Ryan Holiday's Blog, page 2

June 18, 2025

38 (Or So) Lessons On The Way To 38

There is something melancholic about birthdays. I’m not the first to notice this. Another year has gone by, a wise man once said, and we can’t help but note how little we’ve grown. “No matter how desperate we are that someday a better self will emerge,” he said, “with each flicker of the candles on the cake, we know it’s not to be, that for the rest of our sad, wretched pathetic lives…this is who we are to the bitter end…..inevitably, irrevocably. Happy birthday? No such thing.”

Marcus Aurelius?

Not quite, although ​Jerry Seinfeld is now a Marcus Aurelius fan​, I am happy to report.

I’ve always loved that scene from Seinfeld (which happens when George tells Jerry to stop being his funny self). I’ve related to it on some birthdays but on others, like today, I don’t. I find I have grown quite a bit during most of my trips around the sun, to the point where I hardly recognize the person who first started these posts a decade ago (you can see my birthday posts for ​26​, ​27​, ​28​, ​29​, ​30​, ​31​, ​32, ​​33​, ​34​, ​35​, ​36​, and ​37​ here). I feel like I have changed a lot in the last year and that a better self has and is emerging.

Anyway, as always, here are 38 things I’ve learned in 38 years.

– I put up my first website a few days after I graduated from high school and I’ve been writing more or less every day since. It hit me recently that that means I’ve been doing this for two decades. And you know what? I’m just starting to feel like I’m getting the hang of it. If you told me twenty years ago that that’s how long real confidence would take, I don’t know if I could have handled it.

– This reminds me of an old Zen story. A student approaches a master: How long will it take? Ten years, he says. What if I work really hard? the student asks. Fifteen years, the teacher says. No, you don’t understand, the student says, I am in a hurry. Ok, then, the teacher replies, twenty years. Mastery is not something you can rush. Nor can you rush the opportunities you think you need. When I look back, that’s one thing I am struck by, how lucky I am that most of my biggest opportunities came later. If I had gotten them when I thought I wanted them, you know what would have happened? I would have blown them because I wasn’t ready.

– I’ve been a runner a long time and as I’ve talked about before, the one thing you get asked all the time as a runner is “Are you training for a marathon?” My answer has always been, “No, this is the marathon.” That is, the day-to-dayness, the doing it for no reason other than because, is the real challenge I’m tackling.

– Along those lines…I love the phrase from the college basketball coach Buzz Williams, be an every day guy. “You have to be Every Day,” he says. “There’s no, ‘We’ll do it tomorrow.’ No. We’re doing it today…You gotta do it every day. And if you can’t do it every day, then you’re going to struggle because it is every day.” I try to be an every day writer. An every day runner. ​An every day father​. An every day spouse.

– Anyway, the last couple of months I have been training a little—I want to do the 26 miles from Marathon to Athens this summer. I haven’t done it yet, so I can’t be certain about anything, but I will say after looking at a lot of the training regimes, I haven’t had to change much. Which was my point all along: ​If you stay ready, you don’t have to get ready​.

– A couple of years ago, my wife suggested I read this book called Fair Play by Eve Rodsky. It’s a great book and will definitely improve your marriage. The funny thing is I think the concept of mental load is equally essential in the workplace. If I give someone a task, I should be able to give them effectively all of it—meaning I shouldn’t have to worry about it or them, they should be updating and keeping me informed, if they run into problems they should come to me with the solutions etc. People who can manage themselves go far in life. People who can’t go nowhere.

– Again, it’s always shocking (and humbling) to discover just how hard it is to get good at something. I’ve been doing ​The Daily Stoic Podcast​ since 2018 and ​the long-form interviews since 2020​. We’ve done hundreds of millions of downloads and it did well from the jump—so I think I can say people have always liked it—and yet I had a feeling doing an interview last week (approximately my 550th) that I was just getting the hang of it. But you know what? That sensation—that feeling of really being on the inside of something, finally, the clicking that happens after all that work? There is really nothing like it.

– Why am I rushing my kids? I’m rushing them (and me) where exactly? To the end of their childhood…precisely the thing I will soon enough miss desperately. What will I do with this time I am trying to save, what will I do with this time I get to myself after they go to bed? Watch Netflix?

​Rich’​ is how much you see your kids, I’ve been saying at Daily Dad. ​Power’​ is how much say you have over your own schedule.

-When I lived in New York, someone told me, “The thing you have to understand about New York is that things just cost what they cost.” This reminds me of Seneca’s famous line about “​paying the taxes of life, gladly​.” Things cost what they cost–travel costs delays, fame costs critics, kids cost noise, etc etc–and the sooner you learn to pay these taxes gladly, the happier you will be.

​You are what you won’t do for money​. Your priorities and principles are demonstrated by what you say no to.

– I had the excruciating experience last year of updating The Obstacle is the Way for the 10th anniversary edition​. Honestly, I would not wish re-reading (​especially into a microphone for an audiobook​) a book you wrote in your twenties on anyone. And again, that’s a book that has been loved by millions of people! ​There was so much I had to fix​. So much I have gotten better at.

-That being said, if I envy anything about that younger version of myself, it’s that I didn’t have much of the self-consciousness I have now. I was freer. Things were simpler. I didn’t know what I didn’t know. I didn’t have the taste to properly judge or understand what I was doing. There is something to be said for that.

– There’s a line in The Great Gatsby where Jay asks Nick Carraway if he’d like to do a little job for him, a way to make some money on the side. Nick declines and says later, that had he answered differently, perhaps the whole course of his life might have been different. When I look at some of the people I used to work for or knew and I see where they ended up, I often think of how had I made even a few different decisions, I could have ended up on a very different trajectory.

– By very different, I mean very different. For instance, it occurs to me now that I was probably being vetted for something by Peter Thiel (I too had written a memoir he’d liked…). ​I could have gone to Washington in 2017​. I’d like to think I was always just a little too independent to get fully sucked into anyone’s orbit. But maybe I just got lucky. The point is: Each of our choices adds up to who we are going to turn out to be.

– I am very ambitious as a writer. I no longer have any ambitions as an author. ​I’m not aiming at lists. I don’t think about deals. I rarely even look at sales numbers​. I have stopped tracking how other people’s books are doing. What I’m saying is that I have locked into process and tuned out publishing. The funny thing is that my results have gotten better the more I have flipped this ratio. I have also gotten much more content.

​The people who are most successful in life, who accomplish the most, who dominate their professions—they don’t care that much about winning​. They are obsessed, instead, with improving at the thing they love doing.

– Most labels are unhelpful, too—filmmaker, writer, investor, entrepreneur, executive. These are nouns. But what gets someone to that position? Verbs. Forget the nouns. Focus on the verbs.

– I don’t know what AI will mean or do over the long term. What I can say is that I have gotten a lot out of it. I mean that practically (for instance, it’s helped me fill out graphics and illustrations ​in my talks​ and ​in the Daily Stoic videos​), but I also mean personally. As in, in figuring out how to use a new technology, I feel invigorated and improved. ​I’ve read books about it​. ​Listened to podcasts about it​. We talk about it in our weekly staff meetings. I’ve taught my kids about it. It is good to figure new things out. It is good to be a beginner at something again.

– You know what AI isn’t going to replace? Actually, what it will necessitate even more? A good bullshit detector. It may well turn out that the most valuable thing a person can have in this new era is a broad liberal arts education and a strong dose of common sense.

– As I waited at my gate at the airport for an extra hour or so the other day, it occurred to me: This is what anxiety steals from you. Or rather, this is what we steal from ourselves when we are anxious. I could have been at home with my kids, but I had let the remote possibility of traffic override my ability to do that. It occurs to me this is true not just for time, but for the present moments it takes from me and for the conflict it sucks me into. ​Anxiety is expensive.

– Related…​I had an incredible conversation with Dr. Becky Kennedy​ that every parent—or really just any human—needs to listen to​. (If you haven’t read her book, ​Good Inside​​, yet…what are you doing?!). ​In the episode​, she defined anxiety as “some amount of uncertainty coupled with our underestimation of our ability to cope.” It reminded me of what Marcus Aurelius writes in Meditations: “Consider all that you’ve gone through, all that you’ve survived.” If these last five years haven’t given you a sense of your ability to cope…I don’t know what will.

– The less news I consume, the more informed I seem to get. “Read not the Times,” Thoreau wrote. “Read the Eternities.” Read old books. Read philosophy. Read history. Read biographies. Study psychology. Study the patterns of history. Read ​​The Great Influenza​​ to be informed about pandemics. Read ​​All The King’s Men​ and ​It Can’t Happen Hereto be informed about the demagogues of this moment. Read The Moviegoer to understand your listless teenager. Read The Years of Lyndon Johnson to study power and ambition. ​Read the Stoics​. And definitely, definitely, definitely, read ​Zweig’s biography of Montaigne​ (​which I talk about here​).

– I’m not sure I’ve ever opened a social media app and then after logging off thought, “Wow, I’m so glad I did that.”

– Conversely, I have never taken a walk without thinking, after, “I am so glad I did that.”

– I am always glad I jumped in the water. Even when—perhaps especially when—it’s really, really cold.

– It’s also rare that I have regretted asking for help. Sure, sometimes it can be more trouble than it’s worth, but at least I got some practice doing a thing that’s hard–being vulnerable, putting myself out there, connecting with someone.

– At least once a week, someone asks us if we’re going to open a second location of ​the bookstore​. And at least three struggling bookstores have reached out about us acquiring them. The answer is usually a polite “no.” Sometimes it’s “Are you insane?” “Do Not Go Past The Mark You Aimed For” is one of the most important laws in The 48 Laws of Power. Know when you’ve won. Know what enough is. Know your limits.

– A couple of months ago I was working on something in a car from JFK to Manhattan. The car bounced and the Sharpie I was using made a little mark on the door. It was stupid for me to have been using a permanent marker in a moving car, but obviously, the driver didn’t see and I could have just gotten away with it. It was weird how much I had to work myself up in my head to tell the driver when I got out. “If you have to charge me for it, I understand,” I said. It was an uncomfortable little conversation, but I’m glad I had it. I honestly don’t even know if they ended up charging my card for anything, but if they did it was worth it. Calling fouls on yourself is not fun, but it’s a habit you need to build.

– A day or two ​before my ill-fated talk at the Naval Academy in April​, as I was weighing whether I was going to speak up about the book bannings on campus in my remarks, I emailed someone who I really admire. They are a USNA graduate and someone who has served their country for many years with quiet, honorable leadership. I said, hey, I’m thinking about saying something but I don’t want to cause trouble for anyone and I definitely don’t want to get a good person fired (especially if they end up replaced by someone worse.) This is what they wrote back:

“I think you should just speak directly about what you truly believe. That is always a path.”

– I will say, in these deranged times we live in, one thing I have continually taken solace and inspiration from is when smart people or people whose work I respect, take a little time out of their day to say “Hey, I’m not OK with what’s happening,” or use their platform to reiterate basic values like decency, honesty, justice or kindness. Maybe this doesn’t feel like much to them or to you, but we are social creatures. We look around us, we look above and below us and we make our choices based on what we see other people doing. Deciding to stay silent breeds silence and complicity. ​Speaking up breeds courage and virtue​.

– After a flight into LAX and a long drive to Palm Springs, I finally got my family into our hotel room. Then I started changing to go for a run. Are you out of your mind, my wife said. It was 4pm and 104 degrees out. “That’s not self-discipline,” she said, “that’s self-harm.” She’s probably right. It’s a fine line…and sometimes my problem is too much discipline, not too little.

– Something I’ve started saying all the time to employees: “Let’s start the clock on this.” If the bindery says it’ll take six weeks to make another run of the ​leatherbound Daily Stoic, I want to “start the clock” as soon as possible. I don’t want to add days or weeks by being indecisive, procrastinating, or slow to process an invoice. We don’t control how long others take, but we do control whether we waste time on our end. The project will take six months? Start the clock. You’re going to need a reply from someone else? Start the clock (send the email). Getting the two quotes from vendors will take a while? Start the clock (request it). It’s going to take 40 years for your retirement accounts to compound with enough interest to retire? Start the clock (by making the deposits). It’s going to take 10,000 hours to master something? Start the clock (by doing the work and the study).

– Whenever I go and do something with my kids (like a trip or an activity or an errand) I try to tell myself: Success is wanting to do this again. That is to say, it’s not about accomplishing anything or checking off certain boxes—did we see all the sights, did we get what we needed to get, did we arrive on time or whatever—it’s ultimately whether we got along well enough, enjoyed the experience enough, that at some point in the future they’ll say: “Hey, remember when we went to that concert? Can we do that again?” or “Oh, you’re driving across town to grab that thing? Can I come?”

– For a long time, my writing habit was all-or-nothing—either I wrote a lot of words or I didn’t. Over time, I’ve lowered the stakes: now the question is simply, “Did I make a positive contribution to my writing today?” Sometimes that means writing, sometimes editing, adding, deleting. Sometimes I’m home and it’s in my office, sometimes I’m on the road and it’s on a plane or in a hotel room. Sometimes it’s a big contribution, sometimes it’s a little contribution. The line from Zeno was that big things are realized by small steps. That’s what I try to remind myself: every day, just make a positive contribution.

– It’s important to realize that most of the time people are not playing three-dimensional chess. Most of the time they are slaves to their emotions and impulses. Most of the time they have no idea what they’re doing at all. I’ve been amazed at the degree to which smart people I know manage to convince themselves that what they’re seeing is part of some thought-out plan and thus rationalize what is obviously insane or explain away what would be otherwise deeply alarming. We forget ​Hanlon’s Razor​ at our peril.

– When we were working on ​​​What You’re Made For​​​, George Raveling—who I think is one of the most remarkable people of the 20th century—said that when he wakes up in the morning, as he puts his feet on the floor but before he stands up, he says to himself, “George, you’ve got two choices today. You can be happy or very happy. Which will it be?” (Voltaire put it another way I love: The most important decision you make is to be in a good mood.)

– The basic most essential of responsibilities: Do not let assholes turn you into an asshole. To not let the cruelty harden you, to not let stupidity make you bitter, to not let outrage pull you down to its level, to not let the sonsofbitches turn me into a sonuvabitch. It is a timeless struggle, as Zweig put it in 1942 about Montaigne in 1562, saying that we must “remain human in an inhuman time.”

– Remember, you don’t die once at the end of your life. You are dying every second that passes. We are going in one direction. Don’t rush through it. Don’t miss it. Have something to show for it.

I feel very lucky not just to be 38 but to be here at 38. I have been blessed in so many ways. I have been able to live so much. I’m good. If I get to do another one of these a year from now, I’ll be grateful, but it will be a bonus.

I spoke at a biohacking conference a few weeks ago where the stated purpose was all about living well into your hundreds. I teased them a little. Why? I said. So you can spend more time on your phone? So you can accumulate more stuff? So you can check more boxes off your to-do list? It’s not like these were researchers trying to cure cancer or engineers trying to bring clean water to communities that don’t have it, or scientists trying to solve the climate crisis—people whose services the world desperately needs…yet we all think we need to, deserve to, live forever.

I hope I get a lot more time with my kids and my spouse and my work, I do. But I also understand that I’ve gotten a lot of time on this already—and that too much of it I wasted or didn’t appreciate in the moment.

These 38 years have been good to me, better perhaps than could be reasonably expected. I think I’ve used them well. I hope you do, too.

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Published on June 18, 2025 12:33

June 4, 2025

You Are What You Won’t Do For Money

—Today’s newsletter is sponsored by Shortform.

It was a sales pitch, so I take it with a grain of salt, but according to an email I got a few weeks ago, I have a seven-figure opportunity sitting in front of me.

And I’m apparently too stupid or closed-minded to see it. 

All I would have to do is partner with a supplement maker and produce a line of supplements connected to the Daily Stoic brand—marketing their ability to help with “calm, clarity, and resilience”—and I could very easily make several million dollars. They’d handle everything: procurement, production, design, fulfillment. I’d just have to lend my brand and my platform to do it. 

The only problem? I don’t want to. 

I’m not exactly opposed to supplements or vitamins. I actually take a few each morning. I even advertise some on the Daily Dad and Daily Stoic podcasts. Nor am I opposed to making money. I don’t think there is anything wrong with it, and neither did the Stoics (“No one has condemned wisdom to poverty,” Seneca writes in On The Happy Life. “The philosopher shall have considerable wealth, but it will not have been pried from any man’s hands, and it will not be stained with another man’s blood.”)

But I have always declined to do things like Daily Stoic T-shirts and hats and cheap merch: It doesn’t feel right. It doesn’t get me excited. It doesn’t seem like a responsible use of my platform. 

So as long as I’m in charge, it won’t be. 

I remain a proud capitalist. I have built companies and invested in many others over the years. I make and sell a lot of things for Daily Stoic. But I like the things we make. I believe in them. They were things I wanted to create for my own personal use or that I thought addressed a real need—that they worked commercially was extra. (Nor do I pressure anyone about them. If you don’t like it…don’t buy it! That’s the other part of capitalism when it works well: It is a voluntary exchange.)

I understand that there is a certain privilege in my attitude, which is why I do my best not to judge people in different financial circumstances. At the same time, I have come to believe that we are defined by the things we don’t do for money. 

Do you know who Audie Murphy is? He’s the most decorated soldier in American history. Before he turned 21, he fought in nine campaigns, was wounded three times, and received 33 medals for valor—including the Medal of Honor, three Purple Hearts, and every combat decoration the Army offers. Once, against an onslaught of 250 German soldiers and six tanks, Murphy ordered his men to fall back to safety—alone, he climbed into a burning tank destroyer and used its single machine gun to hold off the Nazis for over an hour, single-handedly killing 50 of them, refusing to give an inch of ground, holding the woods until reinforcements came. (Read his memoir, To Hell and Back…it’s incredible.)

After the war, he became an actor and a musician. In 1968, he did another courageous deed: he turned down enormous sums of money to appear in a series of cigarette and alcohol commercials. “How would it look: ‘War Hero Drinks Booze’?” he said. “I couldn’t do that to the kids.”

I was also struck by Harry Truman’s ability to rise up through the corrupt Kansas City political machine without being corrupted. “In all this long career, I had certain rules I followed, win, lose or draw,” Truman explained. “I refused to handle any political money in any way whatever. I engaged in no private interest whatever that could be helped by local, state or national governments. I refused presents, hotel accommodations or trips which were paid for by private parties…I made no speeches for money or expenses while I was in the Senate. I lived on the salary I was legally entitled to and considered that I was employed by the taxpayers, and the people of my country, state and nation.” I was even more struck by his post-presidency years because they stand in such contrast to the practice today: Truman was nearly broke after leaving office. In fact, the reason there is a presidential pension is because people were concerned about a destitute former president! Yet for Truman, this outcome was vastly preferred to compromising his principles. 

In Right Thing, Right Now, I tell the story of Martha Graham, who was approached in 1935 with the opportunity of a lifetime: an invitation to present her work at the upcoming Olympics. It was a chance to dance on the world stage, the kind of opportunity that no talented or ambitious person could afford to turn down.

​​Yet there she was, turning it down.

“Three-quarters of my group are Jewish,” she told the emissaries from Berlin. “Do you think that I would go to a country where they treat hundreds of thousands of their coreligionists with the brutality and cruelty that you have shown Jews?” Shocked that self-interest hadn’t worked—that she wouldn’t look the other way like so many others—the Nazis tried a different tactic. “If you don’t come,” they warned, “everyone will know about it and that will be bad for you.”

But Graham knew precisely the opposite was true. “If I don’t come,” she said, “everyone will know why I didn’t and that will be bad for you.” She may have been a starving artist well into her forties and could have used the money and exposure, but it wasn’t worth her integrity. It wasn’t worth her soul. By acting on her principles, she struck a public blow against an evil not enough people had yet condemned. 

Back in April, I told this story on stage at the global gathering of the Entrepreneur’s Organization. Everyone broke out in applause at Graham’s line, but as they say–and as Graham would have experienced–you can’t live on gratitude or respect. It must have been a hard choice. It must have been a scary choice. It was the right thing to do as a person…but it didn’t change the fact that she still had her financial obligations as a businesswoman with dancers to support.

Every entrepreneur knows that struggle. You have your views…and you also have payroll to meet. Or investors to satisfy. Or your ego to fill…

It’s the scene in The Great Gatsby where Gatsby approaches the young Nick Carraway, the cousin of Daisy Buchanan, the love of Gatsby’s life. Ultimately hoping to win back Daisy, Gatsby tries to first win over Carraway. “I carry on a little business on the side, a sort of sideline,” Gatsby tells him. “And I thought that if you don’t make very much…this would interest you. It wouldn’t take up much of your time and you might pick up a nice bit of money. It happens to be a rather confidential thing.”

It’s only later that Nick, understanding more clearly that Gatsby was a gangster and a bootlegger, comes to see that “under different circumstances that conversation might have been one of the crises of my life.” Gatsby was trying to draw him in, hoping to hook him on the money and the lifestyle. 

I have not always been good at this and I have gotten myself into some fixes that might have gone badly for me. I sometimes look back at clients and people I worked for in my twenties—and even later—and I feel the urge to take a shower. Growing up, I suspect I heard my parents talk more about financial success than about integrity or ethics. It took time for me to develop both the character and the confidence to be better able to say “NO” to things that gave me the ick or that seemed iffy. 

I wrestle with it still. I turned down a talk last year from an organization I thought was a scam. I weighed whether I should cancel another one recently with someone whose politics I find abhorrent.  

My reading has helped me get better at this. Perhaps because my inclination was to make money, I found it particularly impressive when people turned down an opportunity to make money. Especially when those people really needed it. Especially when it was a lot of money.  

Imagine if you had been offered one of those enormous greenwashing contracts from LIV, a Saudi-backed rival league. Ditching the PGA (and trying to bully their old league into letting them keep their privileges in the process) wasn’t technically illegal. But it was definitely pretty gross.

Rory McIlroy turned down hundreds of millions of easy dollars because he believed that the new league was bad for the game. That where his money comes from matters. That his choices don’t just reflect his own values and priorities, they shape those of the many young players, the future generation of golfers, who look up to him. And that a decision “you make in your life purely for money,” he explained, “doesn’t usually end up going the right way.”

(And by the way, what was his reward for this? His game took a major hit from the distraction and the PGA hung him out to dry!)

But that can be how it goes. 

Do you know what they called Truman when he was elected to the Senate? The colleagues who didn’t snub him as a hick referred to him as the “Senator from Pendergast”—implying that he was bought and purchased, in the pocket of Tom Pendergast, the all-powerful Kansas City boss. Truman, who had forgone millions in bribes and deals, still got stuck with a reputation for being corrupt! 

If you’re making the right decision because you want to be rewarded reputationally, you’re probably going to be disappointed. 

Even though I feel like I’ve made some expensive decisions about what I won’t do in my career—as well as some expensive decisions in how we do what we do (I talk about our manufacturing and import decisions here)—I still have to put up with people accusing me of “$toicism” or being a grifter or whatever. There are plenty of people who dislike the coins we make or the courses we have done—or even the fact that I write books! I turn down all sorts of lucrative ads—from gambling sites and alcohol companies and THC companies and crypto—and still, the comments sections on our videos and the podcast are filled with complaints about advertisers. I’m sure someone will respond to this very email with a disagreement about whoever sponsored it. 

That’s something Marcus Aurelius talks about in Meditations—the frustrating experience of “earning a bad reputation by good deeds.” It can even be more galling than that. Someone else will do some kind of Stoic supplement at some point! They’ll probably make a bunch of money from it. 

That person will just not be me. 

You can’t call it a principle, as the expression goes, unless it has cost you something—money, access, friends, followers, convenience, an opportunity to get ahead. 

You shouldn’t call yourself rich unless your hands are clean.

It’s not really your platform unless you decide what goes on it. 

You’re not free if you can’t say no.

And you don’t know who you are unless you know what you won’t do for money.

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Published on June 04, 2025 12:58

May 21, 2025

This Is Something I’ve Turned To Over and Over Again When The World Seems Dark

But first…​Join me live in conversation with my friend and mentor, George Raveling, on May 29th at The Painted Porch Bookshop​! George is one of the most remarkable people of the 20th century. He became the first African American basketball coach in what’s now the Pac-12 and went on to have a Hall of Fame career. He was instrumental in bringing Michael Jordan to Nike and has mentored some of the most influential coaches in college basketball. You do not want to miss this event. ​Get tickets here​!

I guess I could try to put into words how much I love this book.

I could try to explain how this 84-year-old book about an obscure 16th-century philosopher is uniquely relevant to our times.

Or I could just tell you I put my money where my mouth is:

I bought 1,000 copies of this book.

Literally.

As in, all the available stock…which I was only able to get after I had my agent connect me with the publisher, Pushkin Press, who I then begged to print one final run before it went out of print.

1,000 copies of Montaigne at The Painted Porch

That is how much I loved ​this little Stefan Zweig biography of Montaigne​.

Zweig—who is best known for his haunting book The World of Yesterday, about Europe and the era destroyed by WWI—wrote Montaigne while on the run from the Nazis. It would be the last thing he published before despair killed him.

Surprisingly, for such a well-read man, Zweig was not familiar with the works of Montaigne until he was in his late fifties. In the cellar of a bungalow in Petrópolis, Brazil—living in exile after the Nazis condemned him, as they had all the Jews, banned his work, and burned his books in the streets —he chanced upon a “dusty old edition” of ​Montaigne’s essays​. “Certain authors reveal themselves to us only at a certain age and in chosen moments,” Zweig would write of the man who found him at his lowest ebb.

I myself, read Montaigne’s work when I was in my mid-twenties, but I did not read ​this biography​ for the first time until 2016 (Montaigne lived through divisive political times). I read it again in 2020 (Montaigne lived through the plague). I read it again about a year and a half ago (Montaigne lived through religious wars, technological disruption, economic instability, and a kind of mass hysteria Zweig would refer to as “the herd’s rampancy”).

It’s a very surreal experience to read a book about a man turning inward amidst the cruelty and close-mindedness of his time, written some 350 years later by a man fleeing the brutality and persecutions of his time…as modern society continues to experience (and inflict) the same horrors on itself.

“It seemed to our generation that Montaigne was simply rattling chains we thought long since broken,” Zweig writes, “and we could never imagine that in fact Fate had reforged them for us, far stronger and crueller than ever before. It is precisely a generation like ours, cast by fate into the cataract of the world’s turmoil, to whom the freedom and consistency of his thought conveys the most precious aid.”

Montaigne’s was an epoch defined by fear, persecution, demagogues, rabble-rousers, civil strife, and the unraveling of long-standing institutions. It was a time of revolutionary movements. It was a time of new ideas. It was a time of technological disruption. It was a time of destabilization and conflict. The church, which had long been a unifying force, was for the first time becoming a source of bitter division. The recently invented printing press didn’t just spread knowledge and ideas but also misinformation, outrage, and hatred. “Instead of humanism,” as Zweig put it, “it was intolerance that spread.”

It was only a few decades earlier that Michelangelo had painted the Sistine Chapel. Magellan had circumnavigated the globe. Copernicus had displaced the earth from the center of the universe. The Renaissance had flowered, bringing with it beautiful art and earth-​shattering awakenings. Scientific breakthroughs reshaped the world and what seemed possible. A new continent had been discovered across the Atlantic. Trade boomed. Wealth spread.

“But always when the wave climbs too high and too quickly,” Zweig tells us, “it falls more violently, like a cataract. And just as, in our time, the miracles of technology have morphed into the most horrific elements of destruction, so elements of the Renaissance and humanism which at first seemed to offer salvation proved a lethal poison.”

Yet for all the darkness shrouding the book, it remains an incredibly consoling and, I think, hopeful, book.

Because Montaigne did the impossible. He pulled up what Zweig describes as one of the toughest tasks in the world, “maintain[ing] one’s intellectual and moral independence and preserve it unsullied through a mass cataclysm.”

How did Montaigne pull it off? How was he not ​made crazy by the craziness around him​? How did he not let the sonsofbitches turn him into a sonuvabitch? How did he, as Zweig put it, “remain human in an inhuman time”?

The answer is a lot of work.

It began with his incredible and totally unique education as a young man (which I am so fascinated by, it is a full third of my next book, Wisdom Takes Work. You can preorder that ​here​—we have some signed copies that we will certainly run out of by the time it comes out in the fall, so be sure to grab it now).

​Preorder my next book here​.

From his earliest days, Montaigne was exposed to people who were not like him. Despite his great wealth, his parents made sure he was raised amongst the common people—people they believed their son could grow up and help (and certainly never feel superior to). Later, he would strike a coin for himself to carry as a reminder. “I reserve judgment,” it said.

In a time still partly medieval, he was a lover of books. Oh how he loved books.

Perhaps no one in any epoch read, studied, and conversed with the past more than Montaigne. “Books are my kingdom,” he said. “And here I seek to reign as absolute lord.” His library, thousands of books, was a temple of wisdom. “He wanders about the room,” another biographer describes, “taking from his shelves one book after another, opening them at random, reading a scrap, and then talking about it.”

On the shelves was his copy of Terence from school. There were the Stoics. There was Lucretius, Horace, Virgil, and Diogenes Laertius. There was his beloved Plutarch. When he wasn’t home? “I never travel without books, neither in peace nor in war,” he’d say. “Books are, I find, the best provisions a man can take with him on life’s journey.”

But all this reading did not make him smug or certain. No, it made him humble and open-minded. That was his famous saying, the one that motivated him to invent the essay, or, in French, an attempt: “Que sais-je?” What do I know? In the form of rambling meditations—some no more than a page, some almost the length of a short book—Montaigne would try to find out, what did he really, truly know?

And although he’s famous for that line, his ceiling was inscribed with ones he liked better, that showed the key to his genius.

From the Greek philosopher, Sextus Empiricus, ΟΥ ΚΑΤΑΛΑΜΒΑΝΩ (I do not understand), ΕΠΕΧΩ (I stop), and ΣΚΕΠΤΟΜΑΙ (I examine). From Terence, “I am a man and nothing human is foreign to me.” From Socrates, “Impiety follows pride like a dog.” From Pliny, “The only certainty is that nothing is certain.”

Montaigne was aghast at the way people treated each other, especially people they disagreed with. He believed that ideas should be questioned and that humans were prone to error. “It is to take one’s conjectures rather seriously,” he would say, “to roast someone alive for them.” Yet that’s literally what people were doing–burning their religious opponents to death over disagreements that could never be proven.

When the New World was discovered—basically in his lifetime—he did not think that the people who lived there were savages. No, from his reading of Herodotus, he understood that every distant land has its own culture and beliefs—and that our customs would seem just as barbaric to them. In one of his best essays, On the Cannibals, he writes at length about what he learned from his extensive reading and his many conversations with a French explorer who had lived among the so-called cannibals for over ten years. He was fascinated by their relationship to nature, how they trusted in its abundance and saw no need to try to alter or dominate it. He was fascinated by how they lived without all the systems and structures that define European society—no money, no written language, no math, no government, no social hierarchy, no private property, no formal economy. He was fascinated by their core values—“two things only: bravery before their enemies and love for their wives.”

And he was fascinated by the ritual meaning behind their most shocking custom, how cannibalism was, for them, “not as something done for food—as the Scythians used to do in antiquity—but to symbolize ultimate revenge.” He wasn’t defending or excusing the “horrible barbarity” of cannibalism. What struck him was that “while judging correctly of their wrong-doings we should so blind to our own.” Did the cannibals draw and quarter each other? Did they commit mass murder and atrocities? Accuse each other of black magic? Who was actually more barbaric?

Most of all, Montaigne understood what it was like to be an other. As new‐money merchants, the Montaigne family was not fully accepted by the aristocracy. Montaigne’s mother’s side of the family were Marranos, Spanish Jews who during the Inquisition converted to Christianity under the threat of death. In the Inquisition, multiple relatives of Montaigne had been burned to death, including a great‐great‐great‐grandfather. And then on the other side, his paternal uncles were Protestant.

He didn’t fit in with anyone and so he tried to be sympathetic to everyone. He tried to be open minded about everything. Because he knew where the absence of this led. This moderation, this tolerance, did not win him the friends it should have. He sensed that he was a man without a country. He knew he had a target on his back. “I was belabored from every quarter,” Montaigne lamented; “to the Ghibelline I was a Guelph, to the Guelph, a Ghibelline.”

I’ve said before that what I love so much about the Zweig biography is how timely it is. While reading this book, it’s hard to not see alarming warning signs about today’s world and how it’s verging on becoming like Montaigne’s and Zweig’s. The same forces that haunted their eras—intolerance, extremism, misinformation, institutional decay, fanaticism and fundamentalism, technological disruption, demagogues, charlatans, and con artists—are once again reasserting themselves all around us, eroding trust, stirring division, and making it a challenge to be sane, rational, informed, decent humans.

But what I also love about the Zweig biography is that it also gives us solutions: Turn inward. Master yourself. Take your education into your own hands. Do “not fall for every smooth talker,” as Marcus Aurelius would say. Read, study, and converse with “the rich souls of times past,” as Montaigne said, for “history,” Zweig added, “is [the] great instruction manual.”

This is why I started giving ​Zweig’s little book on Montaigne​ to people in chosen moments—in 2016, during the pandemic, before and after the recent election. It’s why I pick up my copy and reread it whenever I need or want to step back and get a little distance from the craziness of our epoch. And it’s why I bought those 1,000 copies—because I wanted to continue to be able to rave about it and never run out of stock at the bookstore.

Because Montaigne really is a man for our times…

A wise and insightful thinker who never took himself too seriously.

A man obsessed with figuring himself out: why he thought the way he did, how he could find happiness, his fetishes, his near-death experiences.

A man who lived in a time of dysfunction and coped by looking inward.

A man who devoted his life to the work of wisdom, the work of living the philosophical life, of living those ​four virtues​.

We’re lucky that he did, and we must do the same. We must take from his example the need to be always curious, always questioning, always ready to learn something new.

Montaigne kept learning until the day he died, and indeed, the questions he devoted his life to, the inner journey he relentlessly applied himself to, continues on through each of us today.

We must be brave and disciplined enough to pick up the task he laid before us. The task of remaining human in an inhuman world. Of thinking clearly and independently. Of mastering ourselves in a world where so much conspires to try to pull us into being part of the mob and rabble. Of, in short, becoming wise.

It takes study. It takes reflection. It takes experience. It takes humility.

It is a battle to be won over ego, over ignorance, over the self, over the mob, over “the vortex of pandemonium,” Zweig said, and “the deranged prejudices of others.”

Most of all, it takes work.

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Published on May 21, 2025 12:40

May 7, 2025

These Are All The Ways I Feel Poorer Than I Am

Financially, I’m doing pretty well.

My books sell more than you’d think books about ancient philosophy would sell (​actually, you can preorder the new one here​)…and it turns out that ​starting a bookstore in a small town in rural Texas​ was not actually the dumbest business idea in the world.

I was lucky to have a decent ten years in marketing before I became a full-time author, and I made some good investments along the way. I’ve saved and I try to live within my means.

So when I say that when I look at my life, I feel poorer than I’d like to be, I don’t mean I’m not doing well. This would be insulting to the single mothers out there, the people crippled by medical debt and to the underclasses that the modern economy exploits.

The reason I am thinking about this at all comes after a conversation I had with Sahil Bloom, who has a new book about the different types of wealth, on the Daily Stoic podcast (​you can listen to the episode here​ or watch it on YouTube). Along with financial wealth, there is time wealth, he says. And social wealth. And mental wealth. And physical wealth.

He’s right.

I’ve met some billionaires that I would have no trouble describing as poor—not just because they had an endless desire for more (​which was Seneca’s definition​), but because their lives were a mess, because they were preposterously insecure, because they were estranged from their families, because they had few friends, because they didn’t take care of themselves.

I don’t say this to judge; after all, I started this very piece by alluding to the fact that I’m not as rich as I’d like to be in a few areas.

For instance, as I’ve said before, I feel like—despite my net worth and career success—I am far too anxious and stressed out. Not so much about the state of the world, but about things needing to go well.

I often get nervous when I fly. Not because we might crash, but what if we’re delayed and I miss the talk I am supposed to be giving? Or what if I’m delayed and my schedule gets messed up and I fall behind? Objectively, this is silly! I would be fine financially if I had to cancel something or if events conspired to prevent it from happening. I am way ahead of my deadlines and am perfectly able to absorb some setbacks. Yet here I am, acting like I’m on the razor’s edge.

Anxiety, I’ve come to realize, is a very expensive habit. It has cost me so much. A lot of misery, a lot of frustration, countless hours of sleep. It’s caused me to miss out on a lot of things that are important to me. How many family dinners have I ruined by letting my mind wander to what could go wrong? How many minutes of vacations have I missed out on because I was preoccupied, lost in spirals about things that hadn’t happened? How many opportunities have I passed up because I was too caught up in my own fears? How many nights did I waste lying awake at night, worrying about what might or might not happen?

The tragedy of anxiety is that it feeds on itself. Like the ancient symbol of the snake devouring its own tail, anxiety consumes resources that could be used to discard it.

​I carry this reminder with me​—a medallion engraved with Epictetus’ phrase, ta eph’hemin, ta ouk eph’hemin (“What is up to us, what is not up to us”). On the back is a quote from Seneca: “He who suffers before it is necessary suffers more than is necessary.”

It creates real problems from its obsession with imaginary ones. When you have fears that you might run out of money or luck or you feel like your career could end, it affects how you organize your life and your finances. You leave hours earlier for the airport than you need to, only to sit at the gate. You ruminate on the past or the future at the expense of the project you could be working on. You stress about money so much that you don’t put it to use in ways that would make your life less stressful. My wife and I, as we repeatedly try to remind each other, should not be living the way we are. That is to say, we have too much on our plates and not enough people helping us. We’re doing too well financially to feel so anxious, so stressed out, so compelled to do and put up with certain things.

When you live this way, it doesn’t matter your income—you are spending down your capital. You are depleting the accounts of your relationships and of your own happiness.

I am not as busy as some people I know, but I am too busy. Just this week, I was trying to put a doctor’s appointment in my calendar and found I could not. Some people can’t afford to go to the doctor, but some of us, for very different reasons, apparently can’t ‘afford’ it either. I would have to cancel something or miss out on something.

If you’re too busy to take care of your health…can you really say you’re doing well?

I know I would be better off if I had more friends. That’s one of the downsides of success, too. Not only can it isolate you and alienate you from others—this thing we call ‘fame’ is weird, especially if you are already introverted—it makes you a little suspicious. It makes you a little guarded. It makes you a little more inclined to stay in the privacy of your home or office. But mostly what success does is suck up your time. As my friend Austin Kleon has said, “work, family, scene—pick two.” I love my family and I love my work. That doesn’t leave as much time for friends. And he and I talked about that very thing last time we hung out: Why don’t we do this more? Of course, we both know why. It’s a shame…and it’s a privileged impoverishment.

It’s weird to think that as a kid, when I had no money, I would just go over to a friend’s house and just hang out. Nothing scheduled. We didn’t even have anything to do, but we’d spend hours together. It’s weird to think back and be jealous of that kid…but I am. He had something I don’t have any more.

I love where I live, this little ranch we have outside Austin. It was a huge swing, financially, when we bought it. Getting the mortgage almost didn’t happen–banks weren’t exactly lining up to lend money to a self-employed writer at the beginning of his career, trying to buy farm land. We managed to get it and it’s one of the best things we’ve ever done.

We’re tucked away from the noise, the distractions, the rush of the city. We live off an unpaved road. It’s pitch black at night…we’re surrounded by thousands of trees. I look out over a lake, filled with fish and ducks and turtles. We raise cows and donkeys. I can hunt deer and hogs. I love just standing there in the evening and watching the Texas sunset settle over the ranch.

But you know what? I don’t spend enough time at it…or rather, on it. I used to do most of the repairs myself. My wife and I would go out and feed the cows every day I delivered the hay each week. I checked the fences after a storm. Not so much anymore. Partly, because we got the place in pretty good and self-sustaining shape—that was the systems-thinkers in us. We also bought out a neighbor and instead of dragging away the mobile home that sits in a corner of that property, found a wonderful family that we rent it out to in exchange for help with all those chores.

It’s a relief, for sure, but you know what? I miss it. Weeks go by sometimes, and I realize I have not walked more than a few paces from our house (our family walks are usually on our road). It makes me think of one of the most moving and insightful passages in John Graves’ classic book Goodbye to a River,

“A rooting, poking, dog-trailed child turning over stones in a creek bed, or a broke old man wandering back from a pulp mill in Oregon to toe-nudge rusty cans and the shards of crocks at the spot where his father’s homestead once stood, or a drifter in a boat on a river, can all own it right from under you if you don’t watch out. Can own it in a real way, own it with an eye and brain and heart…”

If all I’m doing is looking at it from the back window, do I really own it? Do I really need to own it?

I guess what I am saying is that when I think about a “rich life”—to borrow a phrase from my friend Ramit Sethi—I don’t think that much about money. Actually, that’s my point: Isn’t that the point of having money? To not have to think about it? It’s a life where you feel good, where you feel secure, where you think about what you want to think about.

I remember earlier in my writing career, a time when I would take pretty much every opportunity to do an interview for any newspaper or magazine or podcast or radio show, I got an email one evening to appear live on a radio show the next morning. As I started to reply that I would do it, I thought, I have to change my whole day around tomorrow for this. Which was not unusual—I often reluctantly moved things around for these kinds of things. What was unusual was the next thought, which was, I don’t have to do this. Even if the appearance somehow led to 10,000 extra book sales, it wasn’t going to change my life in any meaningful way. So why not just keep the day I already planned? That moment of realization—that I could say no—changed my life more than any amount of money ever had.

That’s a step towards the life I want.

There are people with enormous fortunes who don’t have that freedom. It’s like that scene at the beginning of Billions where he says, What’s the point of having ‘fuck you money’ if you never say ‘fuck you’? That’s too rude, obviously, so what about just, No thanks. Or, Not right now.

We talk about this in ​the Daily Stoic Wealth Challenge​. You might think Seneca was the richest of the Stoics, but in fact, he is our model of “The Poorest Stoic” throughout the challenge. He was under the thumb of money and ambition and power and status—the things that attracted him to Nero’s service. In thirteen years working for a man who was clearly deranged and evil, Seneca became one of Rome’s richest men, something he paid a tremendous price for. “Many people,” Seneca himself would write, “have riches just as we say that we ‘have a fever,’ when really the fever has us.” The fever had Seneca, trapping him in a gilded cage he eventually realized he couldn’t buy his way out of.

Epictetus, by contrast, clawed his way out of slavery, but was actually far richer and far more free than Seneca and the other ‘rich’ and ‘powerful’ men and women of the time who who had been acquired and ruled by Nero, by ambition, by money, by desire, by fame, by their jobs, their insecurities, their possessions. There’s a great story I love about Epictetus being robbed of a prized lamp, but he shrugs it off because he doesn’t care that much about material possessions. He was able to live just as happily without them. “Wealth consists not in having great possessions,” he said, “but in having few wants.”

About a year ago, I was working in my office above the bookstore and called my wife to see what she was up to. “Hey,” she said, “the kids and I are at the park.” “Oh,” I said, “I’ll just come over there.” And I got up from my desk in the middle of the work day and walked over to play with them at the park.

I can do that because of financial reasons. I can do that because of lifestyle logistics reasons, because we chose to live in this little town. I can do that because my wife and kids want to be around me and I want to be around them. I can do that because, fortunately, I’m in decent physical shape. I can do that if I do the work on myself and remember that I don’t have to be stressed about this or that deadline.

And as I walked over to the park, it hit me,

Oh, this is what I work for.

How lucky am I? How great is this?

I could be a billionaire and not be able to do this.

Now if I could just stay in that state of mind more of the time, well, I’d really be doing well.

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Published on May 07, 2025 11:57

April 30, 2025

This Is How Smart People Get Smart (And Fools Get More Foolish)

In the fall of 1961, Commander James Stockdale began a course at Stanford he had eagerly anticipated on Marxist theory. “We read no criticisms of Marxism,” he recounted later, “only primary sources. All year we read the works of Marx and Lenin.”

It might seem unusual that the Navy would send a 36-year-old fighter pilot to get a master’s degree in the humanities, but Stockdale knew why he was there. Writing home to his parents that year, he reminded them of a lesson they had instilled in him, “You really can’t do well competing against something you don’t understand as well as something you can.”

At the time, Marxism was not just an abstract academic subject, but the ideological foundation of America’s greatest geopolitical enemy. The stakes were high—the Soviets pushed a vision of global communism and the conflict in Vietnam was already flashing hot, the North Vietnamese fueled by a ruthless mix of dogma and revolutionary zeal. ‘Marxism’ was, like today, also a culture-war boogeyman used by politicians and demagogues.

Just a few short years after completing his studies—September 1965—Stockdale was shot down over Thanh Hóa in North Vietnam, and as he parachuted into what he knew would be imprisonment and possibly death, his mind turned to the philosophy of Epictetus, which he had been introduced to by a professor at Stanford.

The North Vietnamese had many prisons and prison camps, but the Hỏa Lò Prison was famously the worst. Hỏa Lò means “fiery furnace” or “Hell’s hole,” which is what it was—a dark dungeon where captives were physically and mentally tortured to the unimaginable extreme. Stockdale would spend the next seven years in Hỏa Lò—or the “Hanoi Hilton,” as his fellow inmates would come to call it—in various states of solitary confinement and brutal torture.

His captors—sensing perhaps that he held terrible secrets, including having flown in the Tonkin Gulf the night of the so-called “incident”—sought desperately to break him. Stockdale famously drew on ​the Stoicism of Epictetus​, but he also leveraged his knowledge of the practices and the mindset of his oppressors.

“In Hanoi, I understood more about Marxist theory than my interrogator did,” Stockdale explained. “I was able to say to that interrogator, ‘That’s not what Lenin said; you’re a deviationist.’”

This was a story I intended to tell the midshipmen at the U.S Navy Academy a couple of weeks ago, where Stockdale, as a graduate of the class of 1947 and Medal of Honor winner, is revered. For the last four years, ​I’ve been delivering a series of lectures on the cardinal virtues of Stoicism​ and was scheduled to continue on April 14th with a talk to the entire sophomore class on the theme of wisdom.

But roughly an hour before my talk was to begin, in my hotel room getting ready, I received a call—Would I be willing to refrain from any mention in my remarks of the recent removal of 381 supposedly controversial books from the Nimitz library on campus? My slides had been sent up the chain of command at the school, who was now, as they explained, extremely worried about reprisals from the Secretary of Defense or appearing to openly flout Executive Order 14151 (an anti-DEI order.)

When I declined, my invitation—as well as a planned speech before the Navy Football team, with whom my books on Stoicism are popular—was revoked.

In his writings and speeches after his return from the Hanoi Hilton, Stockdale often referred to what he called “extortion environments” to describe his experience in prison. He and his fellow POWs were pressured to comply with demands—answering simple questions, performing seemingly innocuous tasks, appearing in propaganda videos, confessing to war crimes—under the threat that if they declined, there would be consequences.

No one at the Naval Academy intimated any consequences for me, of course, but it was extortionary all the same—I had to choose between my message (to say nothing of my rights as a private citizen) or my continued access and welcome at an institution that has been one of the honors of my life to be associated with.

As an author, I believe deeply in the power of books. As a bookstore owner in Texas, ​I have spoken up about book banning many times​ already. In fact, when they tried to remove certain books from the high school library in our town, my wife and I partnered ​with Scribd to give out hundreds of copies of them to local residents​. That’s why the window of our store currently features this quote from one of my favorite Rage Against the Machine songs:

But setting all of that aside, even if I had no previous connection to this issue, I had been invited to the Naval Academy to deliver an address on the virtue of wisdom. How could I not mention what had gone on just a few hundred yards away?

As I explained repeatedly to my hosts, I had no interest in embarrassing anyone or discussing politics directly (although they had had no issue with ​the talk I gave at this very lecture series entirely about Jimmy Carter​, another Academy graduate, one year earlier). Nor did I want to cause trouble or put someone’s job at risk. I did, however, feel it was essential to make the point that the pursuit of wisdom is impossible without engaging with (and challenging) uncomfortable ideas.

​Seneca​, another Stoic philosopher, used a military metaphor to make this very argument. We ought to read critically and dangerously, he said, “like a spy in the enemy’s camp.” This is what Stockdale was doing when he studied Marxism on the Navy’s dime. It is what Seneca was doing when he read and liberally quoted from Epicurus, the head of a rival philosophical school.

The current administration is by no means unique in its desire to suppress ideas it doesn’t like or thinks dangerous. As I intended to explain to the midshipmen, there was considerable political pressure in the 1950s over what books were carried in the libraries of federal installations. When asked if he would ban communist books from American embassies, however, Eisenhower resisted.

“Generally speaking,” he told a reporter from the New York Herald Tribune at a press conference shortly after his inauguration, “my idea is that censorship and hiding solves nothing…” He explained that he wished more Americans had read Hitler and Stalin in the years previous because it might have helped anticipate the oncoming threats. “Now, gentlemen,” he concluded, “…let’s educate ourselves if we are going to run a free government.”

The men and women at the Naval Academy will go on to lead combat missions, to command aircraft carriers, to pilot nuclear-armed submarines, and run enormous organizations. We will soon entrust them with incredible responsibilities and power. But we fear they’ll be hoodwinked or brainwashed by certain books?

It is good that Mein Kampf was not one of the books removed from the Naval Academy library…but this makes the fact that ​Maya Angelou​ was, all the more inexplicable. Whatever one thinks of DEI, we are not talking about the writings of external enemies here, but ​in many cases, art, serious scholarship and legitimate criticism of America’s past​. One of the books is about black soldiers in WWII, another is about the memorialization of the Holocaust. Another was written by ​a person I had interviewed on the Daily Stoic podcast​, and had been interviewed by a week earlier! No one at any public institution should have to fear losing their job for pushing back on such an obvious over-reach, let alone veterans who have served this country in combat, yet here we are.

Indeed, the decision not to protest the original order—which I believe flies in the face of basic academic freedoms and independence—is what put the current leadership in the academy in the now even stickier position of trying to suppress criticism of that decision. “Compromises pile up when you’re in a pressure situation in the hands of a skilled extortionist,” Stockdale reminds us. “You can be had if you make that first compromise, offer to make that ‘deal,’ or ‘meet them halfway.’”

Of course, I write about many of these topics—holding the line, developing competence, having integrity, not compromising—in Right Thing, Right Now. I have not always managed to do this in my own life and career (as I confess to my regret and shame in the Afterword to Courage is Calling). These decisions are not easy nor are they always clear. I very much sympathize with the leadership (in uniform and otherwise) who have been put in this impossible situation. I also know firsthand, it is very difficult to go along with policies that compromise your values without becomingcompromised.

As I say in the preface to each book in the series, the virtues are interrelated and inseparable. Yet, there’s a reason that ​wisdom​ is considered the mother of the virtues. It is wisdom that helps us find what Aristotle called the “golden mean” between two vices. It is wisdom that tells us when to apply courage, the midpoint between cowardice and recklessness. It is wisdom that teaches us how to stand firm and persist when we know we are doing right. And it is wisdom that finds the line between good and evil, right and wrong, fair and unfair, ethical and unethical.

I felt I could not, in good conscience, lecture these future leaders and warriors on the virtues of courage and doing the right thing—as I did in ​2023​ and ​2024​—and then fold when asked not to mention such an egregious and fundamentally anti-wisdom course of action. I could not give a talk on the subject of wisdom and not address a very timeless and unfortunately, very prevalent tendency to get rid of books that we disagree with or think controversial. What good is it to speak about leadership and character in the abstract and avoid the very real challenges in front of us? As our constitutional order and our very laws are being placed under incredible strain—to say nothing of our basic morals and decency.

In many moments, many understandable moments, Commander Stockdale had an opportunity to do the expedient thing as a POW. He could have compromised. He could have obeyed. It would have saved him considerable pain, preventing the injuries that deprived him of full use of his leg for the rest of his life, perhaps even returning him home sooner to his family. He chose not to do that. He rejected the extortionary choice and stood on principle.

For me, with slightly less on the line, to do the expedient thing, it would have been a betrayal not just of Stoicism, the philosophy I have tried to apply in my life, but also a betrayal of Stockdale in whose name I was giving the lecture and whose story I was telling in the talk that I was going to give.

And so there in the hotel after receiving the phone call and having my talk cancelled, I packed up and headed to the airport. On my flight home, I decided I wasn’t going to go quietly. In line with the idea that the obstacle is the way, ​I was going to try to use this​. Mid-flight, I took out my computer and wrote ​a piece that ended up running in The New York Times and getting picked up by many other outlets and publications (​CNN​, ​The Free Press​, ​The Preamble​, ​ABC​, ​Yahoo News​, and more).

After finishing the draft and turning the slides I had prepared over in my mind, I thought, they can prevent me from going on stage but they can’t prevent me from delivering the talk. So in my studio in Texas where we record The Daily Stoic Podcast, ​I gave the talk that I was going to give at the Naval Academy​. It was obviously a slightly different environment—no stage, no slides on a projection screen behind me, no live audience—but it is more or less the talk that I would have given to those midshipmen.

“The greatest educational fallacy,” ​Stockdale would write​, “is that you can get it without stress.” The road to wisdom, to living the philosophical life, living by those four virtues, leads through a long path of stress and toil and struggle.

It takes work, as I put in the title of the ​new book​.

It is the work of our life.

Stockdale’s example—forged by his liberal education at two of America’s best institutes of higher learning—stands there for all of us to follow in matters big and small.

​My new book is officially available for preorder​.

For the last six years, I’ve been working on The Stoic Virtues Series. And now, the fourth and final book—Wisdom Takes Work—is complete.

I wrote this book because wisdom—true wisdom—is the commitment of a lifetime. It is a battle to be won over ego, over ignorance, over the self. It takes study, it takes reflection, it takes experience. Most of all, it takes work. I hope you’ll do that work with me. The book comes out in the fall, but you can preorder it today.

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Published on April 30, 2025 13:24

April 16, 2025

These Are Leadership Ideas I Try To Apply Every Day

Coach Pete Carroll has said that another disappointing season with the New England Patriots���some 15 years into his career���it struck him that he didn���t actually have a coaching philosophy. He was mostly winging it.

Inspired by John Wooden���s ���Pyramid of Success��� philosophy, Carroll got to work filing binders with notes, compiling, defining, and codifying what would become known as his ���Win Forever��� philosophy���the winning actions and mindsets he aims to instill in his staff and players. It was a transformative decision: he went on to win two national championships and then a Super Bowl with the Seattle Seahawks.

Now, when Carroll gives talks, he often opens with a simple question: What���s your philosophy? I once asked him about it, and he told me it���s shocking how many people don���t have an answer. There are many CEOs and generals and investors and coaches at the highest levels who reveal, accidentally, that they have just been winging it.

Although I always saw myself as a writer and wanted that to be my life, I found myself running the marketing department of a publicly traded company by 21. I started my own company in 2012, and given how the world works now, few writers can just be writers. We now have a team of roughly 20 employees across ���Daily Stoic��� and ���The Painted Porch���. Which means I���ve had to develop a leadership philosophy to try to get the best out of the people who are part of it. You can’t make every decision for people, so it���s essential to establish the principles and rules by which others make decisions and operate on a day-to-day basis.

While this post isn���t a totally comprehensive breakdown of my philosophy (if you want that, ���check out The Daily Stoic Leadership Challenge���), these are the core tenets���the maxims, rules, and reminders the people who work for me hear most often.

Sense of urgency. At The Daily Stoic offices above The Painted Porch, I hung up a sign that says, ������A Sense of Urgency���.��� It���s something I cribbed from the kitchens of Thomas Keller, the creator of Per Se, one of the best restaurants in the world. A sense of urgency���that���s what a great chef, a great service staff, a great organization has. While in my personal life I ���may need to work on slowing down a bit������I���m a ���sense of urgency��� guy, always have been���I���d say most people could use a little speeding up. A couple of weeks ago, a shipment of books came in on a Friday afternoon. I heard someone on the staff say, ���We���ll unpack those tomorrow.��� I���m glad I heard it because I had to stop them and explain that, unless the books in those boxes were opened and the orders waiting on them were fulfilled (in time for the morning mail pickup on Saturday), they would not even begin traveling in the customer���s direction until Monday afternoon. So what seemed like a little delay until the next morning was really like a 72-hour delay. Every small delay or shortcut has second-, third-, and fourth-order consequences. That���s why it���s important���whether you���re packing boxes, replying to emails, or making big strategic calls���to think a step or two ahead. Don���t procrastinate. Do it now. Do it with urgency.

Slow down���to go faster. Yes, it���s important to have a sense of urgency. But there���s a difference between urgency and rushing, hurrying, going quickly for the sole sake of speed. There is an old Latin expression that I think captures the balance here nicely: Festina Lente, which means, Make haste slowly. A sense of urgency���with a purpose. Energy plus moderation. Measured exertion. Eagerness, with control. It is about getting things done, properly and consistently. They like to say in the military that slow is smooth and smooth is fast.

Start the clock. One of the things I say all the time is ������Have we started the clock on this?������ When someone tells me that it���s going to take six weeks for our bindery to make another run of the leatherbound Daily Stoic, I want to ���start the clock��� as soon as possible. I don���t want to add days or weeks to that process by being indecisive about how many to order or by procrastinating on finalizing the order or by being slow in processing an invoice. We don���t control how long it takes other people to do stuff, but we control whether we waste time, whether we are inefficient on our end���The project is going to take six months? Start the clock. You���re going to need a reply from someone else? Start the clock (by sending the email). It will likely take a while for the bid to come back? Start the clock (by requesting it). It���s going to take 40 years for your retirement accounts to compound with enough interest to retire? Start the clock (by making the deposits). It���s going to take 10,000 hours to master something? Start the clock (by doing the work and the study).

Don���t touch paper twice. That���s a great rule from the productivity guru David Allen. If you look at an email, begin to edit a piece of content, open a text, whatever���complete the task then and there. This has been driving me nuts on a home remodel we���re doing. The amount of decisions that have come to us more than once is insane. Because the contractor forgets things, because it turns out they didn���t give us the right parameters the first time, because they were asking before we were ready. But people do this all the time! They have bad processes that make them do more work than they need to.

What���s taking up a lot of your time? One question I regularly ask my employees���and myself���is: What���s eating your time? Sometimes this is just life but sometimes, it���s unnecessary. On one of our weekly calls not too long ago, I could tell my video producer was feeling overwhelmed. I asked, what���s taking up a lot of your time? Animations. He said it was taking hours to produce just two minutes of animated content for our Daily Stoic videos (which a previous editor had often included in our videos and become part of the style). I like animations���but not that much! So we cut way back on them and everything got better. Unless you want your boss to micromanage you, you can help them by flagging things that if they knew about they would help you fix. (And by the way, AI has now helped us do these animations faster).

Don���t punish people for improvements. Sometimes people are afraid to tell you about inefficiencies or even potential improvements because they are worried it will turn out badly for them. That you���ll get mad. Or you���ll take away responsibilities or find someone else to do it cheaper. I try to reiterate all the time: I not only won���t punish you for this, I will reward you. If you help save us money���by reducing an unnecessary vendor or service���I���ll give you a piece of it. If you find out that something in your role no longer has a positive ROI or isn���t worth doing, we���ll get rid of it and find something different and better for you to do. If you find a way to work faster with AI, I���ll celebrate that. Your job is to make the company better, not to do your ���job��� as it was originally defined.

Make a positive contribution every day. Compound interest is one of the most powerful forces on earth. And you can apply that to your own work. People sometimes ask how I write the Daily Stoic email every morning, which of course, I don���t. I write one or two every day, constantly making small deposits to the bank of emails. Over time, that compounds���we have a Google Doc we call ���UNSENT,��� which, as I type this, is 217 pages long with emails ready to go. Little things add up. The line from Zeno was that big things are realized by small steps. That���s what I try to instill in my team: every day, make a positive contribution. Most of all, I try to show this with my own writing habits.

Be there when they���re losing, not when they���re winning. When we were working on ���������What You���re Made For���������, George Raveling told me that when he got the head coaching job at Washington State, the athletic director told him, ���I���ll always be there when you���re losing,��� he said. ���I���ll never be there when you���re winning.��� I loved that. I find that I talk to my team the most when they���re struggling���when something���s broken, off-track, or unclear���not when everything���s going well. That���s the job: to help people solve problems, to help them get unstuck. If someone needs constant reassurance or regular praise to stay motivated, they usually don���t last long here. I���m reminded of a time I called Dov Charney, founder of American Apparel, about some little success I���d had on some project. He was very busy and frustrated that I���d interrupted, but politely, he said, ���Ryan, you are calling me to tell me that you did your job.���

Don���t repeat the same mistake. On the one hand, I���ve always loved the story of IBM CEO Tom Watson supposedly calling an executive into his office after his venture lost $10 million. The man assumed he was being fired. ���Fired?��� Watson told him, ���Hell, I spent $10 million educating you. I just want to be sure you learned the right lessons.��� But on the other hand, the thing that frustrates me the most���and the only reason I���ve ever fired someone���is when they keep repeating the same mistakes. If you learn from your failures, great. But if you���re just stuck in a loop, not applying the lessons, it���s not going to work.

Why is it being done that way? One day I noticed our team was packing shipments in a pretty inefficient way. I asked why. The answer? That���s how so-and-so showed me when I started. No one had questioned it since. This happens all the time���in businesses, on teams, in life. People inherit a process, follow it out of habit, and never stop to ask: Is this the best way? Does this still make sense? The most useful question in any system is often the simplest: Why are we doing it like this? This is especially important to ask of tasks that eat away at time better spent on something else.

Steal like an artist. (This is also ���a great book we carry��� at The Painted Porch.) At some point, I realized many of our best ideas were inspired by others. ���The book tower���������as I���ve written���, one of the single best marketing and business decisions we made in the whole store���was partly inspired by a cool floor-to-ceiling tower of books about Abraham Lincoln in the museum attached to Ford���s Theater in DC. Some of our top-performing ���reels on Instagram��� were inspired by other creators. So now, at the end of every weekly staff meeting, we go around and share one idea we���ve seen out in the world���on social media, on podcasts, on YouTube, in movies and documentaries, at other small businesses���and talk about how we might do our own version of it. Not copying, but adapting. Remixing. Borrowing what works and making it ours.

I���m leaving this with you. Like a lot of men of my generation, I���ve learned about this concept of ���mental load��� in relationships (the way, unthinkingly, a lot of responsibilities, emotional obligations and tasks are placed on women). My leadership philosophy is that when I give you a task, that���s your task. Your job is to handle it and be in charge of it. If I have to follow up with you, if I have to push you to get started, if I have to check your work, then I may as well have done it myself. If you are coming to me with problems (as opposed to solutions) or, when you are explaining something to me, not explaining your assumptions, you are putting it back on my plate. In a successful working relationship, I should be able to have an idea, go to the right person with it, and after I explain it say, ���I���m leaving it with you.���

Respect boundaries. As a leader, you have to understand that your decisions and actions have consequences for people, not all of which are immediately obvious. But you have to think about that. For example, I sometimes have to reiterate that just because I am emailing late at night or on the weekend doesn���t mean I expect a response right then. And for this reason, I���ve gotten better at scheduling emails. But the broader point is that as a boss you have to realize your actions, however seemingly small, carry weight. You have the power to blow up someone���s day or evening or weekend. Try not to do that. Try to be mindful of other people���s time and headspace.

Kids are not a distraction from your work. They are your work. I bring my kids to the office. I talk about them in meetings. When they���re a fan of the guest, I ���let them pop into podcast recordings and ask questions���. And I encourage others to do the same. If you need to take paternity or maternity leave���take it. If you want to bring your kid to work���bring them. If you have to duck out for a school pickup���go. Especially as a father, I���ve tried to model this. I don���t want to treat my kids like a separate life I live outside of work, and I don���t want the people who work for me to feel like they have to either. Being a parent is not a liability or a distraction������it���s one of the most meaningful things a person can do���. Our policies, our expectations, and our culture should reflect that.

Do things only we can do. Something that���s happened with ���Daily Stoic��� over the years is as it has grown, so has the number of copycats. And so we���re constantly asking, what can only we do? With the bookstore, for example, we���re lucky to have authors constantly passing through to record the podcast. While they���re here, they sign books. ���Sometimes we do live events with them���. Those books, those experiences���you can���t get them anywhere else. ���This has always been good advice���, but with these AI tools making it easier and easier to copy and replicate and reproduce, it���s more important than ever to find and focus on the things only you can do.

Do the hard things first. The novelist Philipp Meyer��� (whose book ���������The Son��������� is an incredible read) ���told me on the Daily Stoic podcast���, ���You have to be very careful about to what (and to whom) you���re giving the best part of your day.��� A corollary to this: the poet and pacifist William Stafford had a great daily rule: ���Do the hard things first.��� Well-intentioned plans fall apart as the day progresses. Our willpower evaporates. The world makes its demands. My assistant knows not to schedule anything before mid-morning because early calls and meetings don���t just take time���they sap the energy I need to do the hard work. I want to give my best self to my most difficult things. And I encourage my team to do the same: protect the early part of the day, guard your energy, and use it on what matters most.

It���s not a principle until it costs you something. There are lots of ways to make money���many of them easier and more lucrative than ���writing about an obscure school of ancient philosophy��� or ���opening a small-town bookstore in the middle of a pandemic���. Of course, it still has to make money, but not being motivated solely by profit gives me a certain freedom: the ability to act with a heart and conscience, to take stands, to say what I think needs to be said. Every time I write something even mildly political in a ���Daily Stoic email���, we lose a disproportionate number of subscribers. I get lots of angry emails. People accuse me of having changed or they say the Stoics would be disappointed. I sometimes remind them���if not ���something about how all of the Stoics were active in politics and explicitly said the philosopher is obligated to participate in politics������that I didn���t build an audience to not write or say what I think. Or when the team alerts me to the number of followers we lost after I said something political on social media, I tell them the same. And besides, how successful are you really if you censor yourself because you���re afraid it will cost you?

Help people get to where they want to go. It���s very unlikely that anyone you hire is being hired for their dream job. They are not signing up for lifetime employment. No, this job is a waystation. I don���t think we should pretend otherwise. ���In fact, we should embrace it���. When Tim Ferriss was looking for someone to run his podcast and email a few years ago, he asked me if he could hire Hristo Vassilev, who was then my research assistant. You know what I said? I said “Of course.” And he’s been Tim’s right hand ever since. Brent Underwood, who started as my intern more than a decade ago at the marketing company I was building, has gone on to write ���a bestselling book��� and build a hugely popular ���YouTube channel���about the ghost town he owns. My last assistant currently runs a large nonprofit. To be clear, I���ve had some assistants and employees that didn���t work out. But I think I’ve got a pretty good “coaching tree” so far. In sports, a coach’s success isn���t just defined by wins and losses, but by their ���coaching tree������the players, coaches, and executives that they discovered and mentored who���ve gone on to do great things in their own careers. It’s a concept I think about a lot and ended up doing a chapter on it in ���Right Thing, Right Now��� because it deserves to be recognized outside of sports. It���s just a wonderful way to measure a life. Your job as a leader is to have a large coaching tree. Almost no one you hire is going to be a lifer. Chances are, you are not offering them their dream job, but you could be the one who helps them get closer to that dream job.

Don’t try to map out the whole game. Along these lines, a few years ago, during our year-end one-on-one, I asked my current researcher, Billy Oppenheimer, where he wanted to go. If you’re still working for me in this capacity in five years, I said, we both screwed up. The way to get the most out of this kind of relationship is if I have some idea of where you want to go. Then I can try to help you get there. He told me he wanted to be a writer but was just waiting to know for certain what I wanted to write about. After he described some complicated way in which he was privately writing stuff and looking for patterns to determine what to write about publicly, I told him, Just start. You���re trying to map out the whole 9 innings. Just throw the first pitch. Soon after, ���he started a great newsletter I read every Sunday���, which led to him now also working for Rick Rubin and signing his first book deal last year.

So yes, it���s critical to define the principles and rules you live and lead by. It���s critical to have an answer to that question, What���s your philosophy?

But as you get to work figuring out yours, keep in mind, you���re better off starting imperfectly than being paralyzed by the delusion of perfection. As they say, another way to spell ���perfectionism��� is p-a-r-a-l-y-s-i-s.

Don���t try to map out the whole game.

Just throw the first pitch.

Just start.

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Published on April 16, 2025 14:11

April 2, 2025

4 Years Of Lessons From Running My Own Bookstore

It was a crazy idea from the start.��

My wife and I were sitting at a cafe in Bastrop, TX and we spotted an empty storefront, a building that���s part of the National Register of Historic Places.

���You know what would be amazing there?��� my wife said. ���A bookstore.���

We started construction the first week of March 2020.��

But somehow, we didn���t lose all our money. It didn���t blow up our marriage. It���s actually been a great experience and, even more surprising, a pretty good business too.��

Four years in, one of the first things people want to know is how our bookstore The Painted Porch is doing, whether it���s a success. I���d say so. I���ve certainly learned a lot along the way, both about business and life, as well as publishing and people and myself.��

Here are some of those lessons:��

Counterprogramming is key. So yeah, opening a physical bookstore in 2020 seemed crazy. Not just to me���everyone said so. Retail was shifting online, books were becoming digital, the pandemic was raging, bookstores were closing���not opening. But that���s exactly why it worked. It was crazy because no one else was doing it. It stands out. It���s different.��

Have more than one way to win. This was a great piece of advice I got from Allison Hill, who owns Vroman���s and Book Soup in Los Angeles: most bookstores only survive if they���re multipurpose spaces. The Painted Porch isn���t just a bookstore���it���s my office, my employees��� office, the place where we record podcasts and film YouTube videos. So if nobody comes in and buys books, we���re not necessarily losing money.�� At the same time, it probably also wouldn���t have made sense to build out this level of podcast studio or even a writing office by itself either. So multi-use allows you to do more than you ordinarily would���across the board.

Resist the pressure to scale. At least once a week, someone asks us if we���re going to open a second location. And at least three struggling bookstores have reached out about us acquiring them. The answer is a polite no. ���Do Not Go Past The Mark You Aimed For��� is one of the most important laws in The 48 Laws of Power. Know when you���ve won. Know what enough is. Know your limits.��

Have a unique proposition. Most bookstores carry thousands of titles. The best one in Austin, BookPeople, stocks over 100,000. We carry about 1,000. It was one of the best decisions we made���both personally and professionally. We only carry books we love. Not only did this make it cheaper and easier to run the bookstore, it makes us stand out. It gives people a reason to come in. If people want a specific book, they go to a certain trillion-dollar e-commerce behemoth. If people want to discover new books and have a unique experience, they come to us. We are the only bookstore in the world with our selection. Again, counterprogramming.��

Create spectacles. Before we opened the store, I was in Bucharest, Romania for a talk. My host took me into a local bookstore that had an enormous globe hanging from the ceiling. I watched as customer after customer came in to take pictures beneath it, before checking out with books. For me, one of the key pieces of the puzzle was figuring out what kind of marquee feature we could add that would make coming to the store an experience. I recalled a particularly cool floor to ceiling tower of books about Abraham Lincoln in the museum attached to Ford���s Theater in DC.��

This inspired our now infamous book tower, which I designed to be built on top of an old, broken fireplace in the building. It���s 20 feet tall and made of some 2,000 books, 4,000 nails, and 40 gallons of glue.

It was not cheap to do. It was not easy to do. It took forever. We had to solve all sorts of logistical problems to make it work. But it���s also probably one of the single best marketing and business decisions we made in the whole store. Invariably, almost every customer that comes in takes a picture of it���plenty more come in because they heard about it and wanted to see it.

Pass it on and pay it forward. I���m proud of the books I���ve championed over the years���of paying forward what inspired me, like the Gregory Hays translation of Meditations (I loved it so much I even put out my own edition). I love looking around The Painted Porch and seeing books you don���t often see in other stores. Just last year, the publisher of Ann Roe���s Pontius Pilate told us they had to do another printing because we���d raved about it too much. Whether you���re a writer, a bookstore owner, a coach, an entrepreneur, a teacher, a parent���when you find something that helps you, inspires you, or moves you���pass it on. Tell people about it. Help others find what helped you..��

Reading will never get old. One of the things that gets me excited about my job is just how much stuff there is that gets me excited���that until recently I didn���t even know existed. I���ve been doing this a long time���reading seriously since high school, obsessed with Greek and Roman history for most of that time. And somehow, I only just discovered Augustus by John Williams? A book that feels like it was written for me���Memoirs of Hadrian is one of my all-time favorites���and I didn���t even know this existed? And it���s not like it���s some obscure old thing���it won the National Book Award! Then just last month I discovered The Last of the Wine, an incredible historical novel that reminded me of everything I loved about Pressfield���s Gates of Fire and Tides of War. That���s what I love about reading: the more you read the more you realize there is much more to read. Even if you have read a lot, there is not just an endless list of great authors and books still to get to, but new ones come out every day! Maybe that���s how you know you���ve found your thing: when there seems to be no end in sight, and that never stops exciting you.

If you���ve always wanted to do it���do it. This has happened to me more than once. When my wife and I moved to a farm, I couldn���t believe how many people said, ���I���ve always wanted to do that.��� Same with opening the bookstore. People hear you have a small-town bookstore and they light up������I���ve always wanted to do that.��� Casey Neistat has a great line: ���The right time is right now.��� If you���ve always wanted to do something, do it. Stop romanticizing it. Stop overthinking it. Try it. Do it small. Do it your way. But do it.

It���s one damn thing after another. My wife suggested opening the bookstore back in the fall of 2019. Then COVID delayed us a year. Then we didn���t feel right opening for another year. Then a freak storm and some political incompetence shut down the power grid���burst pipes, busted roof. Then a global supply chain crisis made books hard to get. There���s the day-to-day stuff too: employees get sick, the internet goes out, shipments arrive damaged, a toilet leaks, the door won���t shut properly all of a sudden. But that���s how it goes. With most things in life, it’s one damn thing after another. Expect it. Work through it. Keep going.

It���s easy to focus on what���s going wrong. In any business or project, it���s easy to fixate on what���s going wrong. As I mentioned, the little daily problems don���t seem to stop. Those things demand your attention, of course. But I���ve found it helpful���even necessary���to make an effort to notice and appreciate the things that are going well, the things that are working, the little wins we get every day.

Don���t overlook simple solutions. There���s a tendency���especially when you care a lot about something���to overthink it. To assume everything has to be big, polished, expensive, professional. But great ideas can be cheap and easy too. One of my favorite bookstores in the world, Gertrude & Alice in Bondi Beach, puts sticky notes inside their books. Just little handwritten notes from employees about why they liked this or that book. No fancy plaques. No expensive signage. We started doing it at The Painted Porch too. It���s fun, it���s human, and customers love it.

Be deliberate with your space. In the book Strip Tees by Kate Flannery (a great guest when she came on the Daily Stoic Podcast���listen to the episode here), there���s a story about Dov Charney walking through an American Apparel store. He stopped, pointed to the tile beneath his feet, and said, ���Do you know how much rent I pay for this tile every day? Do you know how many T-shirts we have to sell just to cover the cost of this one tile?��� I didn���t witness this one���but I saw many performances like that���and now that I own my own shop, the point stuck with me: every inch of space you control is costing you something. Are you using it well? Is it serving the purpose you think it is? In a bookstore���or any business���it pays to be deliberate about what goes where. What are you putting in your most valuable real estate?

Does it make you better or worse? In the middle of the project, when the whole thing seemed impossible and doomed to fail���as we tried to open a bookstore, raise two kids when schools were closed, and make sense of the world���I wrote a note to myself: ���2020 is a test: will it make you a better person or a worse person?��� That was the test that I reminded myself of over and over again: will this make you a better person or a worse person? If starting a business makes you a worse person���if it stresses you out, if it tears your relationships apart, if it makes you bitter or frustrated with people���then it doesn���t matter how much money it makes or external praise it receives. It���s not successful.

A sense of urgency matters. A couple of weeks ago, a shipment of books came in on a Friday afternoon. I heard someone on the staff say, ���We���ll unpack those tomorrow.��� I���m glad I heard it because I had to stop them and explain that, unless the books in those boxes were opened and the orders waiting on them were fulfilled (in time for the morning mail pickup on Saturday), they would not even begin traveling in the customer���s direction until Monday afternoon. So what seemed like a little delay until the next morning was really like a 72-hour delay. Every small delay or shortcut has second-, third-, and fourth-order consequences. That���s why it���s important���whether you���re packing boxes, replying to emails, or making big strategic calls���to think a step or two ahead. Don���t procrastinate. Do it now. Do it with urgency.

Ask why it���s being done that way. One day I noticed our team was packing shipments in a pretty inefficient way. I asked why. The answer? That���s how so-and-so showed me when I started. No one had questioned it since. This happens all the time���in businesses, on teams, in life. People inherit a process, follow it out of habit, and never stop to ask: Is this the best way? Does this still make sense? The most useful question in any system is often the simplest: Why are we doing it like this?

Know the history of your space. I was talking to Jeni Britton Bauer���the founder of Jeni���s Ice Cream���and she told me the first ice cream shops date back to the late 1600s or early 1700s. Her point was that what feels trendy or modern is often something old coming back around. That applies to bookstores, too. Or really any craft or creative business. What you���re doing might feel new or niche, but it probably has deeper roots than you think.

Learn from the cats. When we were thinking about opening a bookstore, I bought a course from a bookstore consultant. I talked to friends. I talked to bookstore owners while on a book tour. I got a lot of advice, gathered best practices, and learned what worked for others. And yet, the single most popular thing about The Painted Porch is something that never came up���the cats. In 2021, we took a family road trip to Cerro Gordo, the ghost town Brent Underwood has been restoring���my kids are obsessed with his YouTube videos���and came home with two cats who have lived at the bookstore ever since. They���re literally the most popular thing about the store. As one Yelp reviewer put it: ���Nice collection of books, clean, very comfy atmosphere, but I���m not going to lie to the great people of Bastrop���I come for the cats.��� Lol. So yes, do your research. Yes, learn from others. But keep in mind, some of the best parts of any project are things you can���t possibly predetermine.

Do things only you can do. Something that���s happened with Daily Stoic over the years is as it has grown, so has the number of copycats. And so we���re constantly asking, what can only we do? With the bookstore, for example, we���re lucky to have authors constantly passing through to record the podcast. While they���re here, they sign books. Sometimes we do live events with them. Those books, those experiences���you can���t get them anywhere else. This has always been good advice, but with these AI tools making it easier and easier to copy and replicate and reproduce, it���s more important than ever to find and focus on the things only you can do.

Zoom out. When we were doing a small construction project at the bookstore recently, we moved an old antique bar and found some paint on the wall, covered in plaster. Carefully scraping it away, we found a date and a kind of sign: January 16, 1922. What was happening in the world that day? Who were the people who stood there and supervised it being painted? What kind of business was in this space a hundred years ago? How many others have come and gone since? It was a humbling reminder: we���re not the first people to try something in this building, and we won���t be the last. It can be very easy on a project to get caught up in the immediacy of what���s in front of you, to get caught up in the day-to-day of running a business or chasing a goal. But every project, every place, every person is part of something much bigger���something that started long before us and will continue long after.

There���s always problems you aren���t even aware of. What started as a small construction project at the bookstore recently led to uncovering another issue, which led us to another thing that needed fixing���and that led to something else entirely. We’re lucky we tackled the initial project. One thing that keeps you up at night is all the things you don’t know are happening. The controversial Samuel Zemurray���s line���per Rich Cohen���s amazing book The Fish That Ate the Whale���was ���Never trust the report.��� He went to South America or Boston or wherever the business was being done and saw the situation up close for himself. He wanted first hand knowledge so as a leader he could make the right decisions.��

I will leave you with one final bonus piece of advice: hard things are good for you. It is only from doing hard things, as the Stoics said, that we learn what we���re capable of. Seneca would say that he actually pitied people who have never experienced challenges. ���You have passed through life without an opponent,��� he said. ���No one can ever know what you are capable of, not even you.���

Opening a bookstore during a global pandemic has been the hardest thing I���ve ever done. It���s been challenging. Expensive. At times overwhelming. There were setbacks we didn���t anticipate, problems we didn���t know existed, and moments where it would���ve been easier to walk away.

Which is what���s made it one of the most interesting, meaningful, and rewarding experiences of my life. We���ve learned so much���about business, about books, about what we are capable of. We���ve built something that matters to our community and to us. And in the end, those are the things that stay with you���not the easy wins, not the shortcuts, not the stuff or the money.

So if you���re thinking of doing something difficult, if you feel called to do something big���do it. Regardless of whether it succeeds or fails, you���ll be better for it. No one will wonder what you were capable of. Not even you.

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Published on April 02, 2025 14:35

March 26, 2025

This Is Something I Am Forever Grateful For

I would never say I am glad it happened.

I don���t want to dismiss the tragedy and the disruption and the loss.

But as I think about what happened five years ago, as I think about my life shutting down for the pandemic in March and April of 2020, I feel an overwhelming sense of gratitude. I see how it changed me. I see what it taught me. I see the trajectory it put me on.

I���m not talking here about the resurgence of Stoicism that came from these last few troubled years, although that too has been fascinating, exhilarating and obviously good for ���business��� as an author. I am mostly just talking about how deeply those strange, quiet months���when I was forced to slow down and stay put���recalibrated what I value, what I prioritize, what I want my life to look like.

In March of 2020, as social distancing and lockdowns started, my wife and two young sons settled into our ranch on the outskirts of Austin. We���d lived there for five years, but we were able to live there in a way we���d never lived there before. No more commutes. No more daily trips to the store. No more weekly trips to the airport. No more waking up in hotel rooms. No more time apart.

We would spend literally hundreds and hundreds of days together���in a row. In a way that I don���t think I had ever spent in one place or with anyone in all my life (my parents having been rather busy people themselves). And never before so free from the mental load���the relentless cycle of logistics, scheduling, planning, packing, and worrying about where I needed to be next���that had always kept some part of me from being fully present.

There is no such thing as parental leave in my line of work. And, like a lot of driven people who work for themselves, I���m not sure if I could have taken time off, that I would have let myself. Instead, I���ve worked constantly for much of my career and much of my young children���s lives, accepting and chasing opportunities���even though that meant many nights in hotel rooms and on airport benches. This, in addition to those ordinary work-from-home days that all writers know, where you are technically home but are, in fact, very far away.

Suddenly, every single day, rain or shine, I was able to take my boys for a long walk in the morning. Most days, we also did their nap in the running stroller or a bike trailer. In the evening, we walked again. We got in the pool together almost every day. We read books. We ate every meal together. I never missed a bathtime or a bedtime.

How many miles did we walk on our dirt roads? How much time did we spend in the woods? How many sunrises and sunsets? How many blackberries did we pick? How many fish did we catch?

Again, I understand that this was privileged���many people had it quite badly, and I���m not just referring to the immuno-compromised. My sister spent the pandemic in a small apartment in Brooklyn. My grandmother spent it in a nursing home. We had friends who were doctors and paramedics, soldiers who were deployed. Plenty of other people still had to work in warehouses, in places and conditions they should have had to���while others lost their livelihood entirely.

So I get that it was privileged. That���s my whole point, I am saying I was incredibly lucky.

I was lucky that I got to see my own home in a new way. One thing that struck us was how beautiful that first spring was���and how new it was. Like, we���d never once, in five years, spent enough days in a row at home that we could actually track spring happening, watching the bare trees go from buds to leaves to a cool, lush forest. We���d missed blackberry season most years. We���d get home after golden hour most days. But now we noticed everything���the small, daily transformations, the subtle shifts of light through the windows, the sounds of birds we���d previously been too busy to even see.

In Chloe Dalton���s lovely new book ���Raising Hare���, Dalton���an ambitious and connected political advisor���finds herself in an old house in the English countryside. On a walk one day she comes across a leveret (a baby wild hare) and nurses it back to life. What ensues is a surreal and moving friendship, as the hare becomes a free-range companion, hopping around the house, snoozing quietly by Dalton���s side as she wrote, running in from the fields when called, drumming softly on her duvet to get her attention, even giving birth and raising babies inside Dalton���s home.

These were not particularly well-known or well-understood animals, in fact, they���re largely ignored. So she had to read not just research papers, but poetry and ancient authors just to find out what they���re supposed to eat. Spending hundreds of lonely, quiet hours with the leveret���which she never named���she learned to understand its habits and needs, seeing the world from its umwelt (to use one of my favorite words) in addition to her own. And she came to see the home and countryside that she lived in differently, too.

���I felt a new spirit of attentiveness to nature,��� she writes, ���no less wonderful for being entirely unoriginal, for as old as it is as a human experience, it was new to me. For many years, the seasons had largely passed by, my perceptions of the steady cycle of nature disrupted by travel and urban life. I had observed nature in broad brushstrokes, in primary colors, at a surface level. I had been most interested in whether it was dry enough to walk, or warm enough to eat outside with friends. I could identify only a handful of birds and trees by name. I hadn���t observed the buds unfurling, the seasonal passage of birds, the unshakeable rituals and rhythms of life in a single field or wood. I now marveled at the purple tinge on the black feathers of a house martin���the smallest creature I had ever seen���which flew into the house one morning���observing the gleam of the sun on the mirror finish of its plumage, before releasing it into the air.���

It���s funny. I spent 2018 and 2019 working on my book ���Stillness is the Key���. One of the main characters of the book is Churchill, whose own relationship with time and the natural world was changed by his love of painting, which he discovered in the midst of a nervous breakdown after WWI. He was introduced to it by his sister-in-law, who, sensing that Churchill was a steaming kettle of stress, handed him a small kit of paints and brushes her young children liked to play with. In a little book titled ���Painting as a Pastime���, Churchill spoke eloquently of the way painting, like all good hobbies, taught the practitioner to be present. ���This heightened sense of observation of Nature,��� he wrote, ���is one of the chief delights that have come to me through trying to paint.��� He had lived for forty years on planet Earth consumed by his work and his ambition, but through painting, his perspective and perception grew much sharper. Forced to slow down to set up his easel, to mix his paints, to wait for them to dry, he saw things he would have previously blown right past.

I was just finishing a very busy book tour for ���Stillness��� when the pandemic hit (I actually crossed through the Venice airport in late January on the day when those two Chinese tourists arrived from Wuhan���later identified as among the earliest COVID cases). I thought I knew what stillness was, but the world was about to teach me about real stillness.

For many of us, the pandemic brought everything to ���a screeching, unprecedented stop. I���t stripped everything down, broke it all apart and made so much of our normal lives���work and personal���unsafe, if not impossible. I wasn���t having to get to this plane. I wasn���t having to battle traffic to get somewhere on time. I wasn���t having to prepare for this talk or that one. There were no meetings, no dinners out, no get-togethers, no pressing deadlines.

For all it took from us, it gave us ���the privilege of an experience out of the ordinary,��� ���as Dalton beautifully put it���.

And yet, what did most of us do with this experience? We complained about it. We resented it. We focused on what was missing. We agitated for things to ���go back to normal.��� As if the way things were before was how they were supposed to be!

Because of some health issues in our household, because we had the physical space, since I had some financial comfort, and because my in-person work was certainly not essential���I did not want to be responsible for getting people together and getting them sick���we continued our social distancing in a more sustainable way longer than most. I turned down work travel. I declined most social obligations. We let our employees keep working remotely.

This was one of the best decisions I ever made. I really grew as a parent���as an equal parent. I got in a lot of reading and writing and running. And as I said, I grew to really love where we live.

As Dalton writes in her book, she had the same experience.

How glad I am now that I did not leave for the city the moment it became possible. I am grateful for every additional day that I gazed out of the window. If I had gone, I would not have seen the leverets born. I would not have built the relationships I formed around the hare, with other people and with this patch of land, and felt this unexpected, uncomplicated joy, and learned not to tamp down the emotions it generates in me. I would not have looked at my life from a different perspective, and considered both what more I might be and the things I might not need. Whereas before I sought out exceptional experiences and set myself against the crowd, I take comfort in the fact that this process of self-discovery has been felt by millions before me.

Me?

I���m grateful for something like 500 consecutive bedtimes with my boys.

I���m grateful for ���the road trips we took���. I���m grateful for the projects we worked on together as a family (���designing the bookstore���, ���writing The Boy Who Would Be King��� and��� The Girl Who Would Be Free���). I���m grateful for the things it forced me to notice and work on in my marriage.

I���m grateful that it forced me to confront the reality that there are many things I don���t have to do. If you���d asked me in January 2020 if I could survive���professionally and personally���with no travel, no events, no dinners out, no get-togethers, I���d have said absolutely not. As it turned out, it was ���not only rewarding but immensely productive in every sense���. Why? Because clearly, those things I thought I had to do, I didn’t actually have to do. As it turns out, I���m better and happier when I don���t.

I���m grateful for what it taught me about human nature, about history, about adversity, about mortality, about our obligations to each other. I���m grateful that it didn���t radicalize me or turn me into an unfeeling, cruel person (what Marcus Aurelius would refer to during the Antonine Plague as the real pestilence). I���m grateful that it showed me what I needed to be most grateful for���my health, my family, the present moment. I���m grateful that it taught me how easy it can be to take so many things about our lives for granted that other people do not share and would count themselves incredibly lucky to have.

I���m grateful for what was, I think you can say, the most radical lifestyle experiment in human history. In a note to myself in the early days of the pandemic, I wrote, ���2020 is a test: will it make you a better person or a worse person?���

That was the test that I reminded myself of over and over again: will this make you a better person or a worse person?

In the process, the difficult, painful pandemic became what POW survivor, ���Admiral James Stockdale, would describe��� as a ���defining event of my life, which, in retrospect, I would not trade.���

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Published on March 26, 2025 13:59

March 13, 2025

How I’m Decluttering My Life This Spring

It doesn���t exactly keep me up at night, but like most people, I have a low-level suspicion that I���m paying for a bunch of stuff I don���t need.

At the beginning of the year, I went through all the various accounts and credit cards for my businesses, and sure enough, that���s exactly what I found.

There was an IMDb Pro account still active from a podcast producer who left three hires ago. We were paying for three cloud storage services when one would have sufficed. Somehow, we ended up with two separate enterprise Zoom accounts���and one had been upgraded to handle a large number of people on a call we were doing and was never downgraded. As I dug in, I found more redundancies, I found services that had sneakily ratcheted their fees up month after month and then just stuff I don���t think we ever signed up for in the first place.

This, of course, is a microcosm of our digital and subscription economy these days. It���s also, I think, a metaphor for life. We don���t just accumulate stuff, we accumulate drag. We accumulate drains and leeches that instead of physically taking up space, overwhelm and impede our ability to operate and think.

It turns out that the monthly cost of all these unnecessary expenses was almost enough to cover the salary of a new employee! Plus my mental bandwidth���to say nothing of the corresponding emails all these services send���was increased as well. It���s basically the same feeling I get whenever I clean out the garage or organize a doom drawer.

So that���s what I am thinking about now that spring is upon us: how I can declutter my life���physically, mentally, and emotionally���and how you can do the same.

(And by the way, I’m getting together with thousands of Stoics from around the world to do some spring cleaning as part of ���The Daily Stoic Spring Forward Challenge��� on March 20th. It���s a set of 10 daily, actionable challenges designed to help you clean up your life and spring forward without the weight of bad habits and vices. ���You can learn more and sign up here���. I hope to see you there!)

Clean up your information diet. In programming, there���s a saying: ���garbage in, garbage out.��� The question is, what are you allowing in? Many of us absorb too much garbage���whether it���s from the news we watch, the people we follow on social media, or even certain people in our lives. Spring is a great time to ask: Where do misery, negativity, dysfunction, and chaos sneak into my life? And then do something about it. Look at your ���information diet.��� When was the last time Twitter actually left you feeling informed? Reddit? Cable news in an airport? If it isn���t leaving you calmer or wiser, ���maybe it���s time to cut it off at the source���. You don���t have to be uninformed���just be intentional about what you consume and who you engage with. Personally, I prefer reading books about history and human nature (���here���s a list of timely books I put together for 2025���). They���re not all fun and sunshine���there���s plenty of darkness, too���but I learn far more from that than from endless scrolling. I���m deliberate about which chats and texts I participate in and who I spend time with. I aim to let in the opposite of garbage, because that leads to the opposite of garbage out.

Destroy a DOOM box. We all have them���those boxes, bins, or junk drawers stuffed with random odds and ends we don���t actually need. This is what���s known as a DOOM box������Didn���t Organize, Only Moved.��� In one of the few jokes Marcus tells in ���Meditations���, he writes about people who accumulate so much stuff, they don���t even have a place to shit. Seneca famously said that people aren���t just weighed down by their possessions���they are owned by them. That overstuffed box in your garage, the junk drawer spilling over, the storage closet packed with forgotten things���what are you really holding onto? If you wouldn���t go out and buy it today, why are you keeping it? Grab a bag, empty the doom box, and purge anything you don���t truly need. Whether you trash it, donate it, or sell it, clearing out physical clutter clears mental space and reduces the number of things that ���own��� you.

Quit your vices. In another sense, we can be ���owned��� by bad habits. Seneca talks about how even a powerful Roman general can be mastered by ambition. Many of us are slaves to habits or substances. There���s a story I tell in ���Discipline is Destiny��� about the physicist Richard Feynman feeling a sudden midday urge for a drink. Realizing alcohol���s hold on him, he quit cold turkey. Dwight Eisenhower, a four-pack-a-day smoker, had a heart attack and simply gave himself an order to stop. He realized he was not in command���the habit was in command. Ask yourself: What has control over me? Is it caffeine, social media, Netflix, junk food���something more serious? I once heard addiction described as losing the freedom to abstain. If you struggle to avoid something you don���t truly need���as Feynman realized���you���re dealing with a compulsion. With spring on the horizon, ask yourself what you���re hooked on. Where have you lost the freedom to say no? And how can you reclaim your power by refusing to feed that habit? For some, it���s as simple as not buying junk food. For others, it may involve support groups or a treatment program. In any case, spring is an ideal time to assess who���or what���is in command, and to reassert your autonomy. If you want a happier, more fulfilling life, decide which vices you���re no longer willing to let rule you.

Limit what has access. We are way too reachable. You have Facebook messages and text messages. People can call your phone. People can call you on WhatsApp. People can hit you up on Instagram and LinkedIn and Slack and Telegram. People can send you a package at your office and send junk mail to your house. This is insane! There should not be a DOZEN ways that people can get ahold of you. Who could possibly keep track of that? I���ve limited it to three ways people can get in touch with me: You can text, email, or call me. Email is day-to-day work stuff, texts are for friends and family, and when my phone rings, it���s usually something important from either one of those groups. I no longer feel the need to check 20 different apps and inboxes 50 times a day, because I know everything that actually matters will come in through one of those three channels.

Close the loop. I have a bunch of emails in my inbox waiting on a signature, waiting on a reply, waiting on a form or a selection. Why am I just letting them sit? It always takes less time to close these loops than I think���yet I let them sit there. I���ve found it really helpful to just dedicate, say a concentrated 15 minutes, to closing as many of them as possible. The mental relief that comes from clearing them out is always worth far more than the small effort it takes to get them done.

Delete the loop. At the same time, I have a bunch of emails that I told myself I was going to reply to but honestly, I don���t need to. Or too much time has passed for it to be worth it. So another 15 minutes where I just go through and mark these as read���or better off, delete them���is time well spent, too.

Make amends. This is actually one of the challenges in ���Spring Forward���: identify any grudges we���re holding���conflicts, disagreements, or sources of animosity in our lives. How can we clean those up or clear them out? What can we apologize for? Years ago, there was someone I got into a big fight with over one of my books. I eventually emailed them, saying, ���Hey, here���s what I���ve been carrying, and I wish I���d done it differently. I feel bad about the consequences for you. I���m sorry.��� I���d love to say we became friends afterward, but they didn���t accept my apology���instead, they hurled more anger at me. It was obvious they still carried a lot of resentment, but making amends is also a gift you give yourself. I said what I needed to say, so I���m no longer ruminating or waiting for an apology from them. I owned my role in it. I tried to be who I want to be. If they aren���t there yet, that���s okay���I did what I could. As Marcus Aurelius said, the best revenge is not being like the person who wronged you. Maybe they���ll never see your side, but at least you won���t turn into them. We can���t change the past, but we can take responsibility: acknowledge our mistakes, own the pain we caused, learn from it, practice empathy, and try to repair it. We also have to forgive those who���ve hurt us and seek forgiveness from those we���ve hurt. What we can���t do is pretend it never happened. Clearing away that emotional clutter is part of a true spring cleaning���a deep clean for your life.

Get out in nature. There���s a Japanese term I love���shinrin-yoku���which translates to ���forest bathing,��� getting outside in nature. Marcus Aurelius talked about ���washing away the dust of earthly life,��� and getting outdoors is one of the best ways to do that. Whether it���s a long walk, a bike ride, or just a quiet moment outdoors, nature has a way of clearing away a cluttered mind. I live out in rural Texas partly because I love the beauty of the natural world. Seneca called it a ���temple of all the gods.��� Yet so many people spend their lives in cubicles, offices, or cars���one sealed environment to another���missing the world���s beauty. Recently, during a trip to Utah, I went for a run, cut through a cemetery, and spotted deer running by. I returned to my hotel feeling amazing. So the question is, how are you making time for nature? You might get dusty or muddy, but you���ll come back feeling cleaner and clearer than ever.

Delegate and automate. Something I often find myself asking myself, is this something only I can do? If the answer is no���and you can afford to, delegate it. If you can���t yet afford to, automate it. Time is the most precious resource. You have to find people who are good at things and empower them to help you. You have to be strong enough to hand over the keys, to relinquish control so that you can keep the main thing the main thing and not be distracted and weighed down by the rest.

Eliminate a pointless, recurring meeting. The recurring meeting gets on our calendar for a good reason or with a clear purpose. But it doesn���t take long for it to become a ���wretched habit,��� as Musonius Rufus said. Take a look at your calendar. Ask: is this meeting still necessary? Or could the same result of a dragged-out meeting be accomplished in a couple of minutes over email? If so, time to eliminate it.

Be protective of your time. One question I regularly ask my employees���and myself���is: What���s eating your time, and is it really a good use of it? A brief ���time audit��� can be eye-opening. Think about what you spend the most time on. Maybe it started small but ballooned into an enormous time sink. Just like a nutritionist might ask, ���What are you eating?��� and have you keep a food diary, try to keep track of how you spend your day. My screen-time app, for instance, might show how much time I spend on texts, email, Instagram���then I have to ask, Is that the best use of my time? As we head into spring, it���s not just about decluttering physical items; ���it���s also about shedding ���time sucks.������ Marcus Aurelius gives us a test: Ask yourself, if I were to die soon, would I be afraid because I couldn���t keep doing this? The truth is, we often spend our time on frivolous or wasteful activities. At work, I remind my team���and myself���that if something���s taking up too much time, maybe there���s a better way. Now, before life gets busy again, is the perfect moment to identify those time drains.

Simplify your to-do list. When we were working on ������What You���re Made For������, George Raveling told me that once in a meeting at Nike, the president asked the team, ���Would we be better off doing 25 things good or 5 things great?��� George said he still applies that day-to-day. ���My day really revolves around just three or four things���I try to declutter the day and say, ���Okay, if I can get these four things done today, it will be a good day.������ As for me���every day, on a notecard, I write down 5-6 things I want to get done that day. Every day, I cross these off and tear up the card. That���s it. That���s the system.

Eliminate the inessential. We have a lot on our plates: emails to answer, calls to make, meetings, errands, groceries, kids to drop off, social media���the list goes on. Marcus Aurelius said if you want more tranquility���if you want to improve���you have to ask: Is this essential? Most of what we do or say isn���t. If we eliminate the inessential, he says, we gain the double benefit of doing the essential things better. So, to declutter your life, you have to say NO more often. Remember: No is a complete sentence. You don���t need to explain or justify it. As Seneca reminds us, many of us live in a state of ���busy idleness,��� endlessly doing things we don���t need to do. So as spring arrives (and every other season, too), keep asking yourself, Is this essential? What if you said no? How much more productive, happy, and content could you be with stronger boundaries and clearer priorities? You only have one life���stop wasting it, and stop letting people steal your time. Say no, and do less.

***

That���s some of the things I���m doing to declutter and find clarity in my life.

If you���re ready to take your own efforts to the next level, I���d love for you to join me in the ���Spring Forward Challenge��� from Daily Stoic.

It���s packed with powerful exercises rooted in the best Stoic insights and strategies, and thousands of people around the world will be participating.

Sign up at ���dailystoic.com/spring������we start on March 20th. I hope to see you there, ready to clear out the clutter and make room for what truly matters.

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Published on March 13, 2025 12:40

March 5, 2025

21 Powerful Life Lessons From My Mentor (George Raveling)

Like most people, I am a product of my mentors.

But when I talk about one of the most influential people in my life, everyone usually assumes I am referring to Robert Greene. Robert, of course, taught me so much and I continue to learn from him.

Actually���there���s someone else. Someone whose wisdom, generosity, and curiosity have shaped my life, work, and thinking more than almost anyone I���ve met. Someone who has influenced how I approach relationships, how I treat others, and how I try to give back.

That someone is George Raveling.

Who is George Raveling? I think he���s one of the most remarkable people of the 20th century. His story is extraordinary. His father died when he was young. His mother was placed in a mental institution, and he was raised by his grandmother. He went to a series of Catholic schools, thrived as a basketball player at Villanova, and after serving briefly in the Air Force, found his calling in coaching. He became the first African American basketball coach in what���s now the Pac-12 and went on to have a Hall of Fame career, leading programs at Washington State, the University of Iowa, and USC. He was instrumental in bringing Michael Jordan to Nike and has mentored some of the most influential coaches in college basketball. I���ve watched John Calipari, Shaka Smart, and Buzz Williams all call him to get his advice on something when I���ve spent time with George. In college basketball, he���s known as the Godfather.

And if that weren���t enough, George owned the original typewritten draft of the ���I Have a Dream��� speech, which Martin Luther King Jr. handed him while he was working security at the March on Washington. In an extraordinary gesture, in 2021, George donated the historic document to his alma mater, Villanova University, on the condition that they collaborate with the Smithsonian and the National Museum of African American History to loan it out, ensuring that more people can see and be inspired by it.

He���s been a mentor and friend to me, someone whose message I���ve tried to help share with the world. Most recently, I played a small role in bringing to life his memoir, ���What You���re Made For: Powerful Life Lessons from My Career in Sports���, which I pitched to my publisher. It just came out yesterday.

In this article, I wanted to share some of the many lessons I���ve learned from George over the years and in the process of working on the book with him. His wisdom and example have influenced my life in ways I never could have imagined���I hope these 21 lessons impact you as much as they have impacted me���

��� You have two choices today. George told me that when he wakes up in the morning, as he puts his feet on the floor but before he stands up, he says to himself, ���George, you���ve got two choices today. You can be happy or very happy. Which will it be?��� (Voltaire put it another way I love: The most important decision you make is to be in a good mood.)

��� Always be reading. He told me a story from when he was a kid������George,��� his grandmother asked him, ���do you know why slave owners hid their money in their books?��� ���No, Grandma, why?��� he said. ���Because they knew the slaves would never open them,��� she told him. To me, the moral of that story is not just that there is power in the written word (that���s why they made it illegal to teach slaves to read), but also that what���s inside them is very valuable. And the truth is that books still have money between the pages. My entire career has been made possible by what I read.

��� Go learn things and meet people. It���s not enough to read���you have to go down rabbit holes, look up words you don���t know, share interesting ideas with others, earmark pages, and make notes in the margins. A few years ago, George was reading a book when the word ���mastermind��� caught his eye. He���d never heard it before. As was his habit, he circled it and made a note to look it up later. That sent him down a rabbit hole���researching the concept, reading articles, and learning about an event called Mastermind Dinners. He shared what he found with a few friends, including me. As it happened, I knew the guy who ran the Mastermind Dinners and offered to connect them. ���Go for it!��� George replied. Not long after, I got a photo of him at the conference in Ojai, California. He was the oldest person there. The only one not an entrepreneur. The only one from sports. The only one retired. But by the end, he was everyone���s favorite. People told me afterward that George was the highlight of the event. He asked great questions, he listened, he shared, he made people think. He could have told himself he didn���t belong. Instead, he showed up, stepped outside his comfort zone, and kept learning���at eighty-three!

��� Keep a commonplace book. At his house, George has these big red binders filled with notes. He calls them his ���learning journals.��� They���re his version of a commonplace book���a collection of ideas, quotes, observations, and information gathered over time. The purpose is to record and organize these gems for later use in your life and work. It���s a habit he���s kept since 1972. To this day, he told me, ���I go back and just read through them. I���ll just get one of the binders and I’ll sit down at the kitchen table and start reading through it. Sometimes I come across stuff that is more applicable today than it was when I wrote it in there.���

��� Live like it���s the 4th quarter. George nearly died in a brutal car crash at 57. When he woke up in the hospital, a police officer told him, ���Coach, you don���t know how lucky you are.��� He took that to heart���treating every day after as a second chance, an opportunity to do more, learn more, and give more. He went on to have a whole second act, joining Nike, shaping the future of basketball, and achieving things he never imagined. We shouldn���t need a near-death experience to wake us up to what we have. Seneca put it well: Go to bed each night saying, I have lived. If you wake up, treat it as a gift.

��� Learn from everyone. George once said in an interview that I was his mentor, which, of course, is preposterous. But I���ll take the point: you can learn from anyone. It doesn���t matter if they���re younger than you, if they live a completely different life, or even if you disagree with them on 99% of things. Everyone can teach you something. Anyone can be your mentor.

��� Do the most important thing. When George became Nike���s Director of International Basketball at 63, he had no prior corporate experience and was overwhelmed by self-doubt. Until a mentor gave him a simple system: ���When you leave the office every day, leave a yellow pad in the middle of the desk, and when you come in the morning, write down the three most important things you gotta get done that day in that order. That day, do not do anything else but the first thing on the pad. And if you get the first one, then you go to the second one.��� That structure put order to his day and gave him a sense of purpose. Instead of spinning his wheels or getting lost in distractions, he focused on what mattered most. One thing at a time.

��� Choose opportunity over money. George once told me, ���Never take a job for money. Always take a job for opportunity.��� That���s how he���s lived his life, and that���s why he���s had such an incredible life. It���s why he took the job at Nike, not despite the fact that he had no experience as a global corporate executive���but precisely because he had no experience as a global corporate executive. It was a chance to step into something completely new, to learn, to grow, to challenge himself. He didn���t take the job because it was safe. He took it because it was filled with opportunities���to meet fascinating people, travel the world, immerse himself in different cultures, and bring the game he loves to new places and new people. Most people would have stuck to what was comfortable and familiar, but George went where the opportunity was.

��� Always be prepared. When we were working on ���What You���re Made For���, George and I had weekly calls that ran for one to two hours. It was my job to pull stories and lessons out of him. George is obviously the boss and the questions were largely about his life, so it could have been pretty relaxed, but that���s not his style. He clearly spent hours preparing for each hour we were on the phone, always coming intensely prepared with notes, questions, and ideas ready to go. He treated every call the way I imagine he prepared for a big game back in his coaching days or a high-stakes meeting at Nike. In one of our calls, he told me, ���Right to this day, I think it���s disrespectful to go into a meeting and not be prepared.���

��� Trust is earned. George and Michael Jordan have known each other for decades. Their relationship is built on trust���so much so that George told me, ���Other than my mom and my grandma, never in my life have I had anybody who trusts me as much as Michael Jordan.��� And he���s never done anything to jeopardize it. In all their years of friendship, even when he ran Michael���s basketball camps for 22 years George said, ���I���ve never asked Michael for anything in my life���no money, no tickets to games, nothing.���It shouldn���t be a surprise, then, that when George told Jordan he should seriously consider signing with Nike, Jordan listened. That billion-dollar decision was the result of the trust Coach built when he coached Jordan on the ���84 Olympic Team. As Jordan writes in the foreword (not something he does often!) to What You���re Made For, ���There are all kinds of stories out there, but George is truly the reason I signed with Nike. As I���ve said before, I was all in for Adidas. George preached for Nike, and I listened.���

��� Practice the art of self-leadership. George once told me, ���One of the most underrated aspects of leadership is our ability to lead ourselves.��� Before you can lead a team, a company, or a family, you have to be able to lead yourself. And isn���t that what the Stoics say? That no one is fit to rule who is not first ruler of themselves?

��� Be a positive difference maker. George has a powerful question he often asks: ���Are you going to be a positive Difference Maker today?��� It���s a question that challenges you to think about the impact you want to have each day. I think about it all the time.

��� Find the good in everything. George once texted me out of the blue, ���I am absolutely unequivocally the luckiest human being on planet Earth.��� He sees everything that’s happened to him, even the terrible things, even the adversity, even the unfair things. He sees them as all leading up to who he is now. He walks through the world with a sense of gratitude and appreciation and a belief in his ability to turn everything into something positive.

��� Tell them what they mean to you. When we would do our calls for the book, it caught me off guard at first. George, before hanging up, would say, ���I love you.��� I���m not used to that���at least not from people outside my family. But George never hesitated. ���I���ve learned that it���s hard for people, especially men, to say ���I love you,������ he told me. Even with his own son, he noticed that for years it felt uncomfortable for him to say it back. ���It���s strange,��� George said, ���because every one of us has a thirst to be loved, appreciated, acknowledged, respected. And yet, for some reason, we struggle to express it.��� So George has made a habit of saying things like, ���I appreciate you.��� ���I respect you.��� ���I���m glad you���re my friend.��� ���I���m here for you.��� Simple words that so many people rarely hear. George didn���t assume people knew how he felt���he told them.

��� It���s up to you. George used to give a talk at basketball camps titled, ���If it���s to be, it���s up to me.��� He said, ���At the end of the day, either our hands are gonna be on the steering wheel of our lives or someone else���s hands are gonna be on the steering wheel of our lives.���

��� Do less, better. Once in a meeting at Nike, the president asked the team, ���Would we be better off doing 25 things good or 5 things great?��� George said he still applies that day-to-day. ���My day really revolves around just three or four things���I try to declutter the day and say, ���Okay, if I can get these four things done today, it will be a good day.��� Every day, on a notecard, I write down 5-6 things I want to get done that day. Every day, I cross these off and tear up the card. That���s it. That���s the system.���

��� Cultivate relationships. While we were working on the book, George told me, ���Often people say, how do you account for what���s happened to you in your life? And the one word I use to capture it all is: relationships. My whole life has been built on relationships. People seeing something in me that I didn’t see in myself.��� When I look at my own life, the most pivotal moments, the biggest opportunities���they all came from relationships. From people who believed in me when I didn���t believe in myself. Relationships aren���t just about networking; they���re about surrounding yourself with people who see your potential, sometimes before you do.

��� Build your team. George sometimes refers to his family as Team Raveling, and his wife, Delores, as the CEO of their family. He talks about how too many people put more thought, effort, and strategy into their careers than they do into their families. They chase professional success with careful planning, clear goals, and relentless discipline���but expect their relationships to work out on their own. You wouldn���t expect a company to succeed by just winging it. A family is no different���it can���t thrive without leadership, communication, clearly defined roles, and a shared vision. Whether it���s your spouse, close friends, or a chosen family, you have to build your team with the same intention and commitment you bring to your work.

��� Listen. George is one of the best listeners I���ve ever met. He says, ���The quality of your conversations is greatly dependent on the quality of your listening.��� I used to think I was a good listener, but watching George taught me how much better I could be. He doesn���t just wait for his turn to talk���he listens to understand.

��� Become the go-to. When George was a player at Villanova, initially, he wasn���t getting much playing time. So he looked around and noticed something: no one on the team was a great rebounder. And he figured if he became the best rebounder on the team, his coaches would have no choice but to play him. So he made it his role. He invented his own rebounding drills and practiced them every day. By the time he graduated, he had set multiple rebounding records and was one of the best rebounders in the game. I love the idea of inventing a role for yourself���finding something that���s being overlooked or not addressed and deciding to become the go-to person for it. It���s not just a good strategy for athletes���it���s a way to make yourself indispensable in any field.

��� Know your boundaries���and enforce them. I once connected George with someone interested in working on a project with him. Everything was going well���until they sent over the proposed terms. George didn���t argue or negotiate. He sent back a clear, firm email terminating the discussion. The other party was surprised and followed up to ask why. ���The offer was insulting and ridiculous,��� George explained. He didn���t waste time debating or trying to make it work. He knew his worth, and he wasn���t going to entertain anything less. Too many people accept bad deals out of fear or politeness, but George believed in setting clear boundaries���and enforcing them.

I will leave you with this…

Although he���s famous for being a coach, that���s not what it said on the door of his office. Instead, it said,

George Raveling

Educator

He, to this day, sees himself as a teacher. And he teaches by example, by how he lives his life. That���s why, even though I never played for George Raveling, I���ve learned so much from him. By watching how he carries himself, how he lives, and how he treats others, I���ve learned more than I ever could have from words alone.

���And you can, too���.

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Published on March 05, 2025 14:27