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RyanHoliday.net - Meditations on strategy and life
Blog

39 (Or So) Lessons On The Way To 39

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Well, I’m now almost 40. Like officially almost 40. I woke up yesterday in Cle Elum, Washington, ran 20 miles and then turned 39. I did a little talk for Amazon and then flew home, getting in very late and very tired. 

I have been doing some version of this post for basically twenty years. 

(You can see my birthday posts for ​26​, ​27​, ​28​, ​29​, ​30​, ​31​, ​32, ​​33​, ​34​, ​35​, ​36​, 37, and 38​). 

How much have I learned and changed? Quite a bit, I’m proud to say. Not enough, I’d have to add much more honestly. I still fall prey to the same patterns. I am still doing too many of the same things. And worse, I’m still too often not aware of it until it’s painfully obvious much later. Which brings me to my first lesson for this year’s list. 

– At my talk in Seattle last week (I’m on tour this summer and fall if you want to come see me in the US and Australia), someone asked how I would describe myself in one word. I thought about it and I just said: “Trying.” I’m trying. Could I try a little harder? Would I like to make a little more progress? Yes. But I am trying. 

– I’ve given hundreds of talks now, and I could give the same one every night, the same way, until I had it down cold. Instead, I try to change it each time—I add things, I cut things, I work out new material right there on stage. If I have the opportunity, because of the audience or whatever, to give a totally new one that I haven’t done before, I see that as a gift not an obligation. Because harder is what makes me better. It also keeps life interesting. 

– One of the things that sneaks up on you as you get older are the blocks of time you can start measuring things in. For a while, four years—the length of high school or college—is a measuring stick of something that takes a while. Then you get comfortable with things being a decade long—“We’ve been friends of a decade” and “That was like ten years ago?”—and then suddenly, it’s twenty years, like I did in the intro above. I had my twenty year high school reunion last year. This gives you perspective. You start to get a sense of how long things take and how much capacity you have to endure or live through.

– And yet even so, the passage of time can sneak up on you. I was looking at a baseball picture of my son the other day. It was him holding a bat, looking basically like the kid he is now, except it says 2025. How could he be old enough to at one point have been five years younger? I was trying to express to him how unbelievable that is to me. But it’s true. Tempus fugit the ancients said. Time flies. Be present. Be ready. 

– I don’t believe in time travel…but I do believe the work—learning, research, exercise, etc—is a gift we give our future selves. Basically, you can’t make withdrawals from accounts you haven’t made deposits in.  

– The purpose of any piece of writing at all is not the end product on the page. It’s the person YOU are on the other side of having done it. It’s the thinking long and hard about something. It’s the slow, tedious, difficult work of figuring out what you actually work. And the equally hard work of finding the words for what you think. AI can give you an essay, an article, a book, or a briefing. What it can’t give you is the person you can only become by doing the writing yourself.

– “It is surprising,” Roosevelt said, “how much reading a man can do in time usually wasted.” That’s exactly right. Bring a book with you everywhere. 

– I don’t think I have ever taken a walk without thinking, after, “I am so glad I did that.” We rescued a dog last year and that’s been the best part. It’s “forced” me to do something I love to do. 

– For fifteen years (again those chunks of time!) I’d had this idea sitting in the back of my head, and last July I finally did it: I ran the 26 miles from Marathon to Athens. On the Daily Stoic podcast, Jesse Itzler told me about this concept of the Misogi. Borrowed from an ancient Japanese purification ritual, the modern Misogi is about committing to one epic, year-defining challenge—something so significant, so hard, so memorable, that decades later, when you think back, you’ll instantly remember: that was the year I ___________________. When I look back on 2025, I’m going to think, that was the year I ran the original marathon in Greece. In a couple weeks, I’m going to try to do my Misogi in Rome. I’ll let you know how it goes. 

– We are flooded with more information than entire civilizations could have produced, let alone imagined. And yet, how much of this matters? Or even holds up? When I was talking at Amazon, I brought up one of their company values which is “focus on the things that don’t change.” But how much of our information diet adheres to that? How much of what we give our attention to day to day, supports us in our goal to be long term thinkers? 

– Obviously I am biased as an author but I think most people should consume less news and read more books. Less news, more books. More history. More poetry. More literature. More philosophy. More myths. Because you know what those stories are about? They’re about what’s happening now!

– Almost every lesson you need to learn to deal with what’s happening in the world, almost every skill you need to develop to succeed in modern times is the topic of old art. I was bowled over last summer when I read Euripides’ The Children of Hercules. It’s a play from 430BC and I’d never even heard of it. In it, the young children of Hercules are driven to the Temple of Apollo in Marathon by a bounty hunter from an angry king, who demands they be handed over to be punished. “They are suppliants and strangers,” the Athenians reply, “Who look to our city for help. / To reject them is to defy the gods.” The people of Marathon have to decide. In theory they care about the plight of the refugee, they know what their values say to do. But how much are they willing to risk for strangers? Is their compassion a match for the animus and anger of the fearful and the angry? Anyway, as Truman famously said, “the only thing new in the world is the history you don’t know.”

– Again, supreme irony: AI, this cutting-edge technology, actually makes the oldest skills more valuable than ever. Reading. Thinking. Knowing things. Empathy. Having taste. Understanding context. Detecting lies or nonsense.

– That last one is really important. The essential skill of our time is having a good bullshit detector. Can you spot an obvious agenda? Can you recognize legit craziness? Can steer clear of bad actors and grifters? I have been amazed at how bad people seem to be at this, especially people who host podcasts. C’mon guys. Do better. 

– One of my favorite things to do each day is sit down and write the ​Daily Dad email​. It’s one piece of wisdom—drawn from history, science, literature, and other ordinary parents—that goes out to about 100,000 parents around the world (sign up here). But really, I’m writing it for myself. Again, the purpose of any piece of writing is the person you are on the other side of having done it. We write to figure out what we think and believe. Which is something you can’t have someone else do for you. The point is to do it.. 

– You’re going to look back on this period and wish you did more. I don’t mean work. I mean you’re going to wish you were more active and outspoken. That you went against the political current, that you lent a hand, that you participated. This fever will break (or rather, it will be broken) and we will all be judged. We will judge ourselves. 

– Related: I want to quote again some advice I got last year when I was weighing whether to say something I knew might cause me some problems. It came from a four star admiral: “I think you should just speak directly about what you truly believe. That is always a path.”

– And related even more: When you do this, you are doing the world a service. Courage is a team sport. Justice is a team sport. People are far more likely to stand up, to say “this is wrong,” when they’ve seen someone else do it first. So when you speak up, you’re not just taking a stand. When you are unapologetically yourself, you’re not just being yourself. You’re making it easier for the next person to. 

– Everyone could use a support group. A circle of people who’ve been there, who give you advice, who relate to what you’re going through. When my first son was born, I wanted that and couldn’t find it for dads, so I built one, Daily Dad Society. A little over a year in, the conversations in our monthly live calls have changed how I parent. (Dads, join us!)

– You might think you’re zooming out to see the big picture, but almost certainly you can open the aperture even more. I was talking to Senator and retired astronaut Mark Kelly on the Daily Stoic podcast about a line in Meditations where Marcus Aurelius is talking about looking at the city from above, trying to imagine what Earth looked like from the stars as a way to “wash off the mud of life below.” He responded by saying, “Now imagine if Marcus knew that we were one galaxy in a universe of two trillion galaxies.” So good. 

– When we moved out to rural Texas in 2015, there was basically no cell phone service at our house or on our dirt road. We tried to fix it—I even put a booster on the roof—but it didn’t work. We could have switched providers, but that seemed like a pain. So we got used to it. For over ten years, when we were out and about at home, our phones couldn’t make calls or send texts. It was almost predictable: I’d be back somewhere on my property and some incredibly important call would come through with just enough service for me to answer and not be able to talk. That’s why it snuck up on me the last couple months that my phone had full reception when I was out checking on the cows. Or walking the dog. Or even out in the garage. An inconvenience that had been part of our lives for so long just suddenly went away. And it took me some time to notice it. I guess that’s my point: Life doesn’t always get worse. It often gets better…and we don’t even notice. 

– A lot of people read, not enough people re-read. Don’t just read books, re-read books. There’s a great line the Stoics loved—that we never step in the same river twice. The books don’t change, but you do. I re-read The Road and The Great Gatsby (there’s an incredible new annotated 100th-anniversary edition that came out last year with tons of fascinating asides that provide a ton of new context) this year. Both hit me very hard, which of course, is what the best literature does. 

– How well do those first two sentences in Gatsby hold up by the way?

In my younger and more vulnerable years my father gave me some advice that I’ve been turning over in my mind ever since. “Whenever you feel like criticizing any one,” he told me, “just remember that all the people in this world haven’t had the advantages that you’ve had.”

– And for The Road (which I did a long interview for The New York Times about)? The idea of ‘carrying the fire’ / being ‘one of the good guys’—that’s what life, what parenting, what making it through this crazy period of history is all about. As I quoted Stefan Zweig in last year’s birthday post: we must “remain human in an inhuman time.”

– The novelist Philipp Meyer (whose book ​​The Son​​ is an incredible read) told me on the podcast, “You have to be very careful about what—and to whom—you’re giving the best part of your day.” Wake up, scroll, check email, meetings, busy work, whatever—why do we hand the best part of our day to other people’s emergencies and agendas? I fiercely protect my mornings—family, exercise then writing. I want to give my best self to my most important things.

– Where do your own emotional patterns get in the way of clear thinking? When you’re hurt or betrayed or unexpectedly challenged, pay attention to how you react. Notice the “age” of that reaction. Is it mature, measured, proportional? Or does it feel more like a wounded eight-year-old lashing out? That’s your inner child—the pain you still carry from early experiences, hijacking your adult mind.

– To go to Euripides’ point about the refugees and the weak: There is no such thing as an issue that doesn’t affect you. People thought the crack epidemic was an urban issue…if they’d responded with more kindness and support (and solutions instead of punishment and fear), perhaps the country would have been better equipped to deal with the opioid epidemic. We will come to think the same about many other things in the future…

– 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? What can only we write? What can only we create? Don’t be like everyone else. Be yourself! That’s where you have a monopoly. That’s something Iron Maiden’s manager once said—that he wasn’t in the “music business” as some people thought, he was in the “Iron fucking Maiden business.” 

– The reward for success should not be that you don’t get to practice your craft anymore. If power gives you less power over your schedule and your day, is it actually power?

– When we were working on ​​​What You’re Made For​​​, the late George Raveling—who I think is one of the most remarkable people of the second half of the 20th century—told me that when he became Nike’s Director of International Basketball at 63, having no prior corporate experience, he 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.” If you just did that, how much better would you be? How much better would the world be if people could consistently do just that? 

– I’ve been keeping a One Line a Day journal for nine years now (you should keep one, they’re amazing). It’s weird how much you don’t remember, even of your own life. But my favorite part of the journal is when things line up. This day last year, I was working on my next book which starts in media res. Today, I sat down to work on the book and I have almost come back to the starting point. I love that. Half way left! 

– As I’ve made some money over the years, I’ve tried some expensive things. I’ve done the things that people use their money to do—whether it’s upgrading travel or living conditions or hiring help. Most of the time, it’s honestly not worth the money. Or it’s not as great as you think it’s going to be. 

– The one exception—in the last two years, my kids ended up at a very expensive school that’s specialized for their needs. I will say, that’s maybe the one thing where I really felt like I was getting what I paid for. Would I love it if their local public schools could do that (since via my taxes I am also paying for that)? Yes, of course. And maybe, hopefully that will change in the future. But right now it reminds me of the Marcus Aurelius quote about what he learned from his great-grandfather, “to hire good private teachers, and to accept the resulting costs as money well-spent.”

– The antidote to shame/guilt, I was told, is total accountability. 

– You think the rich and powerful have it all. But they’re some of the most jealous people alive—not just of each other, but of ordinary people with freedom, with time, with happiness. And you can have those things easily. In fact, you may well have them right now. You do not need to strike it rich…you were born rich. You do not need to climb to the top…you can simply step off the treadmill. Or at least some of them.  

– I said ‘No’ to a pretty big opportunity over the summer. There were a bunch of reasons I passed but the one I kept thinking of was “Was this exciting but ultimately selfish choice the thing that blew up my family?” I would like to stay married. I like to be able to pick my kids up from school—not be away from home many nights in a row. So in the end, the choice was clear. The point is: You have to know what you like about your life to be able to evaluate the opportunities that arise. 

– There’s a scene in Mad Men where a young copywriter who’s grown to hate Don Draper corners him in the elevator: “I feel bad for you.” Draper just looks at him and says, “I don’t think about you at all.” It’s a great line especially because Don Draper was horrible and did horrible things to people! The people who take up the most space in our heads usually aren’t thinking about us. They aren’t being awful to torture us. There’s nothing personal in it. And we are adding insult to injury when we let them consume our sanity and happiness. 

– How many times have I heard The Smashing Pumpkins’ Tonight Tonight? Hundreds easily. I don’t know why it wasn’t until a couple weeks ago, when it came on randomly in a playlist, that that lyric hit me. 

Time is never time at all 

You can never ever leave 

Without leaving a piece of youth

– Not just our youth, but our middle age and our golden years. Our children’s youth, the best years of a marriage, of a career, of anything. There is a cost to everything we do, everything we agree to, every commitment we make. We have to spend our time wisely because we are paying for it with our lives. 

That’s the message I always give a little extra consideration on my birthdays, but it’s a thought that shouldn’t ever be far from our minds. 

Memento Mori.

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June 17, 2026by Ryan Holiday
Blog

This Is Something You Have To Get Good At

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I’ll tell you, very few people become writers because they want to stand up in front of a room full of strangers and talk.

Often, in fact, it’s the opposite. What draws most people to writing in the first place is that they’re introverts. At least, that’s what drew me! We like to sit quietly, alone in a room, working through our thoughts on the page. That’s the whole appeal.

So one of the strange ironies of having any success as a writer is that you are then invited to do the opposite of that. To leave your quiet room. To get up on a stage. To talk in front of people. 

It was actually before my first book even came out that I got my first invitation to talk at an international marketing conference. And I remember thinking: this is precisely the thing I became a writer to avoid.

But over time, I started to feel differently about it. Partly because they weren’t just inviting but offering to pay, but also because I could see that it was a way of reaching people that really matters. People don’t just want to read the things you’ve written and shaped on the page. They want to hear you talk about them. They want it straight from the horse’s mouth. Think about the State of the Union Address. For over a century, the president didn’t deliver it as a speech—it was just a written report sent over to Congress, the “President’s Annual Message.” But eventually, people realized there are things you just can’t get from a letter. They wanted to hear the president say it. To watch him explain it. To hear which words he stressed and which he didn’t.

And then there’s the fact that public speaking is just part of life. There is no line of work where this is actually avoidable. An entrepreneur has to get up and pitch investors. A coach has to get up and address the team. A professor has to deliver lectures. A salesperson stands before a skeptical group of buyers. A freelancer has to sell themselves to a potential client. An athlete has to talk to the press. A friend has to get up and give a wedding toast. My nine year old and six year old just had their school’s annual showcase.

We will all have to leave our comfort zone from time to time. Yet many of us would almost rather die than do this. The comedian Jerry Seinfeld once noted that people rank public speaking as worse than the fear of death, which means, quite insanely, that at a funeral the average person would rather be in the casket than delivering the eulogy.

In Courage Is Calling, I tell the story of Crassus. In ancient Rome, there was perhaps no better orator than Crassus, famed for his brilliant speeches and prosecutions of the corrupt and the evil. At least that’s how he appeared to his audiences. You would not have known, as he later admitted, that at the outset of every speech he would “feel a tremor through my whole thoughts, as it were, and limbs.” Even as a master, he still experienced doubt—still felt waves of overwhelming anxiety and fear crash over him before he went onstage.

At the beginning of his career, it was even worse. He recounts his eternal debt and gratitude to a judge who, at one of Crassus’s first public appearances, could tell how “absolutely disheartened and incapacitated with fear” the boy was, and adjourned the hearing until a later date. We can imagine those merciful words from the judge, sparing Crassus as he no doubt prayed he would be spared, as we have prayed a thousand times, second only to his hope that he might be struck down and killed rather than have to go on.

Yet we would not be talking about Crassus had he not cultivated the ability to push through that fear. There are unfortunately no tricks to cultivating this ability. You can’t read your way to it. You can’t think your way to it. You just gotta do it. You make the pitch. You get up on the stage. You deliver the pre-game speech. You give the toast. And then you do it again and again. 

That’s what I was telling my sons and one of their nervous classmates. I get stage fright too. It is scary to get up there. But it gets less scary the more you do it. Confidence is built by competence, there’s no way around it. 

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Come see me take the stage to talk Stoicism on the Daily Stoic Live tour—grab tickets here!

There’s another irony in all this. The philosophy I’ve spent my life writing about isn’t really a written philosophy at all. Because so much of Stoicism comes down to us in books, it’s easy to think of the Stoics as writers.

Isn’t that how we got Meditations? Or Seneca’s Letters?

Yes. But that’s not how we got the philosophy itself.

Stoicism began on a porch in Athens—the Stoa Poikile, the “Painted Porch”—where Zeno would talk and trade ideas with whoever happened to be around. The playwright David Mamet had a good way of putting it: what he loves about the Stoics is that they were just “porch guys.” Regular people, hanging out, talking about how to become the best version of themselves.

Cato, the man widely admired as the greatest Stoic of them all—there isn’t even a secondhand record of his words. We know that he liked to do his philosophizing on foot. Plutarch tells us he would take meandering walks through Rome, talking with whoever he met “on his rounds.” And for all his austere habits, his other practice was hosting philosophical dinners, where he talked about ideas long into the night.

Epictetus never wrote anything down. His Discourses comes from a student, who tells us that “whatever I used to hear him say I wrote down, word for word, as best I could, as a record for later use of his thought and frank expression.” That’s how Epictetus taught—in person, going back and forth in real time.

So for most of its history, Stoicism was a spoken, conversational philosophy. It’s meant to be heard, meant to be talked about, meant for that back and forth. And this is a long, unbroken tradition that goes back thousands of years, one that continues to this day.

I’m thinking about all this because I happen to be right in the middle of it. As I write this, I’m preparing for the Daily Stoic Live tour. I’m going to be spending a good chunk of the rest of the year making the rounds, talking Stoicism all over the world: Portland (on Monday!), San Francisco (on June 11th), Chicago, Boston, and a bunch of other U.S. cities, before heading all the way to Australia and New Zealand in October. Night after night of overriding that introverted part of me that would rather just stay home and write.

Over the years, though, this is something I’ve really tried to get good at. I’ve done it hundreds of times now. In big venues and small venues. To American audiences and international audiences. With slides and without slides. With technology and with no technology. Long talks and short talks. 

And I’ve come to see it as a meaningful and exciting way to share these ideas with people, but also as this high-wire act that forces me to get better. That’s why I don’t make it easy on myself. I could give the same talk every night, the same way, until I had it down cold. Instead, I’m changing it each time. I add things. I cut things. I try one delivery one night and a different one the next. I prepare some stuff I know works, and some new stuff to work out right there on stage.

Because that makes it harder. And harder is what makes me better.

So now…I’ve got to get back to preparing to talk to rooms full of strangers. Hope to see you there!

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June 4, 2026by Ryan Holiday
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My Office Explained in 13 Objects

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When I first moved in, six years ago.

If you walk into the locker room or practice facility for a professional sports team or elite college program, one of the things that strikes you is what they put up on the wall. 

The walls are tattooed with precepts. Every hallway and doorway is decorated with motivational quotes. There are statues of former players and coaches, the legends who set the standard. There are framed photographs of the greatest moments in the team’s history.

Why do they do this?

Because reminders are powerful. They make you better. They give you something to hold up and try to live up to each day. They turn the habits, standards, or values you’re trying to hold yourself to into something more than an idea, and that helps—a lot.

I do something similar in my office. It’s filled with little knicknacks and pictures. Reminders and totems. Things I’ve collected over the years that mean something to me. Objects that represent who I’m trying to be, what I’m trying to do, how I want to work and live.

Here are 13 of them—and what they’re there to remind me of.

1. A “No” Sign

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A few years ago, Dr. Jonathan Fader, a sports psychologist who spent nearly a decade with the New York Mets, gave me this picture of Oliver Sacks in his office. Behind Sacks, who is speaking on the phone, is a large sign that just says, “NO!” I have it hanging between two pictures of my kids—a reminder that when I say no, I am saying YES to them. 

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I have that photo hanging on the wall in my office, just a few feet from a couple of Truman memos. One, from 1969, politely explains his long-standing policy not to answer questions from every random person who contacts him—he was eighty-five, still working, sensing his time was limited. The other is a brief reply telling someone that their question would be answered in detail in his next book. But the one I like the most has Truman’s handwriting on it. Shortly after he became president, Truman was invited to the fifth annual Roosevelt Day in Chicago. His secretary wrote an inner-office memo to ask if they should start saying no to these sorts of requests with all the demands he had on his schedule. “The proper answer underlined, HST”, he wrote back.

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I once heard someone say that early in our careers, we say yes to everything so that one day we can afford to say no. As I’ve been lucky enough to succeed as a writer, I’ve watched my inbound requests skyrocket. It is literally impossible to even read, let alone reply, to everyone and everything.

Life is about tradeoffs. It demands that we be a little selfish. It requires that we tune out and tune in. Otherwise we can’t do what we do.

The photos and letters are my constant reminders that everything I say yes to is taking me away from my family who I’ve already promised most of my time to. And from my writing, which is not only the thing that is most meaningful to me and how I make my actual living, but it’s how I can help the most people. So if I say yes to one random person, I’m saying no to a lot more people by taking that time and energy away from my writing.

2. Books. Books. Books.

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This isn’t one object. It’s hundreds of them. Thousands, actually. I have books lining the walls, stacked on the floor, piled on my desk, crammed into every available surface.

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It’s been said that a house without books is not a home. Cicero famously said that all that was needed for a happy life was a library and a garden. Aristotle filled his house with so many books that Plato nicknamed it “the house of the reader.”

I don’t know if my office qualifies as a proper library, but it’s close. And there’s a reason for that. I want to be surrounded by the best thinking of the last few thousand years. I want history’s greatest minds within arm’s reach. I want to be able to look up from my desk and see the spines of books that have shaped how I think, how I write, how I live.

In Wisdom Takes Work, I talk about how books allow us to talk to the dead. A shelf full of books allows us to create a room full of mentors, waiting patiently to be consulted.

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They don’t demand anything. They just sit there, ready, until you need them. That’s the kind of company I want to keep.

3. My “Why”

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This notecard is tapped to the wall next to my desk

I’ve been very lucky. I did not think when I started writing The Obstacle is the Way more than ten years ago that it would sell nearly as well as it did or that I would have anything close to the success—or platform—that I’ve somehow found myself with. I loved the ideas in Stoicism and was just trying to talk to people about them. I have no formal training or expertise, so I had no idea that I would somehow be identified with them, or seen as a representative of them. 

What this means to me then, as I look at the fact that the books have sold millions of copies and accumulated millions of followers, is that I have a certain responsibility and obligation. I did not invent this philosophy. It is not mine. So yes, writing books is a business. My bookstore, The Painted Porch, is a business. Daily Stoic is a business. But I always try to ask myself not if I am making good business decisions, but am I being a good steward of Stoicism, of the philosophy that’s given so much to me? Am I being honest and ethical and fair and reasonable and moderate?

That question guides everything we do. How we spend our time and money. The content we make. The decision to stop spending money on advertising. The causes we support. The injustices we speak out about. Not all of these decisions are good for business. Some are not popular. Some make people mad. Some have probably cost us business. 

But the filter isn’t if I am making good business decisions. It’s if I am being a good steward of Stoicism, of the philosophy that’s given so much to me. Am I being honest and ethical and fair and reasonable and moderate? Am I using the success that this philosophy has brought me to introduce more people to the philosophy? That’s my goal.

4. A Grammy?

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Years ago, I was an associate producer on a jazz album that won a Grammy in 2017. I got to walk the red carpet and go onstage and accept it. It was pretty surreal. Afterwards, they gave us a paper certificate instead of actual trophies for everyone involved. So I had this one made with a special inscription on it: 

When you die, this will go in the trash alongside all your other “accomplishments”

It’s a reminder that awards, bestseller lists, medals, championship rings—none of it really matters. They’re just pieces of metal, bits of glass, plaques on a wall. Stuff that will end up in an estate sale or a box in an attic or a landfill.

In the end, what matters is who you were as a person. Did you do your best while you were in the game? Did you leave anything on the table creatively? Did you phone it in or did you give it everything you had?

That’s what matters. Everything else is garbage.

5. Joan Didion’s Chair

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Speaking of estate sales…

After Joan Didion died, her estate auctioned off some of her belongings, and I bought her writing chair.

Last year, I was sitting in it, working on a chapter in Wisdom Takes Work about the importance of keeping a commonplace book. I pulled out my notecards and found an old, worn card referencing something Didion had written about notebooks in her book Slouching Towards Bethlehem. I walked over to the shelf, pulled it down, and there it was—a beautiful essay called “On Keeping a Notebook,” written in 1966.

I got goosebumps. Not just because it was exactly what I needed, but because I was sitting, at that very moment, in her chair. How did I know, nine years ago when I first read that book, when I took the time to jot that little reference on a notecard, that it would be of use to future-me?

“Why did I write it down?” Didion asks in that essay. “In order to remember, of course, but exactly what was it I wanted to remember?”

Anyways, Didion was, like me, from Sacramento. And when I see her chair, I think about where I’m from and where it’s possible to go. I think about how I’m not alone in this work. How I’m part of a long tradition of writers and thinkers and note-takers stretching back centuries. How the craft has been handed down, and it’s my job to honor it.

6. Notecards and Notecards and Notecards

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And speaking of the importance of keeping a commonplace book…

I think everyone should have a commonplace book, or, to use a more modern term, a second brain—a collection of ideas, quotes, observations, and information gathered over time. (Here’s a video on my commonplace book method).

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Two thousand years ago, Pliny the elder said, “Never read without taking extracts.” Seneca put it another way: “We should hunt out the helpful pieces of teaching and the spirited and noble-minded sayings which are capable of immediate practical application—not far far-fetched or archaic expressions or extravagant metaphors and figures of speech—and learn them so well that words become works.”

That’s why I keep blank notecards everywhere. I’m constantly capturing quotes, stories, ideas, observations—anything that strikes me. 

Whether we’re beginning some creative work or we’re trying to solve some complex problem, we should never be starting from zero. Invariably, at some point in our lives, we have seen or read or heard something that would be of use in this situation. But will we remember it? Will we have access to it?

It happens to me all the time. I’m working on something, stuck, not sure where to go next—and I reach into a box and pull out a notecard I wrote five or ten years ago, and it’s exactly what I needed. And every time this happens, I’m grateful I took the few seconds to write the thing down.

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7. The Four Virtues 

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I mentioned earlier that sports facilities are filled with reminders—signs and symbols placed in spots where players can’t miss them. Above the tunnel. Outside the weight room. On the way to the field.

On the wall coming down the stairs from my office, I had the Four Virtues logo painted on the wall. Every time I leave to go down into to the bookstore or out into the world, I pass it.

Courage. Temperance. Justice. Wisdom.

The “touchstones of goodness,” Marcus Aurelius called them. They’re known as the cardinal virtues—not because they come down from church authorities, C. S. Lewis pointed out, but because the word comes from the Latin cardo, meaning hinge. They’re pivotal. The stuff that the door to the good life hangs on.

There’s a reason the four points on a compass are called the cardinal directions. North, south, east, west—these four virtues are a kind of compass (there’s a reason that the four points on a compass are called the “cardinal directions”). 

They guide me. They show me where I am and where I’m trying to go.

8. First Draft Print

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The famous Hemingway line on writing helps me through every book.

I’m in the middle of my next book right now, for instance. It’s natural to instinctively compare it to the ones that have been published. But that’s not a helpful comparison, and it’s not a fair comparison. Precisely zero of those other books were immediately accepted by my publisher. Every one of them went through countless drafts to get to where they needed to be.

So I can only compare this book I’m in the middle of against the middle of my other books—not what I eventually published. It’s helpful to have the constant reminder: every book—not just mine—looks and feels clumsy and awkward and imperfect at this point.

Precisely zero of my sixteen books were immediately accepted by my publisher—and they were right to kick them back at me. In being forced to go back to the manuscript, I got the books to where they needed to be.

9. A Very Special Pinecone

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When I was reading John Vaillant’s book Fire Weather (he also wrote The Tiger), I learned about this conifer tree I’d never heard of before. 

It’s like any other pine tree: it drops its pinecone and the pinecone is what generates the next generation of trees. Except this species is different. The cone is sealed shut with resin, locking the seeds inside. It only opens up—only looks like the one I’m holding in the picture above—if it’s exposed to temperatures that the climate does not naturally reach. It’s only a forest fire, which seems destructive and merciless and awful, that can unlock this tree’s ability to spawn and grow. 

I have a few of these pinecones sitting on my desk. To me, they’re an illustration of the idea that the obstacle is the way. Unless we are exposed to difficulty and stress and adversity and situations that we did not want, we can’t fully become what we’re capable of becoming. We can’t fully unlock our potential.

10. Me, But Younger

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On the back cover of Anthony Hopkins’ memoir (which, to my disbelief, I was mentioned in), there’s a photograph of him at three or four years old, on a beach with his father. Looking back at that photo eighty years later, Hopkins said, “I look now at my life, and I think, ‘We did ok, kid. We did ok.’”

That’s part of why I keep a few photos of younger me in my office. To remember to step back from time to time to see how far I’ve come. To look at that kid and say, We’re doing alright. We’re doing alright.

There’s another reason too.

In Stillness is the Key, I wrote about inner child work—the practice of staying aware of the younger version of yourself that still lives inside you. When you’re hurt or betrayed or unexpectedly challenged, pay attention to how you react. Notice the “age” of that reaction. Is it mature, measured, proportional? Or does it feel more like a wounded eight-year-old lashing out?

That’s your inner child—the pain you still carry from early experiences, hijacking your adult mind.

The photos help me stay aware of him. To notice when he’s the one reacting instead of me. To take care of him rather than let him run the show.

11. “Sense of Urgency” Signs

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Preparation is important.

Planning is important.

Reflection is important.

I mean, I wrote a whole book on this because it’s true. 

At the same time, I put up two signs at The Daily Stoic offices and in the backstock of The Painted Porch that say, “Sense of Urgency.”

It’s something I cribbed from the kitchens of Thomas Keller, the creator of Per Se. He wanted his staff to understand that they weren’t waiting on customers…the customers were quite literally waiting for them. Sure, making great food takes time and it can’t be rushed…but it also can’t be slow-walked.

There is an old Latin expression that I think captures the balance here nicely: Festina lente. Make haste slowly. A sense of urgency…with a purpose. Energy plus moderation. Measured exertion. Eagerness, with control. 

That, to me, is what the “Sense of Urgency” sign is a reminder of—it’s about getting things done, properly and consistently.

12. Chunk of an Old Tombstone

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I’ve talked before about the Memento Mori coin—I keep one on my desk and carry another in my pocket. On the front it has a rendering of Champaigne’s Still Life with a Skull painting. On the back, it has Marcus Aurelius’s quote: “You could leave life right now. Let that determine what you do and say and think.” Except I cut off the last part—as a reminder that there isn’t even time to go through the whole quote. 

I also have this chunk of an old Victorian tombstone. How it left that cemetery and came to be for sale, I don’t know and don’t want to know. 

But I know that it sobers me and sets me right each time I look at it. Because the piece had just one word on it. It says, “Dad.”

Somebody who so identified with that word they wanted it on their tombstone; who lived and died and whose gravestone eventually even fell into disrepair. Who were they? How did they pass? Are they missed? Were they famous? It doesn’t matter. They are gone now. Almost certainly, they were gone too soon. They left behind a family. They will never walk or speak or love or cry again. 

And so it will go for me. And so it will go for you. 

13. My Guiding Sentences

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On every project I do, I print out a notecard with a sentence or an admonition that captures the essence of what I am trying to achieve on that project. 

When I was working on Ego is the Enemy, I had this quote from Machiavelli on the wall to inspire its style and ethos: “I have not adorned this work with fine phrases, with swelling, pompous words, or with any of those blandishments or external ornaments with which many set forth and decorate their matter. For I have chosen either that nothing at all should bring it honor or that the variety of its material and the gravity of its subject matter alone should make it welcome.”

When I was working on the Stoic Virtues series, I had a quote from Martha Graham: “Never be afraid of the material. The material knows when you are frightened and will not help.” 

One from Boccaccio: “Who in our day can penetrate the hearts of the Ancients? Who can bring to light and life again minds long since removed in death? Who can elicit their meaning? A divine task that—not human! It is, therefore, my plan of interpretation first to write what I learn from the Ancients, and when they fail me, or I find them inexplicit, to set down my own opinion.” 

And one from Bob Johnson to Johnny Cash: “You need to build a mausoleum in your head with big iron doors so that nobody can get in there except you. You don’t let me in there, you don’t let June in there, you don’t let your manager in there, you don’t let the record company people in there. You have to decide for yourself what you want to do with your music and not let anyone else tell you.”

And for the project I am working on now, it’s a quote from Paul Horgan, a two-time Pulitzer Prize-winning biographer and historian: “Historical writing which is not literature is subject to oblivion.”

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I have all these reminders because I need them.

On the Daily Stoic podcast, I once asked Pau Gasol—two-time NBA champion, six-time All-Star—about the role these kinds of reminders play in sports. 

“Athletes appreciate pointers and directions,” he said. He mentioned the famous mantra displayed throughout the San Antonio Spurs facilities: Pound the rock. “That was a big one…Just keep pounding the rock. If you hit it a thousand times or two thousand times, you might not see a crack, but it’s that next hit, that next pound where the rock will crack. You just got to keep at it, keep at it, keep at it.”

Reminders matter. They make you better. They keep you centered. If life were easy, if we were perfect, we wouldn’t need them. But it isn’t, and we aren’t. Things get complicated. Things go awry. We get mixed signals and we get overwhelmed and we get knocked off course. In those moments, it helps to have a good reminder to fall back on.

So whatever form these things take for you—a sign, a notecard, a print, a picture, a quote on the wall, a pine cone on your desk—surround yourself with things that mean something to you. Tattoo your walls with precepts. Fill your shelves with totems. Put good advice on and around your desk.

It will make you better. 

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May 20, 2026by Ryan Holiday
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