen examples of the bad consequences of ineffective writing at their own work. You know, the company sends out a memo trying to get you to do something, but it’s written in this convoluted way or there’s just too much going on in the memo that there’s hardly any compliance at all.

Todd Rogers: Yeah. There’s, I mean, there’s some great examples. So there’s like a sign, there is a center for plain language. It is an organization that gives an award every year called the WTF Award for just the worst signage that has been created that year. WTF means words that failed, obviously, and the sign, a real sign, getting people to pick up their dog’s poop was persons shall remove all excrement from pets. I am certain that that was an ineffective sign and that 90% of people didn’t read it and understand that the goal was to scoop your pet’s poop. So yeah, it’s comically bad, but it’s clear. I mean, I’m sure the lawyers understood it.

Brett McKay: Yeah. So before you start writing, the thing you say we need to do first is get inside your reader’s head. What do people need to understand about readers today so they understand like how a reader decides whether or not they’re gonna read something, whether they’re gonna read it all the way through, et cetera.

Todd Rogers: I think the TLDR of the whole thing, the too long didn’t read of the whole book or of this entire project that we’re doing is everyone is skimming everything, right? No one is spending as much time reading as we are writing and thinking about it. And so we need to write in a way that accommodates the reality that everyone’s skimming. So you get inside their head and know that they’re super busy and they have a long list of things to do and a lot of things they’d rather do than read whatever you’re sending them. And that includes text messages. We’ve run these experiments where even text messages, writing them so they’re easier to read makes people more likely to understand and respond to them. So if you’re gonna get in the reader’s head, it all starts with everyone’s busy and everyone’s skimming. And rarely do people care as much about what we’re writing as we do.

Brett McKay: And I love this too. You lay out a four stage process that readers go through when they’re deciding whether they’re going to engage with a piece of text, and this is whether it’s an email, a text, a Slack message, a social media post. The first part is you have to decide whether you’re gonna engage with it at all. So you just look at the thing and you kind of skim it and you’re like, well, am I even going to dig deeper into this? Second is, if you decide to engage, you must decide when to engage. Like what does that mean? Like sometimes you don’t read it right away?

Todd Rogers: Yeah, it’s a combination of the first and second. The second and third, which is the first most is the… I think the most important and kind of the most subtle, but everyone will relate to, which is if you have a long thing in front of you and a short thing in front of you, which are you gonna do first? Almost everyone is gonna do the short easy thing first. And so you look at it, it’s a wall of words and we call that deterrence. You are just deterred from reading it at all. And that’s like, I think that everyone should relate to. You open something, even a text message like, I can’t deal with that right now. Or you go to a webpage and it’s a long wall of words. The second and third are basically like, okay, so do I engage with it now or later?

And whenever I engage with it, how deeply do I read it? And I assume we actually have lots of evidence. What happens is the more difficult it is to read, the more you just sort of dart around, bounce around, see if you get the gist and eventually give up and move on. So those are the one through three. And the fourth one is deciding whether to respond or not, if you’re asking for some kind of response. And the easier the response, the more likely people are to do it. Just like the shorter the message, someone’s more likely to read that than a long one. If it looks like it’s gonna require a lot of research or it’s unclear what the question is, all these things make it just less likely people will deal with it at all, but definitely less likely they’ll deal with it now.

Brett McKay: Okay. So let’s talk about what we can do as writers to increase the odds that someone will want to engage with whatever we’re throwing at them. They’ll want to maybe act on it faster, sooner rather than later. And, you know, engage with all of it and as well as, you know, respond, get more of response so we can get stuff done. And you and your co-author lay out six principles that writers can use to make sure that their writing is effective. The first principle, and you just kind of referred to it just a minute ago, less is more. So how does more often get in the way of your readers engaging with your text?

Todd Rogers: This is my favorite. I don’t wanna speak for Jessica on this. I love this. Less is more. You could probably go back to there’s a quote that every clever person who’s ever been alive has been credited with this quote, which is, I would’ve written you a shorter letter if I’d had more time. And what I love about that is it is worthy of apology. I have wronged you by giving you this longer than it needed to be text. And second, it takes more time to write less. Both of those are sort of central to this less is more idea. And the idea is, and we’ve run randomized experiments, lots of them, where the more sentences you add, the more ideas you add, just the longer it is, the less likely people are to read and understand and respond. Whether it’s soliciting a response, getting people to fill out a survey, getting people to… We worked with the, I don’t know if we named the party, but one of the big political parties, Democrat or Republican on a big fundraising email with 700,000 donors and arbitrarily deleted every other sentence.

So it didn’t even make sense anymore. So we cut it in half by making it incoherent and still increased donations. We’ve done lots of versions of this, but the idea is just you need to know there’s a trade off. The more you add, the less likely someone is to read, understand, and respond. And the optimal length in content is not nothing or one sentence. It’s just a trade off. You just need to know, the more you add, the less effective it’ll be. But you gotta make those trade-offs.

Brett McKay: Yeah. So you lay out some rules to apply this less is more. First one, use fewer words. And I mean, if you went to college or even high school, they taught, you know, this whole elements of style, just eliminate, and that was one of the rules. Eliminate needless words. You know, have everyone seen these wordy phrases for the reason that instead of saying that, just say, because you know.

Todd Rogers: Right. In order to.

Brett McKay: Yeah.

Todd Rogers: Just say to.

Brett McKay: Just to. Whether or not, well, just weather.

Todd Rogers: Yeah, exactly.

Brett McKay: Personal opinion. Well, there’s only one type of opinion. I mean, so just things like that can go a long way. But I love this idea. Rule number two, to include fewer ideas. So we’re talking about, maybe it’s a memo or an email you’re trying to write. Oftentimes you wanna try to cram as many things as you can in that piece of text. But what your research shows is like the fewer, the better. The fewer ideas you have in your email or memo, the more likely people are going to read what you wrote.

Todd Rogers: Yeah. And that’s hard. I mean, it’s hard for people because it requires judgment and prioritizing. Like what’s the most important thing I’m saying here? And it would be good for you to know this, but it’s not necessary. And so there’s trade offs all the way, like there are workarounds, like if it’s a webpage, you could have a link to the more content, or if it’s an email, you could have it below the sign off or as an attachment. Or if it’s a report, it could be an appendix. You can keep the detail, but you just need the core thing to be the core thing. And what we have is all this experimental evidence showing that when you dilute it with more content, you just are less likely to achieve your goal. And it just requires judgements and trade-offs the whole way.

Brett McKay: Yeah. You gave this great example. This was like a text. Could be a text to get together with some friends for dinner. The original one is, I’m looking forward to our 6:30 dinner tonight. Let’s eat at Tina’s Italian restaurant at 651 Ocean Drive. Their breadsticks are awesome. I haven’t had their lasagna, but I’m ready. It’s supposed to be tasty. Let’s meet at my place 15 minutes early and we’ll walk from there. Sam and Joy, are gonna join us for dinner too. Man, if I got that text, I’d be like, oh, geez, I’m gonna just have to look at this later. But you know, you could have just said, Hey, we’re having dinner, it’s at 6:15, meet at my place. That’s all you needed.

Todd Rogers: Right. And there is information in the rest of it. It’s just you got… And if you’re aware that there’s a trade off, then you have to treat it differently. Since writing the book, I’ve worked with a guy who’s in the CIA on who writes intelligence assessments in this group, in this intelligence group, and there’s 70 pages and that’s the norm. And he was like, well, how do I write less? Because if I write 35 pages, they’re gonna think I didn’t do my job. ‘Cause the norm is the norm. The norm is 70 pages. And so I actually love that because the answer is you can’t. Like, you have to write for your audience and what your audience expects, it has to look like what your audience expects. I mean, Jessica and I wrote a 207 page book where one of the principles is write less. The book, expect the book to look like a book. And so you have an audience that has norms and expectations, it has to look like what they expect, but then within those constraints, the easier you make it for them, the better. And so with a text message, I don’t think anyone cares whether you are interested in the breadsticks or not. They’re just like, when do I show up and who’s gonna be there?

Brett McKay: Right. Okay. Let’s move on to the second principle. Make reading easy. How do we typically make reading more difficult for our audience?

Todd Rogers: We write in grammatically correct, complicated ways. And so whether it is a long sentence or using unfamiliar, uncommon words, or writing in a like grammatically complicated way, it just makes it more cognitively taxing. So like a different way of thinking about all this in length and also writing style is just how do you make it less cognitively effortful? The easier it is, the more likely people will be to do it. So even if they’re gonna work their way through it, it’s just unkind to write in a way that taxes them and burdens them. We ran one experiment with Vice President Harris when she was the Attorney General of California, where, and I mean, I don’t know, the listeners are not, I hope no one is writing like this, but the California State Legislature required that schools send families letters when their kids are late or absent. And it starts with California Education Code, section 48260 provides that a pupil, child, subject to compulsory, I mean, it’s not even written for humans, and it’s like being sent to hundreds of thousands of families so the idea is we just add a round of editing where we just ask how do I make it just easier to pull the key info out? Even if we are correct, complete, and grammatically accurate, we just make it easier.

Brett McKay: Yeah, so you apply some rules. Use shorten common words, so there’s that whole quote. I think it was Mark Twain. Don’t use a $5 word when a 50-cent word will do. So instead of saying acquiesce, you can just say agree. You know, you don’t have to get fancy. You can save the $50 words for your New Yorker article you’re writing for yourself.

Todd Rogers: Yeah, for yourself, exactly.

Brett McKay: Yeah, rule two, just use straightforward sentences. So this is, you’re not gonna do clauses and using semicolons and et cetera. Like, just really straightforward. Like, you can just glance at it, you know exactly what it says. Yeah, and then rule three, write shorter sentences. So, you know, just gotta edit, edit, edit, edit until you can get it down. You start writing like Hemingway, basically.

Todd Rogers: Yeah, that’s the idea, but no simpler than it needs to be. Right, like as simple as it can be, but no simpler.

Brett McKay: Yeah, so you give an example of a hard to read complex sentence and then editing it so it’s easier to read. Here’s the hard to read version. Often crafted from insidiously complicated language designed to abstract contentious details, ballot measures are propagated as a tool of direct democracy in 24 states in Washington, DC. So yeah, grammatically correct, but that was hard to read. Here’s the edited version. Ballot measures are used as a tool of direct democracy in 24 states and Washington, DC. They’re often written with deceptively complex language designed to hide controversial details. So yeah, that was a lot easier to read. We’re gonna take a quick break for a word from our sponsors. And now back to the show. Okay, second principle again, make reading easy. So we’re just gonna use fewer words, write shorter sentences and make sure your sentences aren’t hard to read with those parentheticals and semicolons and references back to things you said in a previous clause. Third principle is design for easy navigation.

Now, I’m sure a lot of people are listening to this. They probably learned in high school or in college, you know, some ideas or some rules about being concise with your writing. We’ve all probably read elements of style and that’s one of the rules. But I don’t remember being taught this. Well, actually I was taught this in law school, but I wasn’t taught this in undergrad or high school is thinking about the design of your writing so that it’s easy to read. So what does that look like? How can we lay out our writing so that it’s easier to navigate?

Todd Rogers: Yeah, I like this one. This is, I like all of them equally, but I like this and less is more the most. But the idea is it’s not even about writing, but realizing that people are gonna look at it and decide, do I read or not? Remember that stage of deterrence. Or once they’re reading, they’re just gonna dart around and see if they can get something out of it before they give up. And one metaphor or at least framework we use for thinking about it is that people may allocate like a fixed budget of time to reading your thing. And so then the question is just how do you make it easier for them to get what you want them to get out of it in that budget? And so that could be like adding headings. So it’s easy to know the structure. And when we actually do eye tracking, you see people jump around and read the headings first when they’re moving fast. Sometimes they just go first line, second line, but that’s when they’re anticipating reading the whole thing. But often they’ll just dart around and figure out what’s in here.

And we’ve actually run experiments where when you add headings in newsletters, you double the likelihood that people will read past the second paragraph and use anything in it past the second paragraph. The other one that people really like, and I really like, and I don’t know if you’re a veteran or how many of your listeners are veterans, but I work with a lot of active duty people in different branches of the military. One thing that they have in the US, started in the US Army and it spread across the militaries around the world is a thing called BLUF, bottom line up front, B-L-U-F, BLUF, bottom line up front. And it is a rule in the US Army, a rule that anything written to anybody, the first line has to be the bottom line. So there’s no long introduction, an enlisted person writing to a general, bottom line is the first line. And it makes it so much easier for readers and writers to know where’s the key info, where do I put the key info, where do I find the key info? But it especially helps people who are lower status, like an enlisted person writing to a general might have to say in the absence of that rule, like we ran into each other in Kandahar, you may not remember me, we chatted in the mess, I went to rival high school, we laughed about how the Philadelphia Eagles are gonna win the SuperBowl this year.

But I wanna ask you for a meeting. And so instead of the whole throat clearing, which would decrease the likelihood we get read at all, now they have this rule that doesn’t work everywhere, but having this rule in that environment and with that organization makes it just easier for everybody. And so another way to design for navigation is to have this kind of structure. So it’s easy to pull the key info out and jump around, but also when possible, make the bottom line super easy to pull out.

Brett McKay: Okay, so yeah, when you write an email, for example, just right at the very top, don’t you have to do the throat clearing stuff, just like here’s what this email is about.

Todd Rogers: Maybe, but it doesn’t work every, like it just depends on the expectations and norms, ’cause that can come off as too aggressive. I don’t do that. I still have a hope you’re well or good talking to you the other day. And I usually add that back. Like I’ll write my like all business part and then I’ll add some humanity to it because I don’t wanna come off as too aggressive. And so, but like within organizations, when we talk like the next step that Jessica and I are thinking and working on is like, so okay, so you’ve become more effective as a communicator. How do we get your team to be more effective? And it starts with just being intentional and explicit. Let’s just have a conversation. How do we write so we can all be on the same page instead of just letting these norms evolve without intention or guidance? Let’s be intentional about it. How do we write? Like the US Army decided BLUF so we can all be on the same page.

Brett McKay: Okay, I really like using headings. Like that’s something I learned in law school. When you write a memo, you break things up in headings so that the partner that you wrote the memo for can just glance at it and get to the information they might be particularly interested in. Another thing for easy navigation, add bullet points. Like using bullet points can help out a lot, especially if you’ve got more than two ideas or two requests in your communication.

Todd Rogers: Yeah, there’s a subtle one on the bullet points too where, which I think you were pointing to, is that if the bullet is kind of long, a skimmer still has to read the bullet to figure out what it’s about. And so one of the things that we have found is putting a title to the bullet, which may seem counter to fewer words. We’re just saying add a three-word title, which is extra words, makes it easier for a skimmer to know whether they should bother engaging with this bullet or whether they are free to move on. And so it’s a subtle thing, but the goal is just making it as easy for your reader to move on and get the key info that you want them to get. And then when we start talking about design, you can see that you want it to be aesthetically good-looking and consistent. And so you want the headings and titles to always look the same and things like that.

Brett McKay: Yeah, another rule you can apply for easy navigation, order your ideas by priority. That’s kind of that BLUF thing, maybe. But if you have more than one idea, like put the stuff that you care about the most right at the top, because the person’s gonna read that far and then they’re gonna start jumping around a lot after that point.

Todd Rogers: Yeah, yeah, exactly. And if they are gonna jump around, you wanna make it easy for them to jump around, which is why, like you said, you like to space it out with bullets or things, just making it visually easier.

Brett McKay: And then another rule, consider using visuals. Like don’t be afraid to put pictures in your communication. If that picture or visual can convey the message, what you’re trying to convey more efficiently.

Todd Rogers: Yeah, a colleague of mine and friend and mentor, Nancy Gibbs used to be the editor of Time Magazine. And I was really surprised to hear her say that a common feedback she would give to her reporters was does this have to be words? And I like, ’cause she’s a word person. And she said that that was a common challenge for writers, is like, is there an easier way to show this? Like, can it be a diagram instead of a full paragraph or two?

Brett McKay: And so the thing about designing for easy navigation, that takes time on your part as the writer. So it’s easy just to just crank out just a big block of text, maybe put a few paragraphs here and there. But thinking about headings, thinking about what could be bolded, thinking about the BLUF, that’s gonna take a bit more time than just cranking that thing out in just one fell swoop. You have to really be thoughtful about this. But the payoff is in the end. You invest that time upfront, so you save yourself some time and frustration on the back end.

Todd Rogers: Right, and if it’s really important for you, you wanna make it easy for the reader because you will be more effective. It’s also this kindness that I also think it’s kind of a subtle implication of all of it, is that it’s just nicer to your reader to make it easy in that way.

Brett McKay: All right, so the fourth principle is use enough formatting but no more. So I think one thing people do to help ensure that certain ideas stand out, they’ll use things like bold or underlines or all caps in a text message. How do people mess up formatting though when they’re trying to get their points across to the reader?

Todd Rogers: This has been the bigger surprise of writing this book for me. The biggest surprise has been people being really excited because they say, this has been a fight my entire career. And I have been saying, we need to write in a way that makes it easier. And people are like, this is just your taste and just your preference and has been dismissed. And now we bring to it all these randomized experiments and a lot of evidence from different ways of research. And it’s now actually a question of like scientific effectiveness. The other surprise has been when people email me, one, there’s a lot of anxiety I think that I’m gonna be judgmental and anyone who’s gonna email me, you do not have to worry. It turns out writing, reading and communicating are all hard. But the second thing is when I started saying use enough highlighting, but no more, it leads to people using different font colors, underline, bold, highlight, italics, all in the same thing. It was only eight sentences and there are six different kinds of stylistic formatting variants in the message. And the irony is that that actually is worse than nothing because it makes it harder for the reader to figure out what you think as the writer is the most important thing. Because if you only format, let’s say you bold one sentence, it is unambiguous to the reader. The writer thinks this is really important.

But if you do lots of different things, the six of the eight sentences, I have no idea as a reader what you think is most important and what any of the formatting even means. So use enough formatting. In surveys and experiments, we’ve seen that people jump to bold, underline and highlighted text. They jump to that and they think the writer is saying to them this is the most important content, get this. So it’s incredibly effective. It also licenses readers to not read anything else because they’ve gotten the key info and everyone’s goal is to move on. So you’ve got to use it carefully because it gets people to read that and also crowds out reading anything else. But then we use lots of kinds of formatting. It just confuses readers about what any of it means.

Brett McKay: Okay, so bolding, underlining, highlighting, it’s effective in getting the reader to think here’s what the writer thinks is important and to put their focus on that if that’s what you wanna do. And you see that a lot in online writing. Any formatting things that you see in online writing that aren’t effective?

Todd Rogers: I don’t like how links all get font color change and underlined because you actually, there is eye tracking research showing that people jump to that. And often the link is not the key info. The link is just the link. And so there’s this tension, there’s this norm. Everyone knows that’s what a link is, but it also kind of undermines the speed of consuming whatever we’re writing for people. And so actually the trade-off for me on that is like we wanna minimize the number of words that are linked if you can while still accurately describing whatever the link is. That’s sort of a small point, but one that aesthetically I don’t think we have a good solution to yet.

Brett McKay: All right, so use formatting, but don’t go crazy with it. You don’t have to use all the formatting options. Just pick one or two and then stick with that. And again, it’s gonna, the formatting use is gonna vary by context. Maybe in your organization you have a rule or a norm that you use in regards to formatting in order to show that this is important. So just follow that. The fifth principle is tell readers why they should care. But this is all about making sure that the reader actually engages with your content. So what can we do to show the reader like you should care about this and engage with this more than just a cursory glance?

Todd Rogers: Yeah, the way we thought about this is the obvious way to get a reader to read something is to write about something they care about. But we take it as given. The writer has the thing they wanna write about and the thing they’re trying to communicate. And it doesn’t really matter from the writer’s objectives whether this is the most interesting thing in the world for the reader, right? So we take as a given, you have your goal, your goal as a writer. Within that set of ideas or content, all we’re saying is you may as well emphasize the part of the things you’re going to say that they may value the most. So we report this experiment with Rock the Vote, which is like a voter registration organization that tries to target young people. And they were sending an email out to potential volunteers saying, will you volunteer to work at concerts to register concert goers to vote? And in one condition, the subject line was volunteer with Rock the Vote. And in the other condition, it was attend concerts for free. Maybe it was like volunteer and attend concerts for free. And so the subject line there is like drawing attention. The content is the same, exactly the same. You’re gonna volunteer at a concert and you’re gonna register voters. But we may as well emphasize the thing that people will value out of that set.

And so they ended up four X more effective, four times more effective, by just making the subject line focus within the set of ideas they’re gonna say in the message on the thing they think the recipient might care the most about. So that principle is just emphasize what the reader might care about within the bounds of what you’re already gonna say. We’re not saying you need to say something different. We’re just saying you may as well focus on the thing they may care about.

Brett McKay: Yeah, and then put that up front. Like don’t bury the lead on that. Don’t wait till the very end. Say, hey, this is why, you know, start off this like in the subject line. Here’s why you should care about this. And then put all the other information after that. And then another rule that you have for that for tell the readers why they should care is emphasize which readers should care. This is important ’cause sometimes you send out a message and it’s only going to a certain segment of the population. And if you make it too broad, you might end up causing the group of people you’re trying to communicate to just to ignore it completely.

Todd Rogers: Yeah, at minimum, it’s kind to your reader to let them loose. This is not for you, you’re free to go. But also in the intermediate term, as you communicate more, if you let people go when it’s not relevant to them, they’re gonna be more likely to attend when it is relevant to them.

Brett McKay: Yeah, you gave the example, like let’s say you have a grocery store and there’s been a recall on a product for safety. You know, the grocery store might put up a sign, notice important product safety recall information. Well, you know, if someone sees that and it’s like, well, I don’t know, maybe is it the product that I bought? I don’t, who knows, maybe I’ll just ignore this. And then you said, if you wanna have a reader’s perspective, the top line of that notice should say, if you bought soup XYZ in June, it has been recalled. And so like, oh, immediately the person seeing that, it’s like, well, did I buy that soup in June or not? And then they can make that decision whether they need to engage with it or not.

Todd Rogers: Right, well, Brett, also, I applaud you for getting, these are deep tracks in the book. You read it closely.

Brett McKay: I read the book.

Todd Rogers: Nice, yeah.

Brett McKay: And you make it easy to read. So it made me wanna keep reading it.

Todd Rogers: Yeah, we wrote it so it was skimmable. For anyone listening, it is easy to skim. But if you want the details on any topic, you can dive deep in it.

Brett McKay: You can dive deep. So the sixth principle is make responding easy. Not all communications require response, but a lot of the communications that we put out there to get stuff done, they require responses. So what can we do to make responding easier?

Todd Rogers: I know that there are other, that your listeners and you follow other behavioral scientists, like behavioral economists or social psychologists who work on behavior change, which is basically what my research has been on for the last 25 years. And all of that is this, which is the takeaway is, if you want someone to do something, we should make it easy for them. And so whether that means reducing the number of steps required to take the action or providing checklists or pre-populating forms, or even like, here’s something completely basic that we’ve all had, which is let’s schedule a meeting. There are four of us on an email thread. These six times work for me, which worked for you? And then if you reply in a paragraph, well, I can do the first time, but I’d have to move a couple meetings. The second time’s better for me, but the third doesn’t work. And the fourth could work if nothing else works. Like the amount of effort required to decipher which of the times you’re proposing actually work is, you know, you’re adding 35, 40 seconds to the next person to figure it out. If we actually wanted everyone to respond, you say, of those times…

These two work for me.

Brett McKay: Period.

Todd Rogers: Nobody cares whether it means you have to move a meeting. So the idea is if it’s important to you that someone get back to you you wanna make it as easy as possible. If it’s important for us we wanna make it easy for them. I’ll often ask students imagine you have a task that will take five minutes and a task that will take 30 seconds. Both of them are on your to-do list and you plan to do both eventually. Which are you gonna do first. Almost everybody’s gonna do the 30-second task first. And so the idea is you just wanna make it easy. As easy as possible.

Brett McKay: Right. And so that means maybe you have to do some decision structuring for the person. Like here I need you to make this decision. Just this one decision. And then after that you can maybe follow up if you need to make other decisions but just pick one thing you want them to respond to.

Todd Rogers: Yeah. In the less is more there’s fewer requests. If you ask someone to do two things you are less likely to get them to do any one of them than if you ask them to do just one. The idea is we’ve got to prioritize. We have our goals and we need to write in a way that makes it easy for the reader to help us achieve our goals. And that means simplifying the request. Like you’re saying if I asked you what do you think versus I’m going to submit this. Agree or disagree? Yes or no? Do you sign off? They end up being… It’s much easier to say yes agree submit than an open-ended what do I think? And so it’s just my prediction and some of the evidence is… All the evidence is consistent with. People are more likely to respond and more likely to respond sooner when it’s a yes no question than open-ended.

Brett McKay: Yeah. Another rule you have in this make responding easy is organizing key information that’s needed to take action. So let’s say you make a request for something at your work or something but then in order for the reader to answer that they have to start trolling through all this information or kind of doing this scavenger hunt to even start putting together a response. Well, if that’s the case they’re gonna drag their feet on that or they’re gonna take a long time. Instead if there’s an answer you need right away provide the reader with as much information as possible that they need in that communication so they can give you the response you need. Okay. So those are the six principles and I think if people had those in mind as they wrote they’d get a lot more done with their writing. At the end of the book beyond these six principles you talk about some other ideas that you’ve seen in your research and your own personal experience when it comes to communicating and getting people to respond to your writing and getting stuff done with writing. And one topic you talk about is frequency of communicating.

This is something I struggle with when it comes to communication in my business or in organizations that I belong to ’cause I worry about communicating too much. ‘Cause I don’t wanna bug people. But something I’ve noticed is that when I do communicate more I get more responses. I get more people showing up for things or doing things. So what’s the research say? How often should I hit people with the same information so that it’s effective?

Todd Rogers: There is not a single answer for this just like there’s not a single stable answer for when should you communicate because the equilibrium changes. If the answer is Thursday at 3:00 PM everyone is gonna communicate on Thursday at 3:00 PM making yours less effective and then the equilibrium moves around it’s an unstable equilibrium. Similarly for frequency of communication I think there isn’t a good answer but my first pass at it is if you think that your reader wants your communication and values it like your newsletter? If you think that they really want it then you wanna be consistent so they know when to expect it and have it look the same so they can recognize quickly what it is. In the intermediate term if we communicate all the time we will decrease people’s likelihood that they associate us with something they should read and they will start to view us as a pest and they will unsubscribe. And so I know there are a lot of organizations that have big lists. The balance that we’re always talking about is you can increase donation for example by sending more messages you also increase unsubscribes and so what’s the two, three-year horizon consequence is you may end up being worse off for having gotten more donations in this week by sending more messages.

But in the intermediate horizon you’re worse off. There isn’t a great answer. I don’t know. Do you have thoughts on this? It sounds like you wrestle with it.

Brett McKay: I wrestle with it. No. So it sounds like it’s the killing the goose that lays the golden egg problem.

Todd Rogers: Right. Yeah exactly.

Brett McKay: Right. You can extract a lot of value by doing a lot of frequency in the short term but in the long term you end up killing the thing that provides you value. So when it comes to let’s say you belong to I don’t know a sports league or I don’t know a church congregation there’s an event coming up. That’s the thing where I’ve found that more frequent communication helps up to a point. You can’t just do one and expect to get a response ’cause people might just miss that first email or they read it and then they forgot about it and then the event comes up two weeks later and they’re like I didn’t know about it. It’s like well I sent you that email. So I think something like that I need one email maybe two weeks out and then maybe a week out you send a reminder and then two days before you send a final reminder that could work. I mean, if you did a reminder every single day people are just gonna tune you out.

Todd Rogers: I think there’s consistency in that too Brett where it’s like I’m on a board where they send materials out a week in advance and then they send them the night before again. And so I know two weeks in advance I don’t need to deal with this ’cause I know it’s coming back right before. And so if they stopped doing that and they just did it occasionally I think I and the other members would all be less prepared because we’ve come to expect that oh this is just the forewarning before the real one. I think consistency is probably key there. People start to associate you with that pattern.

Brett McKay: Yeah. But I also think yeah frequency can be a tool to help a harried reader because people are just getting inundated with stuff and they’re gonna miss things. This can even happen with your friends with text messages, right? You send a friend a text and you don’t hear back from them and you think oh man they hate me. They don’t like me anymore. So now they… If their text inbox is anything like yours it’s just getting inundated with two-factor authentications, reminders about their kid’s doctor’s appointment. So maybe the friendly thing to do would be, Hey, follow up two days later if they haven’t gotten back to you because they needed that. So I think with frequency yeah there’s a balance but I think maybe don’t be afraid of nudging more than you think ’cause you’re probably not actually nudging ’cause the people probably didn’t see your initial message anyways.

Todd Rogers: Yeah, I like that. I also think when you talk about a friend or a coworker with whom you communicate a lot I do think the answer, and this is probably the answer for most questions is to communicate better and to actually have a discussion about it. And this is something that we stumbled into. Well, there isn’t a universal rule for this. Some people will view you pinging them again as like yeah man I read it. I got you. Stop harassing me. Others will be like Thank you. And so a different way if this is someone you communicate with a lot is to just ask. Would it be useful if I send follow-ups or not? I actually have all sorts of people that they have incredibly varied preferences and for people I communicate with a lot. I actually have started to learn what they are because I ask.

Brett McKay: I’m curious are there any AI tools that you’re seeing out there that are helping writers write more effectively?

Todd Rogers: Are you setting me up for… Did I show you mine?

Brett McKay: No.

Todd Rogers: Or is that…

Brett McKay: No.

Todd Rogers: So early on we trained GPT-4 or GPT-3.5 and then now GPT-4o the OpenAI’s latest LLM on the… With your listeners in the show notes I hope we’ll share the checklist. There’s a one-page checklist for how to write for busy readers and we trained the large language model on these principles and then we fed it what’s called Few-Shot Learning just three pre-post examples of emails an original and an edited. Original edited original edited. It’s incredible at editing emails so that they are skimmable and it now has hundreds of thousands of uses and I get emails all the time from people saying that they put any important message through it to just get suggestions. So it’s on our website. I’ll share it with you. It’s writingforbusyreaders.com but it’s very cool. The large language models you could think of as they learn inductively they consume all the way we’ve ever written and then they infer rules and predictions.

This is much more deductive top down. We’re like look there are these six principles. We should edit through the lens of these principles because this is actually what the science suggests people are more likely to read and respond to and it learns those and then it can revise in accordance with and we shouldn’t use words like in accordance. We shouldn’t use… It writes in ways that are consistent with that. So writingforbusyreaders.com but I love it. We’re trying to get it internalized by the other big large language model especially the ones who work in email clients.

Brett McKay: Well, Todd this has been a great conversation. Where can people go to learn more about the book? So I guess that one website?

Todd Rogers: Writingforbusyreaders.com writingforbusyreaders.com and the Too long didn’t read of this whole thing. If you made it to the end and you don’t know the big takeaway. The big takeaway is we should add a round of editing to everything we write where we ask ourselves how do I make it easier for the reader? How do I make it easier for the reader? Because the easier it is for the reader the more effective we are at achieving our goals and it’s just kinder.

Brett McKay: I love it. Well Todd Rogers thanks for your time. It’s been a pleasure.

Todd Rogers: Thanks Brett.

Brett McKay: My guest today’s Todd Rogers. He’s the author of the book Writing for Busy Readers. It’s available on amazon.com and bookstores everywhere. You can find more information about the book at the website writingforbusyreaders.com. Also check out our show notes at aom.is/busyreaders where you can find links to resources and we delve deeper into this topic.

Well, that wraps up another edition of the AOM Podcast. Make sure to check out our website at artofmanliness.com where you can find our podcast archives as well as thousands of articles that we’ve written over the years about pretty much anything you’d think of. And if you haven’t done so already I’d appreciate it if you’d take one minute to give us a review on Apple Podcast or Spotify, it helps out a lot. And if you’ve done that already. Thank you. Please consider sharing the show with a friend or family member who you think would get something out of it. As always. Thank you for the continued support. Until next time this is Brett McKay reminding you to not only to listen to AOM Podcast but put what you’ve heard into action.

This article was originally published on The Art of Manliness.

As you get older, you can start to feel like you’ll never achieve your dream or receive recognition for your contributions to a field, or that your best work is behind you.

Mo Rocca has compiled stories that demonstrate that you shouldn’t give up hope, and that no matter your age, the best may yet be to come.

Mo is a humorist, journalist, and the co-author of Roctogenarians: Late in Life Debuts, Comebacks, and Triumphs. Today on the show, Mo shares the stories and lessons of entrepreneurs, artists, actors, and more who achieved greatness or adulation in their twilight years or had a new spurt of creativity when they thought the well had run dry, including KFC founder Colonel Sanders, the artist Matisse, a couple of guys who didn’t receive their first war wounds until they were old enough to qualify for the senior citizen discount at Denny’s, and even a virile 90-year-old tortoise.

Resources Related to the Podcast

• AoM Podcast #849: Live Life in Crescendo
• Samuel Whittemore
• John L. Burns
• Frank Lloyd Wright’s Fallingwater
• Frank Lloyd Wright’s Guggenheim Museum
• Henri Matisse’s The Swimming Pool
• Documentary about Tyrus Wong
• Mr. Pickles the Tortoise

Connect With Mo Rocca

• Mo on X

Listen to the Podcast! (And don’t forget to leave us a review!)

Listen to the episode on a separate page.

Download this episode.

Subscribe to the podcast in the media player of your choice.

Read the Transcript

Brett McKay: Brett McKay here and welcome to another edition of the Art of Manliness podcast. As you get older, you can start to feel like you’ll never achieve your dream or receive recognition for your contributions to a field or that your best work is behind you. Mo Rocca has compiled stories that demonstrate that you shouldn’t give up hope and that no matter your age, the best may yet be to come. Mo is a humorist, journalist, and the co-author of Roctogenarians, late in life debuts, comebacks, and triumphs. Today in the show, Mo shares the stories and lessons of entrepreneurs, artists, actors, and more who achieved greatness or adulation in their twilight years or had a new spurt of creativity when they thought the well had run dry, including KFC founder, Colonel Sanders, the artist Matisse, a couple of guys who didn’t receive their first war wounds until they were old enough to qualify for the senior citizen discount at Denny’s, and even a virile 90-year-old tortoise. After the show’s over, check out our show notes at aom.is/lateinlife. All right, Mo Rocca, welcome to the show.

Mo Rocca: Thank you for having me, Brett.

Brett McKay: So you got a new book out called Roctogenarians, Late in Life Debuts, comebacks, and Triumphs. So you’re talking about people who in their elder years did some really cool stuff. And you talk about in the beginning of the book that you had an interview with Chance the Rapper that kickstarted the idea for this book. So how did Chance the Rapper get you thinking about old people who are doing cool things in the winter of their lives?

Mo Rocca: Well I think that there’s a meaning behind any joke you tell, whether it’s a traditional joke or even a jokey question. And I’m a panelist on Wait, Wait, Don’t Tell Me, which is NPR’s news comedy quiz show. I’ve been on it for a long time. And back in 2015, Chance the Rapper came on as a guest. And it was a really big crowd that turned out in Millennium Park in Chicago. And those of us on the show were kind of quizzing him on how you write a rap. And I thought, oh, here’s a hokey question I can ask him that’ll be an easy laugh. And I said, because at the time I was 46, I said, I’m 46. Is it too late for me to become a rapper? And it got a laugh, kind of an easy joke. But he looked at me dead on seriously. And without skipping a beat, he just said, I don’t know, some people might say it’s too soon for you to become a rapper. And people laughed and the conversation moved on. But I was kind of thunderstruck because I realized in that moment that I’d fallen into the trap of thinking of myself as kind of over the hill at 46.

And now I’m not suggesting that I’m going to become a rap star. But I think what he said to me had a lot of truth in it, which is that as you get older, you’re only gonna become more likely to have something meaningful to say, something to express creatively. And I’d fallen into that trap of thinking of life as kind of a series of sort of doors closing, of exits being shut off and of diminishing opportunities. And again, I was 46 and it’s kind of nuts. So my eyes were opened. And I was also kind of embarrassed that even though it was just a jokey question, that it came from a place of me thinking of myself as maybe past my prime.

Brett McKay: Yeah. I think a lot of us put those limitations on us because we have this idea in the culture that, okay, if you’re gonna be a great artist, you got to do it when you’re in your 20s. Or if you’re gonna start up a startup, you got to do it in your 20s or 30s. But you highlight a lot of great people who did some really amazing things in the second half of their life. So besides being on a panel for Wait, Wait, Don’t Tell Me, you’re also a correspondent for CBS Sunday Morning. So you get the opportunity to interview and spend time with people from all walks of life. And in your book, you talk about how you really, like you enjoy speaking to all these people, but you really enjoy speaking to the older ones. Why is that? What do you like about elderly people?

Mo Rocca: I think there are a few things at play. I think that older people tend to have better stories for one thing maybe simply because they’ve lived longer. But there’s also something that happens where people who are older generally are more comfortable in their skin. And I find that when I interview them, I have to go to them. They’re not playing up to me. So even if we’re talking about a movie that maybe they’ve been in, they’re not really overly eager to sell it to me. And that makes the conversation more interesting. I think they realize if you’re 80 and you’re in a movie, okay it’s cool, but it’s not high stakes. So they’re just kind of where they are and I had to come to them. I did this cooking series for about four years called My Grandmother’s Ravioli, where I went around the country learning to cook from grandmothers and grandfathers in their kitchen. And what I learned through doing that is that the older you get in general, the less you care about what other people think of you, which I think is where we all wanna be. And so it’s not a coincidence that my co-author John Greenberg and I could fill this book with stories of people accomplishing great things late in life, because I think as you get older, you’re more unfettered.

You’re more just willing to go for it. In my experience, I think younger people tend to crowdsource not only their decisions, but kind of who they are and their personalities. I know I did it. You try on different personalities. You’re figuring out who you are. But I think a lot of the qualities we ascribe to younger people about, oh, he really goes it alone or she really does it her way. They’re really more applicable to older people.

Brett McKay: Yeah, I’ve noticed that too. And I’ve noticed as well when I interact with older people, they lack self-consciousness, but in a good way. My grandfather passed away a couple years ago. He’s 100. And we were at the funeral and we were looking at photos of him from his life. And I was talking to my cousin. And I said Grandpa, he just didn’t seem like he was thinking too much about himself all that often. And he’s not the kind of guy that would need to download the Headspace app and meditate and figure out. It wasn’t like he wasn’t that he was shallow or anything and that he wasn’t curious, but he just wasn’t thinking about himself. And I find that incredibly refreshing in a culture where everyone’s just constantly thinking about themselves and where they stack up compared to everyone else.

Mo Rocca: God you know it’s so funny. I’m trying to think this is gonna be a little sloppy because I haven’t worked it out. But it’s almost like the camera is just shooting out, right? They’re not looking at the reversal shot. They’re not looking at the monitor, which would show you what the camera from the other side is looking at. They’re just outward facing. And I think it’s just easier to do, to just act, just like do stuff when you’re not hung up on how you look doing it.

Brett McKay: I agree. So let’s talk about some of these Rocktogenerians you highlight in the book. And you start off with one of the most famous Rocktogenerians of all time, Colonel Sanders of KFC fame. This guy is a global brand icon, but he didn’t start out that way. So what is the Colonel’s story? What was his life like before he became the colonel?

Mo Rocca: Well, it may be a surprise to some people. He was a real person, Harland David Sanders. He was from Kentucky. He grew up very, very poor, had a seventh grade education from early on, was working to help support his family as a young man. At one point, he was a midwife. He did whatever he could. By the time he was in his middle age, he had a shell gas station/chicken and biscuits joint in the small town of Corbin, Kentucky. He was doing fine. He was getting by. But then in the 1950s, a highway cut through Kentucky. It bypassed his restaurant, kind of like what happens to the Bates Motel in the movie Psycho. This has a much happier ending. And the bottom fell out of his business. He had to sell it at a loss at auction. He was 66. He was living off of Social Security, $105 a month. He could have subsisted. He could have just continued on and probably survived in some way. Instead, he got in his car with two pressure cookers, a bucket of his secret recipe of 11 herbs and spices. And he drove from town to town to town, from restaurant to restaurant, cooking for people, hoping to hook them on his chicken.

And within eight years, he was the face of a Kentucky fried empire, over 800 outlets worldwide. And what I like about the story is it’s so forward moving. I mean, even him getting in that car, I mean, that’s the perfect Oscar montage, right? Like if it’s you did the Colonel Sanders biopic, but he just does what he has to. And he just gets in the car and he drives. And I think there’s something so significant about that. So this wasn’t, and there are in the book, this wasn’t an artist sort of pursuing something creative, which is wonderful. This was somebody who had to survive and just did what he had to do. And there’s something so bold about that. And it’s funny ’cause the story has been told a lot through the years in various ways, but it never gets old.

Brett McKay: Yeah, it doesn’t. And like you said, the way he built his business, he just drove around from town to town, trying to sell franchises with his recipe and it became a success. And eventually what happened is he’s able to sell the whole company for $2 million in 1964, which is about, I think it was about $20 million in today’s money, accounting for inflation. So that’s a lot of money. And then after his success, he lived a pretty modest life. Like he just did this stuff to make a living. It wasn’t anything more than that.

Mo Rocca: Yeah, it wasn’t like some big dream or something. This is this thing he had, this recipe, and he had to survive and he did live modestly. And he actually didn’t eat much chicken. He had a diet that he hoped would take him to 100. He made it to 86, but it involved eating sardines each morning. And I do think about that when I’m going food shopping and I look at the sardines now, I think of Harland David Sanders. But he testified in front of Congress about aged people and said a man will rust out sooner than he’ll wear out.

Brett McKay: So you also highlight some men who came out of retirement to fight in wars. And the first guy you talk about is Samuel Whittemore. This guy’s story is incredible. Tell us about Samuel Whittemore.

Mo Rocca: Well, this, I mean, I love these stories because I didn’t know them before. And when we dug into this, I said I wanted to include soldiers because what could be more counterintuitive for an older person to do? And so Samuel Whittemore, before we were the United States, he had served the crown in America as a royal dragoon, which just sounds really cool. He’d been in the French and Indian wars. But the Stamp Act of 1765 really converted him to a revolutionary. He was very fervently pro-independence by the time the American Revolution started with the Battles of Lexington and Concord in April of 1775. And on the very first day of battle, when Samuel Whittemore was already 78, he was there on the front lines. He picked off between one and three redcoats before he was shot in the face and had one of his cheeks blown off and then was stabbed in the head by a redcoat and left for dead.

He survived against all the odds and he lived another 18 years. So this guy, I mean, we put in the book that, I mean, Clint Eastwood, who was 78 when he was in Gran Torino, this would be the perfect biopic for him. It’s just an amazing story. And of course, Samuel Whittemore’s family did not want him doing this, but he felt so ardently pro-independence, he just couldn’t help himself. And he became a legend, understandably. I mean, really, half his face blown off and stabbed in the head and keeps going.

Brett McKay: That’s great. And you had the chance to talk to General Wesley Clark and you asked him about this guy. It’s like, why would he come out of retirement? He’s 78 years old. He’d just be sitting on the porch in his rocking chair. And his answer he gave you, it surprised you.

Mo Rocca: Yeah. Well, General Wesley Clark was unfamiliar with this story and with another story we tell, which is about John L. Burns, a 70-year-old veteran of Gettysburg who was, almost kind of spooky music here, born the year that Samuel Whittemore died as if passing the baton, or I guess in this case, the rifle. And John L. Burns became the only civilian known to have fought at Gettysburg and certainly is the only civilian with a monument to him at Gettysburg. And both those stories were unfamiliar to General Clark. And he said he could understand because when he, as a young man, had been injured in Vietnam, when he woke up the next morning and he looked around at other wounded soldiers, he immediately felt a sense of fraternity. He felt like that that was the initiation into this lifelong fraternity and service. And so everything changed with that injury for him. And he believes that the fighting spirit really intensifies with age.

The fervor only grows stronger. And that part, I mean, I was fascinated by it. And I suppose, yeah, I was surprised by it. And I was also, I have to brag here, happy that I could tell him these stories, which he was unfamiliar with.

Brett McKay: And yeah, that Burns guy, he was interesting. So he’s a civilian and the war was basically in his front yard at Gettysburg. And he’s like, well, I’m gonna go there, take my musket. They gave him a rifle and he saw action. When he became famous and he kind of, he didn’t handle fame very well. I think he kind of let it get to his head.

Mo Rocca: Yeah. I think he was apparently kind of blustery. I mean, one of the funny things, by the way, let’s just, I had to add is that he had fought as a very young man in the battle of, in the war of 1812. But by the time the Mexican-American war came along and he tried to enlist in 1846, he was already too old. So cut to 1863 and he’s really too old as far as the military goes. And he takes this kind of sinecure of a job as a constable and it happens to be in the town of Gettysburg. So the war wouldn’t let him go to it, but the war came to him in a sense. So, I mean, as luck would have it, he’s in this little town and the biggest conflict of the civil war happens to arrive on his doorstep. And so he grabs his very outdated uniform, his very outdated artillery. His wife is like, don’t do this. And he’s like, sorry, gotta go. And he eventually, it’s, I believe with a, I might have this wrong. It’s a Wisconsin or a Michigan militia. He manages to fight with them and he does indeed kill, I believe, three Confederates. And that night he’s sort of stranded. When the Confederates find him, he manages to convince them that he was just out and about looking for his wife, why he would be wearing that, who knows, but they let him go. And he meets Lincoln when Lincoln comes to Gettysburg later. And yeah, he becomes a real braggart, really blustery. Eventually he comes to dementia and is found wandering the streets of New York city and dies a few years later.

Brett McKay: So what’d you take from these guys?

Mo Rocca: I took, I was inspired by their sense of public service, their duty to country when they were fighting for a world that at best they’d enjoy for a few years. And I find that extremely powerful. People who put their butts on the line and these two guys did really, truly, I mean, put their lives on the line fighting for something that they believed in, which even if they were successful, they would only reap the rewards for a very short time. And that is extremely powerful. I mean, young soldiers, young civil rights activists, those people are heroic, of course, because oftentimes they end up losing what could have been long lives at a very early age. But there’s something in a very particular way that’s very, very profound, I think, about older people who dedicate themselves to public service and in this case, quite literally fighting for their country.

Brett McKay: So as you mentioned earlier, there’s this romantic idea that if you wanna do your best work as an artist, writer, painter, musician, you got to do it when you’re young. I think it comes from the romantic era with Keats and Byron. Like if you don’t get it before you’re 30, you’re hosed, you’re never gonna have a chance. But you highlight several artists who did some of their best work late in life. And I wanna talk about the architect, Frank Lloyd Wright, because I live in Tulsa, Oklahoma, so we’re not too far from the Price Tower, the only skyscraper that Frank Lloyd Wright did. So he experienced early success. He had some early success, but then his career kind of sputtered out. Tell us about that.

Mo Rocca: Well, I mean, Fallingwater, this home that he built for a department store family owners in Western Pennsylvania, not terribly far from Pittsburgh, quite literally on a stream, on a falls, built around the water and the rocks, integrating nature into it, put Frank Lloyd Wright on the cover of Time magazine, which then was a really big deal. So Frank Lloyd Wright was already a great innovator, seen, hailed as a great innovator and master by his middle age. But then the world of architecture moved on and he was seen as yesterday’s news, certainly as the international style came into vogue. And he was in his late 70s when he received the commission from the Guggenheim family for a new museum in New York. He was 84 when he submitted the design for it. And he had the leading artists of the day, those who would be exhibited in that structure, completely in opposition to him because they saw the design, which was actually a design that he resurrected from a Maryland car park, believe it or not, that was gonna be in the, I always mispronounce this, the Catoctin, I think I have it right mountains in Maryland, that hadn’t happened earlier. He had taken this design and he sort of pulled it out and refreshed it for the Guggenheim museum And these artists saw it and said, this is more about the architecture than our art. This is unsuitable for us, these curves.

These curved walls are not ideal for exhibiting our art. So he really was up against it. He had, the leading artists of the age saying, you’re past your prime. What you’re doing is wrong. He persevered. And that museum is as much a part of the environment of New York City and of Central Park. It sits on the edge of it, as Fallingwater is to Western Pennsylvania. So, I mean, I think it takes… Certainly Frank Lloyd Wright had an ego, but it takes a sense of self along with a great talent to push through this idea, Brett, that you’re talking about, that you basically have an era and that’s it. Frank Lloyd Wright was too much of an artist and believed too much of it, in himself to not push through that. And I think it’s that pushing through that I really admire in a lot of these people and people in life in general, who buck up against this idea that your time has passed gracefully bow out. Frank Lloyd Wright was not gonna allow that to happen to himself.

Brett McKay: Yeah. He even wrote a letter to all these artists who are saying, Hey, get out, stop this. He’s like, yeah, just take a hike, I’m gonna do it. You guys don’t know what you’re talking about.

Mo Rocca: Yeah.

Brett McKay: So you gotta harness a little bit of that grumpy old man to get your vision happening. So don’t sell yourself short, even if you’re old. You also talk about… Oh, go ahead.

Mo Rocca: Yeah. If I may interrupt for one sec. I also have to say that it’s funny because the cult of likability is so powerful, and as somebody who works in tv I understand how powerful it is. And in putting this book together, we did think, Frank Lloyd Wright isn’t very likable. So.

Brett McKay: Yeah.

Mo Rocca: So we actually debated it, but ultimately the willfulness, the sheer willfulness of Frank Lloyd Wright made the story irresistible.

Brett McKay: Yeah. He knew who he was. Like he was comfortable in his own skin, so maybe he was a bit of a curmudgeon. That’s okay. We’re gonna take a quick break for a word from our sponsors. And now back to the show. You highlight a few writers. One you highlight is Jorge Luis Borges, the Spanish author, who’s famous for his surreal mind bending short stories. But in his sixties, he started to lose his vision. So how did he turn losing his vision into an asset and begin a new phase in his career?

Mo Rocca: Yeah. Well this is in a section of the book called Loss into Gain. And it’s something that a few of the people have in common and latent life achievers, which is that whether by design or by instinct, they turn loss into gain, they look at endings as beginnings. And it’s almost as if obstacles force them to sort of become reborn. And it’s almost like, I don’t know, my mother has a real green thumb. And sometimes they see with this grapefruit tree that I… As a kid I planted and, and she keeps in her apartment still, 45 years later. She said, I’ve gotta cut this branch off so it’ll grow much stronger. And that’s sort of what I think about. But then the plant, will actually become healthier. Borges has had been known for what were called fictionese for short stories. So not the poetry that he became even more famous for later. But as he began losing his sight in the ’50s, it became harder for him to write. And so instead of just giving up altogether, he switched from these short stories to poetry to burs because this, he could compose and he could compose in his head while he was walking around. And so that’s what he did. So it opened up a whole new vein, a whole new avenue for him.

Brett McKay: And Borges talked about how he looked to other famous blind poets. Homer was supposed to be blind, and then Milton, Milton was blind and he did Paradise Lost.

Mo Rocca: Exactly. And then of course, Borges ended up writing about both of them in his own work.

Brett McKay: Yeah. And then another artist who, same sort of thing, he experienced a loss, but he turned into a gain. Matisse, my daughter’s got Matisse things in her, hanging up in her bedroom.

Mo Rocca: You know, I love this because Matisse was already hailed as a great modernist by his middle age. But in his ’70s, cancer robbed him of the ability to paint. He could no longer sit upright, he had to recline in a wheelchair or in a bed, but he was not content to just sort of sit around, receive visitors and sort of play a highlights reel of his greatest hits in his mind or to others. So instead he traded his paintbrush in for a giant pair of scissors and began cutting big shapes out of colored paper. Paper that had been painted. He still had assistance with him and he would have them pin these paper cutouts to the walls of his room. And I’m lucky enough to live in New York where MoMA, the Museum of Modern Art, has the swimming pool, one of the great paper cutout works of art remounted there.

And you can see up close lots of little pinholes because he was still very meticulous about where they were positioned. Move it this way, move it that, and move the pens with it. However, the work itself, and I think this is very significant, there’s something childlike about it, not childish, but childlike. The bright colors, the big shapes. And Matisse himself viewed the work as a second life for him and a kind of return to childhood because there was, he said, a lack of complication in the work. It was unburdened by too much thought. And I think a lot of these stories share that with the Matisse story, which is people returning to their childhoods in different ways. Sometimes literally like the writers Frank McCourt and Laura Ingalls Wilder writing about their childhoods sometimes with people going back to their childhood to finish something that they started like the Queen Rock and Roll Hall of Fame guitarist Brian May who had been studying astrophysics before he became a guitar… Before he joined Queen, returning at age 60 to complete his PhD in astrophysics. So there’s a lot of this sort of returning to a first love or just even a childlike outlook that is very powerful, I think.

Brett McKay: Yeah. And I think it’s inspiring too, these guys. They embrace the limitations that come with old age. Like it’s… I think we have a culture where we’re just constantly fighting against old age. Like we’re just doing all the exercising, taking supplements and doing Botox and peptides just to fight off old age. And I get it, I understand why people do it, but there’s something kind of unseemly about it as well at the same time.

Mo Rocca: Well, I think a lot of it ends up making people actually seem older. In a weird way, right?

Brett McKay: Yeah.

Mo Rocca: Like I think the people who embrace their age and their aging actually seem more energetic and youthful.

Brett McKay: I think so…

Mo Rocca: And certainly more at peace.

Brett McKay: Yeah. So find out how you can turn your limitations into assets like these guys. You also highlight several people in the book who did amazing work throughout their lives, but they weren’t recognized for it until they reached Elderhood. And one of these guys is Tyrus Wong. I never heard of this guy before until I read your book, but this guy’s an incredible story. What’s Tyrus story?

Mo Rocca: Well, we wanted to include people who didn’t necessarily accomplish great things in late life, but were acknowledged before they died. It’s sort of the reverse Van Gogh, like, you know, van Gogh great artist, dies very young, largely unrecognized in his time. And to me, there’s something very sad about that. You wish that some people that died young and were recognized later could kind of come back from the dead just so that they could be like, wow, people really did actually appreciate what I did. These stories, there are three that are like the opposite of that, including Tyrus Wong who lived until 106, and towards the very end of his life finally received recognition. Tyrus Wong had grown up extremely poor in China, so poor that in his village they had to hang the poultry on ropes from the ceiling so that the rats couldn’t get to them on the dirt floor.

When he was eight years old, his father took him to America. He never saw his mother and sister again. He was for a month on Angel Island where immigrants would come in in California and near Los Angeles was separated from his father for a month, which alone would’ve been traumatic, right? You leave your mother and your sister and you’re just with your father and then you’re separated for a month. The father then got a job as a laborer, but saw talent in his young son and earned the money to send his son Tyrus to the Otis Art Institute in Pasadena. And he quickly excelled there. As a young man. He was actually exhibited at the Art Institute in Chicago, and he made his way to Walt Disney to Buena Vista Studios. And there he worked on the movie Bambi. Disney had already had a big success in feature films with Snow White and the Seven to Dwarfs.

But Bambi had a completely different look. Instead of clear, bright lines, people will remember that it’s much more evocative of the forest and the moisture. And that was due to Tyrus Wong who was doing backgrounds. And Walt Disney himself was so impressed that Tyrus had sort of combined the Impressionists whom he’d studied with the brush work of the Song Dynasty of the Chinese Song Dynasty. So everything was much more impressionistic. There weren’t clear stark lines. It was a completely different look. However, he was never… First of all, he never even met Walt Disney himself. He ended up getting laid off from Disney after a strike by animators, even though he himself had not been striking. And he just went on without ever having received recognition for the look of what became a blockbuster. He ended up then continuing his art at different studios and then making kites by all accounts, he had a very, very happy life with his wife and his two daughters.

In his 80s though, close to 90, suddenly Disney made him a legend and a whole cascade of honors followed, including a documentary. And he died at 106 and he had been working very, very late in life. But his story, and two others in this section of the book have one thing in common, very, very long marriages that they credited with getting them through very rough patches in life. Tyrus Wong was married, I believe, for 58 years. And if you’re gonna continue pursuing something certainly like art and you’re not gonna be really recognized, you are gonna need somebody. I think these stories tell us who is gonna be your champion in life and is gonna help you get through those downturns.

Brett McKay: I imagine too, it helped having another way to, I don’t know, feel good, like another mission in life. If the only thing he had going in his life was his work, didn’t have family, well if your work didn’t work out like you’re hosed, you don’t have another, another thing to fall back on.

Mo Rocca: I think that’s right and I think you can even see it in the photographs of Tyrus Wong. You can see, first of all, when he talks about his wife and how taking care of her as she went into a slow decline and died years before he did, was the most important work of his life. And he means it. And yeah, it’s a beautiful story. And actually one of my colleagues, Tracy Smith, who was a correspondent at Sunday morning, actually interviewed him before he died. And that’s how I learned about the story. And you just, you can just feel the love coming off the guy.

Brett McKay: Another person you highlight that worked tirelessly to build a career but didn’t experience success in recognition till later life was the actress Estelle Getty, better known as Sophia from the Golden Girls. She had dreamed of being an actor from a young age. And she took steps to make that happen, but it didn’t really happen for a long time. Tell us about her career.

Mo Rocca: Well, you can’t do a book like this and not include at least one Golden Girl.

Brett McKay: That’s right.

Mo Rocca: I think the book would’ve been banned or something if they hadn’t. So she was the one, all four were pretty great. But Estelle Getty was such an interesting story and she played, as you pointed, she played the mother Sophia on The Golden Girls, a hilarious character. But the other three Golden Girls had all had big careers from early on. And, I think it’s fair to say they’d really put their career center and good for them. Estelle Getty had actually wanted to act from a very early age. She grew up in the lower East side of New York. Her father, who was working class, would take the family to the Academy of Music when she was just a kid to see vaudeville and early talkies.

She had gone to the Catskills to wait tables and try her hand at standup comedy. She married when she was 23. She had two sons. And raising a family just made it impossible for her to pursue her career full-time, at least at that time. She did take whatever small parts in plays she could get, by the time she was in her 50s, she joked that she was just getting parts as mothers, as Irish mothers, Jewish mothers, Italian mothers. She once said she played everyone’s mother except Attila, the Hun’s mother. And when her kids went off to college in the ’70s, she kind of turned her focus back and said, I’m not done yet. And she was in her 50s by this point and she did something I think that’s really, really pivotal here that characterizes a lot of these latent life achievers.

She went to see a play off Broadway by a then unknown playwright named Harvey Fierstein. And she liked it and she went backstage and she basically forced herself on the playwright. She said to him, I want you to write a part for me. And I think he was so taken aback and charmed that he did it. He wrote apart for her as the mother in what became Torch Song Trilogy, which was a very, very big play on Broadway, very important in the eighties. And that became her Broadway debut. And I think she eventually did it in a touring company in Los Angeles. And that’s how she got noticed. But I think it was that kind of proactivity of saying, Hey, I’m really good. You need to write something for me instead of being sort of coy about it. And so she was 62 when she was cast in the Golden Girls as the mother. She had never been on network television before and she became arguably one of the funniest characters of the last 40 years, 50 years on a sitcom.

Brett McKay: Yeah and I think the lesson there is sometimes you’ve just gotta put it on the line and ask for what you want. ‘Cause it could change the whole course of your life. What happened to Getty’s career after Golden Girls?

Mo Rocca: She did all sorts of movies. I’m not sure how Stop or My Mom Will Shoot you became such a funny joke maybe because the title’s so ridiculous and it’s with her and Sylvester Stallone. But she continued working. She eventually had dementia and, by the end of her run on the Golden Girls, she was having a lot of trouble. Partly it was nerves remembering lines, but she made it work. But I mean, it’s weird to put it this way, but she really deserved it after living the life she had and never giving up on this dream. It really was the ending that she deserved.

Brett McKay: Another actor that you talk about that had late in life success. And when he showed up in the book, it’s like, no, that’s not right. This guy has always been famous. Morgan Freeman. It’s hard to believe that he was a late in life success ’cause You just think Morgan Freeman has always been a big star, but he wasn’t. What was his early career like?

Mo Rocca: Well, I was sort of familiar with Morgan Freeman from having interviewed Rita Moreno back in 2013. And it forced me happily to revisit the Electric Company, a show I loved growing up. I was not a Sesame Street person, I was an electric company person. And Rita Moreno and Morgan Freeman had been on it together, but they had had opposite career trajectories. She had already been a star from West Side Story. And she had taken this role on a PBS show because she’d moved to New York with her husband and daughter and thought, all right, I’m in my 40s, which at that time was considered old for actresses. I mean, it’s ridiculous, but she thought this will be a nice job as I raise my daughter. Morgan Freeman was also on the show about the same age, actually, I think. Is he a little bit older? I think they’re about the same age.

And he had been struggling for a long time and he didn’t love being on the electric company. And there was actually some tension between them. They ultimately became very good friends and remained close. But, so their stories were sort of intertwined and doing this book, you know, it was interesting to learn about how Morgan Freeman had come up. He served a stint in the Air Force. He went to LA to become an actor, but he always had integrity. He had quit a job with the San Francisco Opera that included what he felt was a denigrating stereotype of an American Indian. He had walked out of a television commercial audition because there was a part called the Jew actually called the Jew. So he had a real moral backbone from the beginning, even when he was struggling, really struggling.

And he said, there was a great possibility he could have ended up homeless because he was putting everything he could into acting and if it hadn’t succeeded, things would’ve looked really bad. So he really struggled. And on electric company, he was frustrated and Rita Moreno said, look, we didn’t know how much talent this guy had. It was then after that that he made his feature film debut when he was well into his 40s. It was in the Robert Redford movie Brubaker. And then in his early 50s, he had an Oscar nomination for a movie called Street Smart. But then he had a real banner year that included both Glory, which he’s co-staring with Denzel Washington in Driving Miss Daisy, when he was 52, although he was playing a 60-year-old then. But it’s very funny because an interviewer once asked him about the struggle of being an older actor.

And he said, I can’t tell you about the struggle of being an older actor. I can tell you about the struggle of being a younger actor. And I think he… There are actors out there, I think Angela Lansbury was, even though she had been a success early on, but there are actors who grow into their roles, who somehow they’re meant for real success later because, maybe because in the case of Morgan Freeman, that great voice and that gravitas he had, I mean, you can’t play God when you’re in your 20s.

Brett McKay: Right.

Mo Rocca: And no one has played god like Morgan Freeman or sounded like it. Since he turned 60, he’s been in 80 movies. I mean, that is the opposite of what we think of as a Hollywood career.

Brett McKay: Yeah. Like Clint Eastwood had, I mean, he was a big star when he was young, but I’m always amazed that he’s kept on producing and acting even in his 70s, 80s, and 90s.

Mo Rocca: Well, I think Clint Eastwood and actually I’m not bragging here as a college kid, I got to meet Clint Eastwood and my god what star wattage, but Clint Eastwood is amazing because to be this international film star known for Dirty Harry and Spaghetti Westerns and then just say, no, I wanna make movies and I wanna make good movies. And we forget now but there were so many naysayers early on, and Clint Eastwood has made so many different kinds of movies and I mean, talk about somebody who is not concerned with what other people think of him and just does it and has continued to grow. And like we were talking about before, just not respecting this idea, this artificial idea that you have a sort of an arc that you kind of have to observe that you do one thing and then when you’ve peaked, that’s kind of it. And no, I mean, it’s amazing.

Brett McKay: So we gotta talk about Mr. Pickles. Why did Mr. Pickles end up on the octogenarian list.

Mo Rocca: Well, we wanted to… John and I wanted to include personal milestones and because, not to make them all career or even creative or entrepreneurial, or sports, late in life achievement, but personal ones like marriage and parenthood. And Mr. Pickles is a Houston Zoo tortoise, I say is because he’s expected to live for many more years, like most radiated tortoises. And he became a first time father at 90. And, you were impressed by Al Pacino fathering a kid at 83. He was just a kid in comparison with Mr. Pickles. Mr. Pickles has, by the way, the three kids are named Jalapeno, Dale and Gherkin. Lucky he’s gonna live a long time. He could have a lot more kids. He could become the Nick Cannon of tortoises.

Brett McKay: Yeah. He’ll get to meet his grandkids too. So are there any, we’ve talked about some lessons you’ve learned from all these people we’ve talked about, but are there any through lines you found in these stories? Any overarching takeaways that you found while writing this book?

Mo Rocca: Yeah, and I’ve mentioned some of them, but I think the first one will sound, I think really obvious, but these are people who are very much in it. They’re not fixated on the past, that’s for sure. And this is what surprised me. They’re not fretting about the future. I always thought, even as I got into this project, I thought the less time you have on the other side, the more frenetic you’re gonna become about Oh my God, time is… And while there certainly is an urgency to many of these stories, there’s nothing frantic or fretful about them. So they’re neither fixated on the past, nor fretting about their future. They’re very present minded and in it, they’re very in it, which is where I think we all wanna be, which is why we should spend… And this is a note to myself, spend a lot less time on social media. So you can really be in it and not distracted. I think, as I said, these are people who were not overly concerned with what other people would think. And I think another one of these patterns is kind of a return to an early love to unfinished business.

Brett McKay: I love that. Well, Mo, this has been a great conversation. Thanks so much time. It’s been a pleasure.

Mo Rocca: Brett, thank you very much.

Brett McKay: My guest today is Mo Rocca. He’s the co-author of the book, Roctogenarians. It’s available on amazon.com and bookstores everywhere. Check out our show notes at aom.is/lateinlife where you can find links to resources. We can delve deeper into this topic. Well, that wraps up another edition of the AOM podcast. Make sure to check out our website @artofmanliness.com, where you’ll find our podcast archives. And while you’re there, sign up for a newsletter. You have a daily option and a weekly option through both three. It’s the best way to stay on top of what’s going on at AOM. And if you haven’t done so already, I’d appreciate if you take one minute to give us a review on the podcast or Spotify helps out a lot. And if you’ve done that already, thank you. Please consider sharing the show with a friend or family member you would think get something out of it. As always, thank you for the continued support. And until next time, this is Brett McKay, the Art of Manliness podcast, but put what you’ve heard into action.

This article was originally published on The Art of Manliness.

You have a relationship with family, with friends, with a romantic partner. You may not have thought about it this way, but you also have a relationship with your job — a quite serious one, in fact; after all, you spend a third of your life working.

Just like the relationship you have with your significant other, there are ups and downs with your relationship with your job. It can start out with exciting honeymoon feelings, but along the way, you can end up drifting apart from your job, lose interest in it, or not feel appreciated. And there can come a time when you start wondering if you and your job should part ways.

Here to help you figure out if you should break up with your job is Tessa West, a professor of psychology and the author of Job Therapy: Finding Work That Works for You. Tessa interviewed thousands of people who have recently switched jobs or undergone career changes and found that there are five forms that job dissatisfaction typically takes. Today on the show, Tessa shares those five job dissatisfaction profiles, and how to know when you need to try to move into a new role within your company, or move on altogether and even change careers.

Resources Related to the Podcast

• Tessa‘s previous appearance on the AoM podcast: Episode #834 — The 7 Types of Work Jerks (And How to Deal With Them)
• AoM Article: 30+ Questions to Ask Yourself Before Leaving a Job
• AoM Podcast #578: Figuring Out If You Should Change Careers (And How to Do It)

Connect With Tessa West

• Tessa‘s website
• Tessa‘s research lab

Listen to the Podcast! (And don’t forget to leave us a review!)

Listen to the episode on a separate page.

Download this episode.

Subscribe to the podcast in the media player of your choice.

Read the Transcript

Brett McKay: Brett McKay here, and welcome to another edition of The Art of Manliness Podcast. You have a relationship with family, with friends, with a romantic partner. You may not have thought about it this way, but you also have a relationship with your job, a quite serious one, in fact. After all, you spend a third of your life working. Just like the relationship you have with your significant other, there are ups and downs with your relationship with your job. It can start out with exciting honeymoon feelings, but along the way, you end up drifting apart from your job, lose interest in it, or not feel appreciated. And there can come a time when you start wondering if you and your job should part ways. Here to help you figure out if you should break up with your job is Tessa West, Professor of Psychology and the author of Job Therapy: Finding Work That Works for You. Tessa interviewed thousands of people who recently switched jobs or undergone career changes and found that there are five forms that job dissatisfaction typically takes. Today on the show, Tessa shares those five job dissatisfaction profiles and how to know when you need to try to move into a new role within your company or move on altogether and even change careers. After the show’s over, check out our show notes at aom.is/jobtherapy.

All right, Tessa West, welcome back to the show.

Tessa West: Thank you again for having me.

Brett McKay: So we had you on last time to discuss your book, Jerks at Work, and how to deal with those jerks you sometimes encounter at the office. You had a new book out called Job Therapy, where you dig into our relationship with our job. And I think a lot of people typically don’t think about having a relationship with their work. A job is just something you do. What got you thinking about work in terms of a relationship?

Tessa West: Yeah, this is a great question. I think a bunch of different things, but just to kind of give you a little bit of background, I’ve been teaching a close relationships class at New York University now for 15 years. And so I’ve been thinking about how we go from the kind of initial attraction stage, so the first date, which is a lot like a first interview, all the way through that stage where we get a little bit itchy and we start drifting apart from our partner, the ambivalence, those feelings we have that are a little bit complicated, the emotional ups and downs, and all the way through the end of a relationship when we decide to break up.

And what I noticed in the past couple years is that there’s just been kind of this shift in how we talk about work using these relational concepts. And so every time I taught, and this was last semester, we would talk about what can go wrong on a first date. And at the same time in my consulting and in my research, studying the workplace, people were asking me the same types of questions about interviews. And when they were trying to process whether they should break up with a job that they’ve been committed to for a long time, they would ask me questions about identity loss, like this hole in my heart, how am I gonna fill it? And that’s the same language we’re using around marriages.

And so, I started to kind of see these two worlds I live in converging and these concepts starting to overlap in ways that I think most of us had never really thought of before. And that’s really when I decided to adopt a relational perspective to think about your career as just another thing that you have a relationship with, much like a person.

Brett McKay: So, a lot of people are unhappy with their current jobs, but they’re unhappy for different reasons. If you ask five different people why they don’t like their job or their career, they might give you five different reasons. And you took a deep dive to find out what are the top reasons people are unhappy at work. So, you did this massive survey. What did you discover?

Tessa West: I think most of us, if you ask someone why, they don’t truly know. And so, you kind of have to ask more indirectly about how they’re feeling. And so, what I found was that a big chunk of people, especially those who’ve been working for a really long time, they have a crisis of identity. They used to love this thing. And the thing is, tends to treat them very well. The career does. But they don’t feel as strongly identified with it as they used to. And there’s a lot of shame and guilt that goes along with that. So, that is the crisis of identity person. Kind of in a similar vein is the person who’s drifted apart from their job. And this is the person who’s pretty nostalgic about what that job used to look like. It could be that the whole industry has changed. Maybe it’s just this company. But it’s a little bit like waking up and looking at your spouse in bed and thinking, who are you? I don’t recognize this person anymore. And for those people, they really have to dig deep to understand kind of what is the source of that drifting apart. Is it really just the job or is it also them?

And then the third is the person who’s stretched too thin. And I actually wrote this chapter for everybody. I think we all know what it feels like to be juggling multiple roles or tasks or to be task switching all the time that we’re not getting anything done. And so, those individuals tend to have taken a few missteps along the way in terms of absorbing roles or taking on what I call high visibility roles that they think will get them a raise or promotion, get them on the map, so to speak. But they end up just kind of being all over the place or interrupting themselves constantly at work.

And then the last two chapters are for people who are not getting the love back from their careers. So there’s the runner up. We all probably, if you’ve worked long enough, you know what it feels like to get passed up for raises and promotions. And you don’t really know why. There’s a huge kind of gap there between their understanding of what they’re doing wrong and what leaders think they should be doing instead. And then the underappreciated star, the person who gets a lot of nice Slack messages or emails, but the real rewards aren’t coming and they’re often kind of dangled in front of them in some sort of like hypothetical future, if you stick here long enough, you’ll get that president job in a year and then eventually the C-suite and once we have enough money, you’ll get that bonus. And so, they really have to figure out if they can get compensated better elsewhere and how much organizations actually even really care about hiring stars. So, those last two chapters are really about trying to get the love from that relationship with your career back that you are feeling towards it.

Brett McKay: Okay. So, these are the top five. We got the crisis of identity, the drifted apart, the stretch too thin, the runner up, the underappreciated star. We’re gonna dig into each of these here in the conversation. But you also found before we talk about these five different types of dissatisfaction profiles, you also talk about there might be a lot of job dissatisfaction that just comes up from like daily stressors that we tend to overlook with a job. It’s not even that you don’t identify with your job anymore or you feel like you’re stretched too thin. It’s just the other stuff that we overlook when it comes to having a job that might be causing us dissatisfaction. What sorts of stressors are those?

Tessa West: Yeah. I think most of us experience a lot of low-level stress at work, but we don’t actually see how it kind of builds up and affects our happiness at work or our engagement or these kind of like bigger picture things. And I think what I did for this chapter was I ran a simple study where I asked people in the morning, what do you think is gonna stress you out today? What your biggest stressor is gonna be? And then I asked them again to do it in the evening, what actually stress you out? And there’s not a ton of overlap. And I think it’s because anticipated stressors tend to be big things. They tend to be things like a presentation I have to give, a meeting I’m really nervous about.

What people reported are what I would call like certainty-based stressors, thing that they can anticipate and then plan for. And because you can plan for those things, you actually don’t end up experiencing that much stress. You put some steps in place to make sure you can handle the thing. We call this a challenge response in health psychology. But what ends up actually stressing people out are pretty small things. And many of them, we tell ourselves we can’t anticipate, but we actually can if we’re a little bit more strategic. A commute that ran too long. Your parking space has been taken up. Your boss putting a last minute deadline on your calendar. Someone interrupting you at work. Those things that we don’t really see coming in the morning, but they end up being additive and really stressing us out.

But kind of ironically, what I found is that even for those things, if you ask someone if they’ve experienced it before, they’ll tell you, oh yeah, I experienced this all the time. They just don’t encode it as a stressful thing. And so they don’t think about it again and they don’t plan for it. But most of the time, we’ve had that last minute meeting put on our calendar. We’ve had that commute go long. We’ve had our parking space stolen and so forth. So if we just kind of keep track of these things, we can actually do a much better job of mitigating their effects on us.

Brett McKay: And what that can do, I think a lot of people, they might experience those sort of daily stressors, mundane stressors. They think, well, I just hate my career. I hate my job. Well, it might not… Maybe your career and job’s fine. You just got to take care of those things like the job or career you have right now. It’ll be great.

Tessa West: Yeah. I think we tend to catastrophize a little bit when we’ve had an accumulation of small stressors. It’s a little like anyone who’s been a parent and they have a kid who misses a nap and they just lose it completely and cry over everything. I think there’s an adult version of that, which is an accumulation of small daily stressors. They affect our health. They affect our sleep. And that in turn affects our ability to cognitively function, to regulate our emotions at work, to handle difficulties that come flying at us. And I think that we do dramatically underestimate the effects of those low-level things. And then we catastrophize and tell ourselves, oh my gosh, this job just isn’t a good fit for me. I feel really miserable right now. But because we haven’t identified the source, we attribute it to something big and existential. And that’s where I think your first step is just to keep track of those low-level things to try to correct for those before you get into the deep kind of psychological issues you might be experiencing.

Brett McKay: Okay. So let’s dig into those deep psychological issues. Let’s say you took care of all those stressors and you’re still not feeling happy with your job. Your book is designed to help you figure out why you might not be unhappy, why you might be unhappy with your job or career. And that first one you said is the crisis of identity. And this is someone who starts a job or career. It’s a good fit initially. They enjoy it at the beginning. They actually get really good at their career job, but then they start having second thoughts. So what are some signs that the crisis of identity is the reason you’re unhappy with your job?

Tessa West: So I think there’s two things that you need to do. I give you kind of this checklist of, is your career identity a central part of who you are? And a lot of people who are having a crisis of identity still say yes to that question. Things like when I think about, for me, when I think about being a professor, that’s really important to how I see myself. It’s central to my self-esteem. So you wanna measure that and you wanna measure it over time because I think we have days in which we feel highly identified with our work and days when we feel less identified. You wanna measure how stable that so-called identity centrality is over time.

But the second core piece is what we call identity satisfaction. And so you can be really identified with your career. It can be a core piece of who you see yourself as a person and hate it at the same time. Hate the fact that your self-esteem is yoked to this thing, that this thing doesn’t bring you happiness. And I think a lot of people having a crisis of identity kind of fall into that dangerous quadrant of high centrality and low satisfaction. We see this a lot in healthcare with burnout and things like that. And that can create a lot of ambivalence in people where you sort of love and hate your job at the same exact time. And that to me is the big warning sign. Not that you hate your job consistently, but that you feel like it’s a core piece of you and you’re not happy with it. And you kind of love and hate it on and off, often within the same day. In relationship science, this kind of heightened sense of ambivalence tends to be what predicts when people break up. Not so much just consistently being negative, but feeling really kind of angsty inside when you think about your career.

Brett McKay: Yeah. Your crisis of identity, that high centrality, low satisfaction. It’s like your job’s your frenemy. You love it and hate it. We’ve had podcast guests talking about that. That’s like the worst type of relationship you wanna have with somebody.

Tessa West: Yeah. It is the biggest predictor of getting into an on-again, off-again relationship. If you don’t actually sort of resolve that identity centrality and you start kind of exploring new identities before you leave, that’s really key. Otherwise, it’s just like breaking up with your ex and getting back together because you have nothing to kind of fill the void. The same thing can happen at work.

Brett McKay: Give us some more concrete examples of what it would look like if you had high career identity centrality. You think of yourself as ex-profession, but low satisfaction. What contributes to that low satisfaction?

Tessa West: It’s a lot of intermittent reinforcement at work, I think, that really does that, that puts you in that unique quadrant. It is your boss reinforcing you in a way that is difficult to predict. You don’t know when you’re going to get a pat on the back or told you’re great. You don’t know when you’re gonna get ignored or told you’re doing poorly. It’s a very unpredictable reinforcement schedule. We know from behavioral science that that’s the best way to keep people yoked to something that they don’t actually love. And so if you are getting reinforced, but if you keep track of that reinforcement, and by reinforcement, I just mean anything from a bonus or raise, those are big forms of reinforcement, to small ones like people recognizing your contributions at work. If you can’t predict when you’re gonna be positively reinforced for what you’re doing at work, then you’re gonna get really strongly pulled into that pattern where you have a hard time letting go.

In fact, reinforcement, it works on monkeys, it works on rats, it works on humans in relationships. I think it actually makes you more identified with something than even just getting positively reinforced consistently does. There’s something about the uncertainty, the lack of predictability that really keeps people tethered to these things that they don’t love. I think that’s where it gets a little bit scary.

Brett McKay: Okay. So if your identity centrality is high and your identity satisfaction is low, that might be an instance where your career is fine. Your chosen career is great. You just need to find maybe another place to do that career.

Tessa West: Yes. I think the biggest mistake people make is they act on that identity satisfaction and think they should just completely pivot to something new. And then they realize a little bit into that journey that, oh, wait, I actually missed my old thing. Well, you need to measure your centrality around that old career before you make that pivot. So if you have that low satisfaction, before you pivot, you wanna make sure that that identity centrality is consistently low for a period of time. And so you’re absolutely right. If you find high centrality, identity centrality consistently for a while, a couple of weeks, a couple of months or whatever, then you probably are just more in a place where you wanna stick with your career, but you need to find it elsewhere.

Brett McKay: Okay. What happens if you have low identity centrality with your career? Let’s say you’re a professor and at the beginning of your career, you think or you feel like this is what I was meant to do. I enjoy doing this. I enjoy being professor. But then 10 years later, you’re just not feeling it anymore. It doesn’t seem like that’s what you’re supposed to be doing. How do you go about trying to figure out what your next career is? How do you go about making that big change from professor to something else?

Tessa West: Yeah. I think the first step you wanna do, and this scares people, but I think before you quit your job, is you actually need to start dating new identities. And I probably take this metaphor too far. But you need to actually try on new identities, develop a clear sense of what your future identity is going to look like before you make any moves. And the only real way to do that, it isn’t by reading company websites or taking extra courses. It’s by networking and having 15, 20-minute conversations with people in new careers where you can do things like tell the difference between two things that sound similar but are actually super different or learn the hidden curriculum around what it really takes to succeed or learn jargon, which I know gets a bad reputation, but we use it anyway.

So really kind of exploring these new careers to develop just a clear sense of what your future identity looks like or could potentially be before you ever take that next step. I think too many of us are attempted to quit, take some time off, take some extra courses, apply for jobs before we do that whole developing the new identity thing. We think we can’t develop an identity around a career we haven’t jumped into or haven’t tried yet, but I actually don’t think that’s true at all. I think you can actually start to understand what that identity would look like should you be in it by doing this networking. I think that’s a really important kind of in-between step people need to do.

Brett McKay: Yeah, so before you quit, talk to a bunch of people who are in that career you’re thinking about. I think another thing you could do too is do some moonlighting. Maybe you wanna be a writer. Well, try moonlighting as a writer while you still have your job or you’re like, oh, I hate my corporate job. I wanna become a pool cleaning guy. Start cleaning pools and see what it’s like. Do it on the weekends, for example.

Tessa West: Yeah, you have to try it out. I meet all kinds of people who think a career would be a good fit for them because they think really big picture in terms of it. Someone wants to be a nurse who I talk to because she cares about helping people and she really wanted to just do that. But when she got trained as a nurse during COVID, so very, very little hands-on training, but then she kind of realized she hated the sight of blood and cleaning up poop, which turns out to be like 80% of your job as a nurse. And those just kind of like what is the day in the life actually look like is something that you can’t know unless you actually kind of try the job on a little bit and try it. And I think the moonlighting piece is really important. I think people are afraid to do that or they feel like they don’t have the time or the mental resources to do it, but you’re not gonna know how that new job feels, whether it fits you, unless you actually sample it a little bit first.

Brett McKay: Yeah. People can have this problem even at the start of their careers. I went to law school. I thought I wanted to be a lawyer since I was in high school because my idea of being a lawyer was like watching Matlock and law and order. And then I went to law school and I had to do my internship and I did my first internship at a big firm. I hated it. I absolutely, like I just did not suit my personality. So yeah, that can happen at the beginning. So I think I would have been better served before going to law school. Like I didn’t know any attorneys too. I just thought, I had no clue what it meant to be a lawyer. I think it would have been better served to maybe talk to a bunch of lawyers, maybe like in high school or college work there for the summer to see what it was like. That would have been helpful.

Tessa West: I think, yeah, I would add another piece of advice, which is like when you’re doing this, the temptation is to find a bunch of people who kind of know each other and network that way. So, you find a lawyer and then you ask that lawyer for another lawyer you can talk to and we call that snowball sampling. It’s a great way to network. But when you do that, you get a lot of overlapping information about a career ’cause those people have things in common with each other that might not actually reflect what it’s gonna look like for you. So you wanna actually network with people who don’t know each other, who don’t have completely shared histories or even work in the same organization. ‘Cause you wanna look for that kind of signal in the noise across all these diverse people to understand what that career could really look like. I think one big misstep people do is they talk to 10 people, all of whom have the same boss or work for the same organization and then they overgeneralize those 10 people’s experiences to what that career would look like for them. And then there’s just nothing in common. And I think you really have to really broaden your network in that early stage, talk to a litigator for you but also maybe someone who works for the county. All kinds of law just to get a little bit of sense of the heterogeneity of that career.

Brett McKay: And then when you’re talking to people you have this great question to ask to really get information you otherwise wouldn’t get to really figure out what it’s like to have this career. And the question is, before I started this job nobody told me that… And then have the person finish because then you might learn some things that you probably didn’t know and wouldn’t have even known to ask.

Tessa West: Yeah, I think I love this question. It’s based on this NPR really funny thing they did of, I must have missed that day where people talk about late knowledge that they accumulated. And I gave this survey to a bunch of people and I got like really wild answers. All kinds of things from like weird hidden norms. Like I didn’t know that I had to bring chocolate once a week to the boss to, I didn’t realize that as part of my job running this art gallery, I had to lift heavy boxes and most of the things people reported were extra roles and responsibilities that they were assumed to do that was normative to do but they were not hired to do. And I think that’s one of the main reasons why we actually drift apart from our job or have an identity crisis is because of this sort of like lack of role clarity, being asked to do random stuff that has nothing to do with the job. So you wanna get a sense of what weird randomness you might encounter should you take on this career. And I think the answers will surprise you and people are always a little bit surprised when they get asked that question, but they come up with like pretty interesting and creative answers. So that was kind of one of the more fun things I did for this book.

Brett McKay: Okay. So with crisis of identity, you wanna look at your identity centrality, identity satisfaction. So if you are still, you still have a high identity centrality with your career, but low satisfaction, maybe you don’t jump careers completely, you just find another place where you can get that satisfaction again, then if your identity centrality is low. So maybe you started your career thinking yourself as a lawyer, professor, teacher, et cetera, and you’re not feeling that anymore, that’s when you might think about jumping ships to different career. But before you do that network, ask around, figure out what it’s like with these new careers, you’re dating other careers and maybe even moonlight. We’re gonna take a quick break for a word from sponsors.

And now back to the show. Let’s talk about that second reason you’ve found that people are dissatisfied with the work and that’s when they’ve drifted apart from their job. What does that look like and how do you know that’s your dissatisfaction profile?

Tessa West: So the drifted apart person tends to think about what their career used to look like. So their happiness is anchored on the past and they’ll use very nostalgic language. I really loved it when we all worked under the same roof and now we’re hybrid. They will often… I gave people a checklist of a bunch of items. They’ll often check off a whole bunch of things that have changed at work. And the most common are the people you work with. So relationships, who your boss is who’s on your team, whether that best friend from work is still there and they recognize that a whole bunch of little things have changed but they often have a very difficult time seeing how all of these things have led to them just feeling on we at work, feeling bored and not interested and no longer motivated.

I think what’s fascinating is a lot of us tend to think that some big picture change like a restructure or a round of layoffs is what led to these things. But even the leaders I surveyed said that it’s very hard to draw those associations. So we’re left with a million kind of death by a thousand paper cuts at work, a million little things that have changed but no sense of how they all kind of work together to lead us to feel this way. And then coupled with that is a bit of an underestimation of how much we’ve changed at work, how much maybe our preferences have also changed that have contributed to this feeling. So we know we’re unhappy, we think we still like this career but we’re not quite sure why. And that’s where a lot of the soul searching goes.

Brett McKay: So what are some questions you can ask yourself to figure out whether you need to jump ship to a different career? Maybe you just gotta change things with your current career?

Tessa West: I think for the drifted apart, the main mystery here is if one type of change will happen in the workplace, is it gonna trickle down to affect a type of change that they really don’t enjoy? And whether that’s industry-wide or not. And I think for them is this a new career issue or is it just my job really comes down to has the whole industry changed? And a lot of people who feel drifted apart at work who are nostalgic for their old job really think it’s just their workplace. They think very locally about the changes, but often once they start networking and exploring things they actually realize there’s been kind of this just massive evolution of the whole entire industry and often in ways that they don’t totally anticipate.

So, one person I talked to was a school psychologist and that used to involve a lot of therapy and now it’s just testing. And why has that happened? Well there’s been some state regulations around what a school psychologist can and can’t do that has just fundamentally altered the nature of that career. It doesn’t matter what school district you’re in, you’re just gonna be doing testing all day long. People who feel it and just kind of a very much in the moment way have had AI introduced into the workplace or things like new software programs that they have to use. And so they don’t actually understand how widespread these changes are and that’s really what they have to first decide is, are there so many changes to this whole industry that I no longer recognize it and I need something completely different or is it just my place has gotten weird and different and I could actually kind of find what I used to have somewhere else.

Brett McKay: Gotcha. Yeah, I think that’s interesting. The idea of industry-wide changes causing you to drift apart. You’ve been seeing a lot of this, going back to education, a lot of teachers are quitting teaching and you ask them why and they just say, Well it’s just the profession of teaching, particularly in public schools has changed dramatically. We had to do different things like this is not the thing I signed up for when I became a teacher.

Tessa West: Yeah, there’s a huge emphasis on state testing performance and so now they all have to just spend so much time doing test prep, very little flexibility in curriculum. There’s a lot of kind of like top down direction giving of what you can and can’t teach. So teachers who really value creativity feel stifled in the classrooms. So they’re looking for jobs in which they can like kind of do that piece of it elsewhere. But I think for them the struggle is often, well where can I actually do that? Who does value that piece of me? That kind of creative curriculum building piece and then how kind of fungible is that skill into a new career and how can I talk that new career into believing me that this skill has utility in that job? And so learning kind of how to transfer skills is super important for people like that, for people like those teachers.

Brett McKay: Okay. So if you feel like you drifted apart, you need to figure out whether this is just happening at your particular job or if this is a larger thing and if it’s a larger thing that may suggest you need to jump ship to a different career pivot.

Tessa West: Yeah, absolutely. And I think you also wanna document your own changes. I talk about in the book about framing this not in terms of what you used to love and now hate but in terms of your preferences for specific types of work to kind of pull the emotions out of it a little bit. I used to prefer X and now I prefer Y. So that when you network you can kind of anchor those conversations around whether that type of task you’re interested in that preference is reflected in what people are doing in that other job.

Brett McKay: Gotcha. Alright, so the third reason people might feel unhappy about their work is the stretched too thin. And you said earlier you think a lot of people, even if they’re pretty happy with their career job, a lot of people might be experiencing this. So what are some signs that you are the stretch too thin dissatisfaction profile?

Tessa West: One of the main things is you have a really hard time rank ordering the importance of your roles at work. So, I kind of talked a little bit about like there’s two issues, there’s the role stuff, what you’re doing, what your actual job is and then how you work. The role thing I think is a real problem. I think we have our assigned roles, the roles that we’re paid to do. And then we have most of us spend like 8-10 hours a week on roles that we weren’t assigned to do, many of which we’re not even paid to do. And you need to ask yourself the question, write out all your roles at work rank order them in terms of most to least important and importance in terms of what you care about, but also importance in terms of what matters for promotion and raises and so forth.

And if you have a hard time with that rank ordering list, you probably actually have no idea what roles you should be focusing on. I think, a lot of us work in places where it’s normative to take on the role of somebody else when they’re out or if they’ve been laid off, there’s a lot of role absorption going on. But one thing that people also do is they volunteer for roles that they think will make them visible. Things like running an employee resource group or a conference committee, these kind of community building roles that are helpful but your performance on those roles are rarely discussed by leaders during promotion decisions.

And so you feel good and you get a lot of pats on the back and everyone loves you for taking these things on, but they don’t actually matter as much as you think you do. So I think you really wanna sort of critically evaluate your own roles. And then the second piece is how you actually work. Are you switching tasks so often you’re getting nothing done. And I think most of us are used to task switching. Most of us are also not very good at preventing ourselves from interrupting ourselves. And so most of those interruptions are so called self interruptions.

And so kind of figuring out what your pattern is there of like how you can actually just be more productive at work by interrupting yourself or having others interrupt you more strategically so that when you jump back into something you can actually kind of have a much more systematic workflow. I talked to neuroscientists for this chapter because a lot of why we feel stretched too thin actually comes down to the memories we form at work and our ability to kind of start where we left off has to do with how good we were at encoding what we did in the first place. And when we interrupt ourselves a lot, we don’t encode those memories of what we are working on and that makes it very hard for us to pick up. So I think there’s some little things you can do, some strategic things you can do to kind of reduce that mental load of task switching.

Brett McKay: So if this is your dissatisfaction profile, there’s actually a lot of things you can do with your current job to maybe remedy. You can talk to your boss about the distractions or the multiple roles and maybe you can reduce some of that but it might reach a point where it’s just expected that you do these multiple roles and you realize you’re not gonna be able to do the work that you want to do, well. That might nudge you to look for another job.

Tessa West: Yeah, I think one thing that happens a lot is organizations talk out of both sides of their mouth. They say that they’re really good at promoting people internally into leadership positions, but at the same time they ask everyone to do all the things at once and they’re not very strategic about how they get you to prioritize roles and then they kind of like shift the narrative on you like, well the reason why you weren’t promoted is because you weren’t good at prioritizing your work. What they don’t realize is that maybe the middle manager is asking 15 people to do all of these different jobs at once. And so if your own leader manager can’t help you with that task of just prioritizing your roles most important to least important and they keep telling you that there’s a tie between one and two and five and six, then that’s probably a red flag that they don’t even know, what this should look like. And they’re not even sure about people who’ve been successfully promoted and how they prioritize their own roles. So, you can make that list and go out into the world and talk to hiring managers with your role prioritization and during interviews ask them point blank how are you gonna help me stick to kind of this rank ordering of roles when people start nudging me to do additional work. Like what process do you have in place to sort of protect me to insulate me from that role creepage that a lot of us are feeling at work. And I think that’s a fair question to ask.

Brett McKay: And as you were talking it reminded me it might be useful too if you’re feeling stretched too thin to do a broader view of the, your career landscape. ‘Cause you might find, Okay, I’m feeling stretched too thin at this particular company or organization. Maybe if I just go somewhere else and keep the same career, you might find the same problem because industry-wide, they’re asking these people who have this career to do multiple roles no matter where you go. So you might have to do some more investigation like talk to your friend who lives in Nebraska or different states. Are you seeing the same sort of thing in your career? Like if you’re a teacher, are they having you do this, this, this, this? And if it’s like, Yes, and it’s like well maybe this is all over the place, maybe I have to go to a different career.

Tessa West: Yeah, absolutely. And I think, some people can handle that sort of milling things at once. Some people are really good at boundaries. Others are yes people and they’re people pleasers and if you are a people pleaser and you have a hard time saying no or you care a lot about your team liking you, then you know your achilles heel at work is gonna be taking on the extra work of people taking on those extra roles. And another kind of interesting thing I learned when writing this book is that a lot of times when we are taking on extra work of people, it’s not because there’s a free writer problem in our teams where people are just sort of offloading. Often this happens in well structured teams that don’t have a free writer problem where people are actually getting credit for their work. What they don’t realize is when you get credit for doing something someone else is paid to do, even if people verbally recognize it, it’s very hard to kind of integrate that information into a promotion decision. Rarely will a boss say, Yeah, this person was amazing, they took on the work of everybody else on the team. I think we should promote them because it makes them look like a bad boss. It makes them look disorganized. And so doing work that someone else is technically paid for, even if you get credit for it in the moment, rarely translates to an actual promotion opportunity. And I think people don’t understand that disconnect. That is pretty common.

Brett McKay: Okay. So the next reason, the fourth reason that people might be unhappy with their job is they feel like they can’t get ahead in their career because they never get promoted or get a raise. They’re just overlooked all the time. I mean you call this the runner-up. Why are some people consistently runner-ups in their career?

Tessa West: There’s a couple sort of really difficult answers to that question. The first one is that they have less status than they think they do. And this is a hard pill to swallow, this idea that maybe people don’t respect you, admire you, they don’t care about your contributions as much as they need to in order for you to get promoted. And I asked people, were you given an explicit reason why you weren’t promoted and most weren’t, but they had some kind of sense that low status might be at play. I asked people who make promotion decisions why people weren’t get promoted. They kind of said the same thing, no one was really told they don’t have status, but that’s kind of the reason that’s… It’s implied but never actually said. And then among those who successfully get promoted, they’re like, Oh yeah, absolutely. It’s because I was told that I have status. So the only people who are actually sure that status matters are those who are successfully promoted. ‘Cause it’s easy to tell someone when they have status. It’s very hard to tell them when they don’t. And I talk a lot about in my book of like how to read status, which is this kind of complex topic around things like if you write an email to the boss, how quickly does the boss reply versus if someone else does, is it quicker or slower? Status is often conveyed very indirectly through these subtle ways. When you contribute to a meeting, does your contribution stick?

Do people build on it or do they always switch topics? And this kind of like soft nebulous construct is one of the main reasons why people keep going up for promotions and not succeeding because they don’t have as much status as they think they have and they don’t, they’re never told that and they have a really hard time correcting for that. So I think, that’s kind of one of the trickier things that you have to learn about yourself. One of the more kind of threatening, stressful ones, some of the kind of more obvious ones are things like you’ve missed a couple key roles along the way. So you’ve got maybe a battlefield promotion. You were hired into a position of leadership that you really didn’t have the experience for, but you missed one or two things in the past. And whoever’s making decisions now really cares about those one or two things. And they can even feel a little bit arbitrary, but they’re gonna die on this hill of we’re not promoting someone without those things. I think those are a couple things. And then there’s the like scary not within your own hands problem. Like, my boss actually doesn’t have enough status to promote me. My boss loves me, but when that person walks into the room, no one listens to who they think should get promoted because they’re not a big enough deal. They don’t have enough tenure at this company. So those are the three main categories of reasons I found that people really struggle.

Brett McKay: Okay. So you have to become more status savvy if this is your problem and you talk about again like status, you said it’s very subtle. You have to pay attention to how people respond to you, how quickly they respond to you, to emails, et cetera. Because you don’t want to ask, Hey, do I have status? Do you guys think I have high status? ‘Cause everyone’s like, what the heck, you weirdo? You don’t ask that question.

Tessa West: Yeah, I know it’s a totally weird question. Yeah.

Brett McKay: But you can ask a question to your boss or maybe your coworkers like, do you think my contributions have an impact? And if the answer’s no, hopefully they’ll give you that honest feedback.

Tessa West: You’re even smaller than that. Say you bring three ideas to a meeting and none of the ideas stick, and they don’t end up being any of the ideas written on the whiteboard. You can talk to your boss or your team members and say, can you maybe give me some insight into why you think those ideas weren’t the ones we went with, or in what ways it was presenting these ideas maybe not ideal. So the smaller, the more specific and behavioral you can get and the kind of the more immediate after the thing, the better. And I think a lot of people in client-facing jobs have this problem where they don’t know why clients don’t prefer them. They prefer someone else over them. And they walk out of that client meeting and think, I thought that went really well. And then they find out, okay, well we got the job but the client doesn’t ever wanna talk to you again. And they don’t… No one really explains to them why that was the case. And it could be something like they interrupted too often or they talked for too long or they were too loud. It could be little things like that that accumulate over time that if you don’t get corrected, you just end up kind of hitting your head against a wall constantly ’cause you can’t move forward.

Brett McKay: So what are some solutions, you mentioned just asking for feedback, figuring out like what you need to do to advance in your job. Let’s say you do those things. How do you make sure your contributions get recognized?

Tessa West: I think that you need to do a lot of work ahead of time to figure out whose voices get heard and why. Kind of one of the more fascinating findings from my work on status is that, it’s not always the person who makes the most persuasive argument. It’s the person who organizes the team ahead of time and says things like, let’s all go around the room and share one idea. And so people have some instincts of what gives them status, and those instincts are talk a lot, come with the most persuasive arguments and interrupt people, those are dominance things. Those aren’t actual prestige things. And so you kind of need to learn how to figure out where your expertise lies, stay in your lane with that expertise and minimize the amount of jocking you do for status in groups.

Nothing loses status quicker than trying to take it from another person in the actual meeting by verbally dominating that person. That is a losing strategy that I see people try over and over again. It’s a very heavy hand in strategy. You gotta kind of do your work behind the scenes, and that includes kind of networking with other high status people who aren’t in your role, so you know who you need to actually impress, who actually matters in this meeting. And so subtle things, subtle leadership behaviors that actually show you care more about the team than the individual is a huge way to gain status. I did a lot of work, a lot of research looking at what’s called a status jolt in the workplace. So this happens when all of a sudden we have our team, we know who has status, we know who doesn’t, and then something happens to the organization to kind of throw a wrench in it, a merger, or we’re now all on Zoom or whatever the thing is.

The people who try to cling to their old status with selfish behavior, by trying to outperform others, not sharing information, not being helpful, they lose their status the quickest. And so clinging to old status is also a way you can lose status in a new team. You need to actually be pretty helpful and not so Machiavellian if you want to actually gain status after jolt like that. So focus more kind of on helping behavior and on transparency around process and around kind of soft leadership. Those are the best ways to actually gain status at work, not by being heavy-handed and loud and interrupting people or even being the most persuasive in the room.

Brett McKay: Let’s say you do all this stuff, you try to do a better job of managing your status at your current job, but you do it and nothing’s coming from, you’re still getting overlooked. So I think it can happen ’cause you’re kind of, people kind of put you in a box. It’s like, well this is Bill. Bill is just this way, even though…

Tessa West: Yep. We know Bill.

Brett McKay: We know Bill, but like even though Bill’s been doing some great stuff, some great moves to make contributions, it’s like well, it’s Bill, he’s just not gonna get a promotion. When do you realize like I’ve reached my limit here. Like people aren’t gonna give me a promotion. Like how do you decide I gotta jump ship?

Tessa West: I love that question. It’s like, at what point is your status, your old status so stuck to you that impression formation change is impossible. Like everyone’s just decided who you are. It’s a bit of like manifest destiny problem. Like you cannot override that impression that people have of you. It’s too difficult. I do think if you’re stuck in that position, and it doesn’t matter what you do, then a learned helplessness is gonna set in and you’re gonna figure out it doesn’t matter if I actually improve here, nobody cares because they are anchoring their judgments on my past behavior. I really do think that’s when you have to consider leaving. If you are getting pretty hard evidence that no matter what you do here, you can never correct for your mistakes of the past. It’s a little like I have cheated on my husband five times, he’s never gonna believe me ever again. Then I think you are kind of stuck.

And we know from the impression formation literature that it’s really hard to override those impressions once we have them of someone. And so I don’t wanna be Pollyannish about this and say you cannot fix your status. You can override those impressions, especially if you’ve been at a place for a while and it becomes kind of impossible, then you might need to actually make a career change. And when you do that, you might have to take a step down before you can take a step up again. You might have to eat a little slice of humble pie to kind of make a move up. You might have to downgrade a bit in order to do that somewhere else.

Brett McKay: All right, so the final one is the underappreciated star. This is someone who’s underpaid and undervalued, compared to what they bring to the workplace. How do you know if you’re an underappreciated star?

Tessa West: I think the kind of first thing that you need to question is, are you actually a star? And I give people a few things you can do to figure out if you have a skill that you are both the best at and is rare at work and both need to be true. If you’re really good at something that everybody can do, then you’re probably not a star. And then the under-appreciation part also takes a little bit of interrogating. So I think most underappreciated stars are told they’re great, but they’re not shown that they’re great in any kind of compensation way that they care about. And it doesn’t have to be money, it can be other perks, whatever the thing is. It’s a lot of promising future compensation. And we see this in small organizations and new startups that don’t have a lot of money or resources to give out. They will bring in a star and they will promise them the world if they just stick around long enough. So if you’re getting a lot of these kind of hypothetical future promises, I’ve worked for organizations that weren’t publicly traded but they promised me stock once they were in which they made up a number to estimate what that number would look like. Those kinds of things tend to be the forms of under-appreciation that people who are at the top of their game experience.

Brett McKay: One factor that contributes to people becoming under-appreciated stars I thought was really incisive is that many companies and organizations are just looking for good enough when hiring. Tell us about this finding.

Tessa West: Yeah, I’m a little cynical about the whole star business, partly because I think most companies don’t actually want a whole bunch of stars. They might not even be able to afford one star. I think a lot of people who are really, really good are in the 99th percentile. They get compensated exponentially more than someone who say the 90th percentile. And so if salaries don’t go up in a linear way, starhood increases. They go up exponentially and it’s often not worth it to pay these stars. And a lot of places who have hired people like this, who have hired so-called geniuses or kind of the more dark version of that as a super chicken that will kind of peck the eyes out of all the other stars to be number one, they find that this is a mistake and that it’s actually better to hire people who are pretty good, who have decent skills, but they don’t have the price tag, they don’t have the expectations of being treated like they’re fancy that come with the true stars, that come with the person who is the CEO at the fortune 100 company or whatever. And I think you need to figure out whether there’s even a market for your starhood. And most places, they can’t afford you and they’re not actually that interested in bringing someone in who is so, so much more powerful than everybody else. There’s a psychological distance that you’ll create should you come to that place.

Brett McKay: Yeah, I imagine this good enough problem is gonna become even worse with the introduction of AI into companies, ’cause like AI can do a lot of the stuff at… It’s starting to be able to do a lot of stuff at white collar jobs. It’s not great, but it’s good enough.

Tessa West: Totally.

Brett McKay: And so companies are like, well instead of paying a human being with all these advanced degrees $100,000 a year to do this job, we’ll just use AI that costs us $20,000 a year.

Tessa West: Oh, absolutely. And I’m seeing this… Any kind of job in psychology where you’re hired as like a consultant to kind of import and export knowledge from science and make it palatable to the masses. So go summarize these 15 academic articles and make a PowerPoint presentation, explaining what growth mindset is. Those people used to make like one 150K, coming out with a PhD in psychology. Now, they make 0K because AI chatbot GPT can do that in five seconds. It’s a little janky. Sure. But someone can take five minutes to kind of make it pretty, add the human touch to it. And so there are just these whole white collar careers that are just being rapidly shrunk, and anyone who used to kind of be good at summarizing things, no longer has a job. And I do think we’re seeing kind of more and more of this good enough problem. Even cropping up a pretty sophisticated levels like coding and things like that, which we used to just really rely on well-trained computer scientists to do, AI does that just as well, if not better.

Brett McKay: Yeah. The thing you have to start thinking about is, well, how can I take that skill that can now be done by AI? How can I take that to the next level, like higher level? What can AI not do and maybe AI can’t make those bigger connections? I don’t know, I’m just kind of shooting off the hip here.

Tessa West: Yeah, I could tell you the jobs AI can’t do that people are really desperate for is anything in hospitality, in healthcare, any human interfacing jobs where you have to actually talk to people. So not like back office jobs where you can chat with your Bank of America app or whatever, but anything that involves like a complex human interaction of any form. And whether that means making a salad or talking to a client or giving someone a shot in the arm, those are the jobs that people are really distrustful of AI. Even like ironically, things that AI could be better at, like radiology and reading scans, there’s a complete distrust. I have a paper on like the trust of this kind of machine stuff. There’s a distrust when there’s no human eyes on it. And so ironically, even some of these things that AI is getting better at, people still wanna hire people for as kind of the last stop. And I think anything like that, if you’re a new career person listening to this, human interfacing stuff where people wanna talk to another human being, those are the jobs you need to start looking into.

Brett McKay: Well, Tessa, this has been a great conversation. Where can people go to learn more about the book and your work?

Tessa West: So you can go to tessawestauthor.com to take the quizzes from Job Therapy and from Jerks at Work as well. If you wanna read about my research, you can go to tessawestlab.com.

Brett McKay: Fantastic. Well, Tessa West, thanks for your time. It’s been a pleasure.

Tessa West: Thank you so much.

Brett McKay: My guest today was Dr. Tessa West. She’s the author of the book, Job Therapy. It’s available on amazon.com and at bookstores everywhere. You find more information about her work at her website, tessawestauthor.com. Also, check out our show notes at aom.is/jobtherapy, where you can find links to resources, where we delve deeper into this topic.

Well, that wraps up another edition of the AOM podcast. Make sure to check out our website at artofmanliness.com, where you can find our podcast archives, as well as thousands of articles that we’ve written over the years about pretty much anything you can think of. And if you’ve done so already, I’d appreciate you to take one minute to give us a review on apple podcast or Spotify, it helps out a lot. And if you’ve done that already, thank you. Please consider sharing the show with a friend or a family member you think will get something out of it. As always, thank you for the continued support. Until next time, it’s Brett McKay reminding you to listen to the AOM podcast, and put what you’ve heard into action.

This article was originally published on The Art of Manliness.

Businesses and individuals often feel overwhelmed and stretched — that they can’t get done all the work they need to. The solution they frequently turn to is finding a new app to use or hiring more employees to spread the load.

But my guest would say that you can steal back hours of productive time simply by using the tools and teams you have now, if you learn to use them in a more efficient way.

Nick Sonnenberg is the founder and CEO of Leverage, an efficiency consulting business and the author of Come Up for Air: How Teams Can Leverage Systems and Tools to Stop Drowning in Work. Today on the show, Nick explains how people spend almost 60% of their time doing work about work, and why hiring more people can actually make the problem worse rather than better. He then shares his “CPR Business Efficiency Framework,” and how making changes in how you communicate, plan, and manage resources can open up hours of time. We talk about how to organize your communication channels so your work day isn’t taken up by what Nick calls “The Scavenger Hunt,” one of the most underutilized tools for taming your inbox, how to stop wasting time on meetings, and tiny changes that will add up to many hours saved each year. Along the way, we talk about how some of these tactics can save you time in your personal life as well.

Resources Related to the Podcast

This article was originally published on The Art of Manliness.