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RyanHoliday.net - Meditations on strategy and life
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This Is Always Worth All The Trouble (Or So I Tell Myself)

There are a million good reasons not to travel.

I woke up with a bunch of them this morning. 

I was exhausted. My kids were fighting. My wife has been sick. It was ungodly hot—literally the hottest Europe has ever been. My routine is out the window. So is any sense of a budget. Our suitcases are already full of knick-nacks and crap we don’t need and there’s quite a bit of trip left. The car that was supposed to pick us up for our tour is late. 

But we’re in Rome. 

It’s all worth it…or so I tell myself.

Even though travel can be expensive, stressful, and frustrating. Even though it tests your patience. Even though things go wrong. Even though you know that when you get home, you’ll be behind on everything.

Still, it’s worth it. 

It has always been worth it.  

For all their warnings against escapism, the Stoics traveled widely—in an age when travel was far slower, harder, and more dangerous. 

Unlike his stepfather Antoninus, who never left Italy, Marcus Aurelius was on the road a lot as emperor. It wasn’t always pleasant. But it undoubtedly influenced his philosophy and his view of the world. He could have sent someone else to inspect the troops on his behalf, but he chose to go. When the calls of duty and the road converged, he went. Seneca was born in Corduba, Spain (modern Córdoba), moved to Rome, and in addition to his exile in Corsica, lived for nearly a decade in Egypt. Posidonius (a key figure in Middle Stoicism) worked and lived in many places throughout his long life—Syria, Athens, Rome, and Rhodes—and traveled almost the entirety of the known world. After completing his studies under Posidonius, Athenodorus traveled widely as a lecturer, reaching Petra, Egypt, and other major Mediterranean cities before becoming young Octavian’s teacher in Apollonia, on the coast of modern Albania.

These were critical experiences for them. Then, and now, hitting the road was a source of wisdom. It shaped their philosophy. It enlarged their view of the world. It opened their eyes to new lands, new customs, new perspectives.

“Travel is fatal to prejudice, bigotry, and narrow-mindedness,” Mark Twain famously wrote, “and many of our people need it sorely on these accounts.” 

This was true of America in the 19th and 20th centuries, and it was true in Rome in the first century. Marcus Aurelius’ passages in Meditations which reference being a citizen of the world were almost certainly shaped by the people he met in Athens and Tarsus and Alexandria (and of course the people he met in Rome who had traveled there from far away). 

Every culture thinks its norms are, well, normal. One of my favorite examples of this is the criticism I get that by talking about politics I am “upsetting half my audience.” It’s the most American thing in the world to assume that the world is as evenly divided as America is. (Shocker, it’s not!) 

Only travel can shake us from this ethnocentrism, awakening us to the plain fact that our way of life is but one of many. In our travels, we meet people who care about different things, wear different clothes, tell different stories, eat different foods, speak different languages. 

When he traveled, Montaigne sucked up everything he saw like a vacuum, avoiding much in the way of plans, leaving himself open to chance encounters and experiences. Like the time he came across men leading two ostriches on leashes as a present for a duke. He stopped in at every church he could find, taking in their various practices like an anthropologist.

When the New World was discovered—basically in his lifetime—Montaigne did not think the people who lived there were savages. From his travels, he understood that every distant land has its own culture and beliefs—and that our customs would seem just as barbaric to them. Not that he defended the “horrible barbarity” of cannibalism. What struck him was that “while judging correctly of their wrong-doings we should be so blind to our own.” Did the cannibals draw and quarter each other? Commit atrocities? Accuse each other of black magic? Who was actually the barbarian?

Perhaps it was a lesson he first absorbed from his extensive reading of Herodotus, our first great historian and travel writer, who traveled thousands over the course of his life—from Persia to Athens to Italy, Libya, Babylonia, Byzantium, and the Black Sea. Above all, he delighted in getting inside the nomos of each place—the people’s customs, and the ways they differed from his own. He loved to tell the story about a small sect in India that ate a small piece of their dead as part of a religious ritual. Obscene! Disgusting! But how did these people react when told that Greeks burned their dead at the funeral pyre? An outrage! A sacrilege!

Me and Herodotus in the Palazzo Massimo

The world is very big. The place you call home is only one small corner of it. There is wisdom on the other side of the hill, wisdom in the experiences that only the road can give you, wisdom in learning how other people live and why they live that way.

It’s easy to be comfortable where you are. To tell yourself that travel isn’t worth all the hassle. To think of it as a luxury, an indulgence, a needless extravagance. But it isn’t. It’s essential. “I was never a fan of people who don’t leave home,” the well-traveled Joan Didion once wrote. “It just seems like part of your duty in life.”

But leaving home doesn’t have to mean going far. It doesn’t have to mean spending lots of money on some exotic trip to the other side of the world. I remember talking to a waitress in Natchez, Mississippi once who told me she had never been to Vicksburg (a little over an hour away!). Growing up in the suburbs of Sacramento, I was lucky my parents took us on trips to Europe and China and Canada and Mexico, but I BARELY ever went to downtown Sacramento. Or even San Francisco. I only discovered the fullness of those cities as an adult. 

Don’t tell yourself you’ll do it later. When you’re older. When the kids are older. When things settle down. When you have more money. When it’s more convenient. That misses the point. You don’t need the benefits of travel someday, when your life is perfectly arranged for it. You need them now.

So hit the road! Travel to the well-known places and the little seen. Travel by boat and by car and by train and by plane and by foot. Read the signs. Struggle with the language barrier. See things from the other side of the road. Eat the food. Go to the museums. Sit at sidewalk cafes. See the ancient hieroglyphs and notice graffiti on city streets. See the cemeteries. Visit the battlefields. Listen to people chatter. Learn. Explore. Be curious. Ask questions. Carry a notebook. Write down everything you see and feel and think.

See your own country as a tourist. Live abroad like a local. Every building, every person has a story. Think of what they witnessed. Think of who stood where you are standing. Think of what was here before any of this was here. Think of what people used to think here, what they were afraid of, what they hoped for, what they believed.

Let things go wrong (and they will!). These experiences teach as much as anything else. Last summer, I spent 27 days in Greece with my family, covering some 3,000 kilometers between Athens, Olympia, Ithaca, Delphi, Thermopylae, Mount Olympus, Marathon, and Cape Sounio. We were in a Chinese rental car that was far too big for tiny ancient streets. We got a flat tire at the top of Mount Olympus. I was stung by a jellyfish near Thermopylae. We bumped into friends I hadn’t seen since high school. We got ripped off. On the last day, a bee stung me in the back of the throat and I almost died. Oh, and somewhere in between there, I got myself a bad case of sunstroke. 

But that’s what travel is supposed to be. Travel is an adventure. Travel is pushing your limits. Travel is trying new things. Travel is learning that most problems can be solved, most setbacks can be survived, and most of what goes wrong can be figured out. 

You don’t have to be gone for long. You don’t have to spend a fortune. You don’t have to see the whole world to become a worldly person.

But you have to check out what’s on the other side of the hill a couple times.

You have to expose yourself to different places, different people, different perspectives.

You have to hit the road.

It will be disruptive. Your patience will be tested. Things will go wrong.

And it will all be worth it.

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July 2, 2026by Ryan Holiday
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39 (Or So) Lessons On The Way To 39

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
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This Is Something You Have To Get Good At

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. 

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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