Running 50 Kilometers Through Rome To Understand Stoicism

Come along with Ryan as he sets out to run farther than he ever has before: 50 kilometers through Rome, past some of the most important Stoic sites in the world. 🎥 WATCH RYAN RUN THE STOIC 50K https://www.youtube.com/watch?v=R2LNSVXbsaI: https://www.youtube.com/watch?v=R2LNSVXbsaI 🎟️ DAILY STOIC LIVE https://www.dailystoiclive.com/| Ryan Holiday is coming to a city near you https://www.dailystoiclive.com/! Grab tickets here https://www.dailystoiclive.com/ | https://www.dailystoiclive.com/ 🎙️ AD-FREE https://dailystoic.supercast.com/| Support the podcast and go deeper into Stoicism by subscribing to The Daily Stoic Premium https://dailystoic.supercast.com/ - unlock ad-free listening, early access, and bonus content: https://dailystoic.supercast.com/ https://dailystoic.supercast.com/ ✉️ FREE STOIC WISDOM https://dailystoic.com/dailyemail | Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemail https://dailystoic.com/dailyemail -- Stop online threats before they become real-world attacks. Visit ironwall.com/DAILYSTOIC and request a free Risk Assessment to see exactly how exposed your executives are. -- Wealthfront’s high-yield cash account: https://www.wealthfront.com/stoic This experience may not be representative of other Wealthfront clients, and there is no guarantee of future performance or success. Experiences will vary. Ryan Holiday, who’s a client of Wealthfront, receives cash compensation from Wealthfront Brokerage for paid testimonials in his podcast, creating a conflict of interest. More details available via the referral link. The Direct Deposit Plus Investing Program from Wealthfront Advisers LLC and Wealthfront Brokerage LLC provides eligible clients a 0.25% APY increase above the base APY on eligible Cash Account balances (up to an overall boosted rate of 4.30% for a limited time when including the three month 0.75% APY boost for new clients) when you direct deposit $1,000 a month, plus open, fund, and maintain an investing account. Wealthfront may change or end the program at any time and determine eligibility at its discretion. Terms apply. Full details at wealthfront.com/promo-terms. The Cash Account, which is not a deposit account, is offered by Wealthfront Brokerage LLC ("Wealthfront Brokerage"), Member FINRA/SIPC. Wealthfront Brokerage is not a bank. The Annual Percentage Yield ("APY") on cash deposits as of January 30, 2026, is representative, requires no minimum, and may change at any time. References to the APY for the Wealthfront Cash Account, including any APY increase, are to the APY paid by insured depository institutions that participate in our cash sweep program (the "Program Banks”). Wealthfront Brokerage does not pay interest. Wealthfront Brokerage sweeps cash balances to Program Banks, where they earn the variable APY. Instant and same-day withdrawals use the Real-Time Payments (RTP) network or FedNow service. Transfers may be limited by your receiving institution, daily caps, or participating entities. New Cash Account deposits have a 2–4 day hold before transfer. Wealthfront does not charge fees for these services, but receiving institutions may impose an RTP or FedNow Fee. Processing times may vary.. Fees & Eligibility requirements may apply to certain checking features. Investment advisory services are provided by Wealthfront Advisers LLC, an SEC-registered investment adviser. Investing involves risk, including the possible loss of principal. Securities investments are not bank deposits, bank-guaranteed or FDIC-insured, and may lose value. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Ryan Holiday?

  Welcome to the Daily Stoic Podcast, designed to help bring those four key Stoic virtues: courage, discipline, justice, and wisdom into the real world.

• 0:17Ryan Holiday?

  I'm gonna run the furthest I've ever run in my life. I'm gonna run 50 kilometers through the streets of Rome, the eternal city. And I'm gonna pass some of the most important Stoic sites in the world as I do it. But why? That's the question. Why? Why am I gonna run 50K? Because it's hard. That's the whole point. The Stoics said that doing hard things was good for you.

• 0:43Ryan Holiday?

  I learned about this great thing from Jesse Itzler. It's this idea of a "mishogi." You pick something hard you do every year, something really hard, something that doesn't matter how the rest of the year goes. You look back and you remember that's the year that you did that, that you climbed the tallest mountain in your country, that you that you lost a certain amount of weight, that you you put in a certain amount of volunteer hours, or you ran a marathon. I'm doing one right now. I'm doing a 50K in Rome to all the different Stoic sites. And look, it doesn't matter how it ultimately ends up going, because I got better for trying. That's the point of the mishogi thing. If you succeed or you don't succeed, it's that you went after it and you were better for wrestling with this thing.

• 1:27Ryan Holiday?

  It has to be a stretch. It has to be outside your normal limits. It has to be beyond your capacities. Because if it isn't, you're not gonna remember it. It's not gonna mean anything. So you wanna pick something that's big, that's ambitious, that scares you a little bit. And this thing scares the shit out of me. So last year, I did the original marathon in Greece in July by myself, and also in the middle of a heatwave. And I remember I just I hit this wall. One of the things you learn when you when you sort of hit a wall is that you just keep going. You have you have more in you than than than you think.

• 2:10Ryan Holiday?

  And I'm not looking forward to hitting that wall again today, but that's one of the things you learn, how you how you push past that. I've never done this distance before. The what I did last summer in Greece was was the closest. That's like 30. This will be 31-plus miles. I've not run on cobblestones like this before. But one of my one of my favorite quotes from Marcus Aurelius, he says, "Not to think it's impossible just because it's hard, but to understand that if it's humanly possible, you can do it also." I know physically, people can do this. I know plenty of people who have done this and further.

• 2:54Ryan Holiday?

  Also, what they say about ultra-running is that it's basically a math equation. If you've done the training, if you have the calories, if you have the willpower, if you have the water, the body can do it. That's not the question. It's do you have the willpower, the fortitude? Do you have the commitment? Do you want it bad enough? That's what it takes. So I know it's possible. I know it's possible for me to do it. So now it's just a question. And this is ultimately what Stoicism is, is am I going to do it? Or am I gonna quit somewhere along the way? And look, by the way, sometimes that's the prudent thing to do, too. You're hurt, it's dangerous, whatever. So sometimes you have to make a call like that.

• 3:37Ryan Holiday?

  But but I know that the part of this that really matters, ultimately, when it boils down to it, the part of it that really matters is in my control, whether I'm gonna keep going or not. And then there's the other factors that are not in my control. You prepare for those as much as you can, but you gotta take it as it goes, and we're gonna do it.

• 4:02Ryan Holiday?

  So Marcus Aurelius was buried in there. This is known as Hadrian's Tomb. But I think, fittingly, after Marcus and Antoninus and Hadrian are buried there, it becomes a castle. It's a castle here on the Tiber River protecting Rome from invasion. It becomes a citadel, which is actually one of the most powerful images in Stoic philosophy, the idea of the inner citadel. Yeah, it's great to have fortresses like this, but the real fortress has to be inside, right? The toughness inside, the thing you retreat to, the thing that protects you. And and when we do hard things, when we train, when we push ourselves physically, that's what we're doing. We're reinforcing, we are building that inner citadel. And that that inner citadel is what you draw on, that inner reservoir of strength, what Thomas Paine said of George Washington, that it was this cabinet of fortitude.

• 4:45Ryan Holiday?

  That's what protects us from the things that are happening outside. That's what we draw on when things are really hard. So when we're doing hard things, that's what we're doing. We're developing that inner citadel.

• 5:06Ryan Holiday?

  Look, do we do hard things because we wanna impress people? Do we do hard things because we wanna beat other people? Do we do hard things because we want trophies? No, that is not why. Behind me is one of the great trophies of history. It's Marcus Aurelius's victory column. It's what they put up in honor of his victories in the Marko Manic War. 400 feet of carvings. It stretches almost 200 feet in the air. It's a towering feat of accomplishment, literally carved in stone. You know what? He wasn't around to enjoy it. He died before it finished. And then in the 15th century, a pope knocked him off and put Saint Paul up on top. And they put a new inscription at the bottom, and they wrongly attributed the victory to someone else, which is the point.

• 5:51Ryan Holiday?

  Trophies are not for you. You do hard things because doing hard things is good for you. The benefit is baked in in having done them. That's why I like doing challenges like this, not races, not competitions. I like doing challenges where the victory is what I get out of it.

• 6:18Ryan Holiday?

  All right, so here we have the Trevi Fountain. The Trevi Fountain has been fed for over 2,000 years by the Virgo Aqueduct. What does this have to do with Stoicism or doing hard things? It's just a pretty little fountain like that? No. Actually, Seneca would throw himself in the Virgo Aqueduct once a year. He says, "I've accustomed myself to this kind of thing." He says that. "I seek out the hardships, I seek out the challenges, throw myself in the cold water." Now, if you're running, you're doing any kind of sports, you know, there's supposedly some benefits from some sort of cold exposure, cold therapy, you know, inflammation. Your immune system helps you recover and all of that. That's not why Seneca did it. That's not why we do hard things. We do hard things because we are building the muscle to be able to do hard things.

• 7:02Ryan Holiday?

  Seneca talks about how we treat the body rigorously so that it's not disobedient to the mind. Throwing yourself in cold water, in that freezing water, is the perfect metaphor for that. It's not fun while you're doing it, but you're glad you did it after.

• 7:19Ryan Holiday?

  So the great line about this statue from the Soviet dissident, Joseph Brodsky, he walked up here one early morning, and he said, "If Marcus Aurelius's antiquity, it is we who are the ruins." I think he's just sort of marveling at this great man who 2,000 years ago, in the pages of his journal, he was writing notes to himself about controlling his temper, about getting up early, quenching his desires, his urges, about being kind to people, about working hard. And he says, "Fight to be the person that philosophy tried to make you." He didn't wanna be imperialized.

• 8:00Ryan Holiday?

  He didn't wanna be stained purple by all the accoutrement of power, the sycophants around him, people worshiping him as a god. He wanted to be good. He wanted to be decent, which is ultimately like the hardest thing to do in the world, especially when you are the most powerful person in the world. I love I love the statue. It's worth a run anytime you're in Rome. You come up these big gradual steps, and then suddenly, you're you're at the top. There's also a quirk. This statue, that's not the original. The original's inside the Capitoline Museum right there, but it's a quirk of history that it even survived. The Christians, who had good reason not to like Marcus Aurelius,

• 8:45Ryan Holiday?

  they would have destroyed this had they known. They thought it was Constantine, the first Christian emperor, so they didn't destroy it, so they kept it. So there were something like 25 equestrian statues in antiquity that we know of. All of them are gone, except for this one. This one endures. And it's totally by accident. There's a little bit of gallows humor in this, too, because I still have the furthest that I've ever run to go. There's a Stoic named Agrippinus, who's banished from Rome by the emperor for running afoul of him. He's banished by Nero. And when he's told he's gonna he's gonna have to leave, he just says, "Okay, we'll have lunch on the road." So that's kind of Stoicism, is like,

• 9:28Ryan Holiday?

  you take it all with a shrug or a smile, because what are you gonna do?

• 9:44Ryan Holiday?

  You gotta be prepared for things to go wrong. And they just did. I just got lost. I did a one-mile loop in the wrong direction. I not only knew something like this would happen, I figured it would happen right here. When we do hard things, we are prepared for them to be harder than even than we are anticipating. It's like Eisenhower said, how plans are worthless, but planning is everything. For the Stoics, if you're like, this is all the gas I have in the tank. This is all I'm capable of doing. I need everything to go right. You're in a real vulnerable position. But if you're ready for everything to go wrong, everything to go sideways, well, you'll be pleasantly surprised when that doesn't happen. And you won't be unpleasantly surprised if it does happen. That's what Seneca was saying, that the unexpected blow lands heaviest. If I was lost and disoriented and mad at myself right now, this would be harder than it is. But it's not so bad.

• 10:27Ryan Holiday?

  I just gotta go down here, go here, and we'll be good to go.

• 10:39Ryan Holiday?

  So one thing we know about the Stoics is that they hated the Colosseum. They hated the violence. They hated the mob mentality of it. They hated the brutality, the mindlessness of it. Seneca talks about how degrading and gory and disgusting what happened on the floor of the Colosseum was, Marcus Aurelius supposedly wouldn't read his philosophy or write in Meditations in his box. He was obligated to be there for work, but he didn't like it. That's not to say that they didn't understand the power of a good sports metaphor. Marcus Aurelius said, "Life isn't a dance. It's more like a wrestling match. You have to be dug in and ready for sudden attacks." And in other passages in Meditations, he talks about being like those gladiators

• 11:20Ryan Holiday?

  who are torn apart, bloody, begging to come back the next day. He didn't actually mean that as a positive. He meant like they needed to change. That life was telling them something. It was beating them up. It was destroying them, and they weren't going in the right direction. The point is, I think they would have liked Theodore Roosevelt's idea of the man in the arena. They didn't actually like the arena, but they liked being the man in the arena. They understood that life was tough, that life was difficult, that it was always challenging us.

• 11:57Ryan Holiday?

  So this is Circus Maximus. The Colosseum is obviously what people think of when they think of Rome. But this is where the sports happened. This was the center of Roman athletic life. Something like 250,000 spectators could fit in here. These chariots would come zipping and zipping, zipping by. And one of the most powerful images in the Stoic virtues comes from here, from Circus Maximus. The idea of Sophocene, the chariot racer. Sometimes you're pulling the horse back, reining him in. Sometimes you're getting him to go faster and faster and faster. And then the art of steering this rickety chariot, trying to make the tight turns. It's an incredibly difficult sport. And so the image of the charioteer was emblematic for the Stoics

• 12:39Ryan Holiday?

  of the art of the good life, of temperance, of moderation, of Sophocene, which, you know, any kind of challenge requires of you. You have to train, but you can't train too hard. Overtraining causes injury. You can't push yourself too hard. You have to pace yourself to be able to hit your marks, your benchmarks, all of which I'm thinking about right now. And now I get to run a little bit on the actual track because you can come down and do it, which is pretty incredible.

• 13:10Ryan Holiday?

  All right, now the pavers on the Appian Way start. These are rough, man. But it's hard to complain about the fact that you're running on a road that is thousands of years old. The stones have been here so long, they have grooves of wagon wheels in them.

• 13:31Ryan Holiday?

  That could have been from Marcus Aurelius. Could have been from every emperor ever. Could have been Seneca. Could have been Epictetus. Look, these stones were also worn down by Allied Jeeps and tanks. And they retook Italy, town by town. And then, you know, here we go. We get to run along them ourselves. It's still here.

• 13:59Ryan Holiday?

  Kind of gives you the sense that Marcus Aurelius talked about, just the rhythms of history. Just one generation leading seamlessly into the next, one after another.

• 14:16Ryan Holiday?

  Somewhere around here, I have a vague sense memory of it. I was riding my bike with my wife along the Appian Way. We pulled over on the side. I hadn't planned it. We're just hanging out. Been together a long time, and I just, I just said, hey,

• 14:30Ryan Holiday?

  you think we should get married at some point? This isn't a formal ask, but are you seeing this go the same direction I am? And we've been married 11 years now. You know, when we talk about doing hard things, when we talk about courage, it's not just physical stuff, but also the moral courage to put yourself out there. Most of the things you want in life, most of the good things in your life, the best things in your life are on the other side of some little bit of moral courage. It's like that movie where Matt Damon says, "All it takes is 20 seconds of courage, 20 seconds of insane bravery to change the course of your life." You know, it's the decision to walk across the room and say hi to someone. It's the decision to raise your hand and volunteer for something. It's the decision to hit publish on something.

• 15:14Ryan Holiday?

  It's the decision to go out for something, to ask for that promotion, to put your hat in the ring. It's the decision to tell someone that you love them, that you want to be with them. It's the decision, also the day-to-day-ness of sticking with it, even when it's hard, even when you go, what am I doing? Even when it's not totally what you imagined, right? There's the doing the hard things. There's the 20 seconds of insane bravery and commitment, the leap. Then there's also the day-to-day-ness of it. And I do think that's why exercise and physical challenges and, you know, doing big scary things is a great metaphor. All growth is a leap in the dark.

• 15:54Ryan Holiday?

  So supposedly, this is Seneca's tomb. We don't know for certain. It's got no inscriptions. And it's here on the Appian Way. I am almost 13 miles in, feeling pretty good. The last time I was here was, I don't know, almost 12, 13 years ago. One of my favorite lines from Seneca is, he talks about how he comes back to the house that he grew up at. And the trees are starting to die around it. And he wants to criticize the caretaker for not taking care of them. And the caretaker says, "What are you talking about? These trees were planted when you're born. They're dying because they're old." And this is when Seneca realizes that he's old, that we can see sometimes in nature the passing of time

• 16:38Ryan Holiday?

  that is invisible to us because we see ourselves in the mirror each day. I was looking at a picture of myself that I took here 12, 13 years ago, whenever I was here last. And, you know, I feel the same. I feel great. I feel better than I did then. But you look at it and you go, oh, there's more gray hairs. There's more wrinkles. You could see the last 10 years. I wouldn't say they've been hard, but they've been a lot. They've been a lot for all of us, right? And so sometimes coming back to a place that you've been is a really good reminder of that memento mori. There's another Stoic concept there, how we never step in the same river twice. But the point is, the river is passing us by. That Marcus Aurelius talks about time being this vicious, unrelenting, ceaseless, almost merciless flow of events, faster and faster and faster.

• 17:23Ryan Holiday?

  And it's taking us with us. So that's what I'm thinking about here at Seneca's tomb. I wonder if he knew that his plays would still be read 2,000 years later? I wonder if he knew that his grave would get worn down by events and eventually forgotten? I don't know. These are great Stoic things to think about here.

• 17:44Ryan Holiday?

  I am 15.64 in. So this is basically the turnaround point. I'm feeling pretty good. Feel hydrated. The shade has been nice. It's getting hot. I'm way behind schedule though. It's 8:40 already. So I'm already 3 hours and 40 minutes into this. I will say that the stopping and filming, I didn't quite budget for how much time this was going to take. But I got some really good advice from someone who did a run like this before. He said, "Just let it take however long it takes. You're not going to be glad you rushed through it." He said, "Take your time. Stop, admire the sights, soak it in. If you have to walk, you have to walk." The point isn't to win at your hobbies. The point is to do it, to have fun doing it, to experience it, to be there for it. You don't rush through other things that are pleasurable. And then for some reason, physical activity,

• 18:29Ryan Holiday?

  we try to get done as fast as possible. So almost 16 miles in, taking a little bit of a pause. And then I'm going to turn around and go back.

• 18:39Ryan Holiday?

  You know you're doing something crazy when you think only seven miles left. But that's where I am, seven miles left. But that's kind of the good thing. When you train, you push yourself.

• 18:52Ryan Holiday?

  You raise your threshold higher and higher

• 18:56Ryan Holiday?

  until what used to seem like a lot now only seems like a little. Marcus Aurelius talks about practice even what seems impossible. He talks about, you know, putting the reins of the horse in the opposite hands, getting practice, doing it the hard way, doing hard things. So then, when you are in the middle of a hard thing, things that you used to think were too hard, you actually look forward to.

• 19:29Ryan Holiday?

  I've officially done a marathon. So I have five-ish or so miles left. My final thought as I get through the home stretch is this idea from Epictetus. He says, you know, "Whatever difficulties you face, understand what resources you have inside you." Marcus Aurelius, maybe he was ripping on that exact passage. You would talk about this in Meditations. He's just like, what are you going to meet the problems of tomorrow with? It's the same thing you met the problems with yesterday with, the same weapons, the same tools. How am I going to get through the last six miles? I mean, the same willpower and strength and training that I got through the first 26 miles. And honestly, this is my favorite part.

• 20:11Ryan Holiday?

  First off, because, you know, they say it's not really pushing yourself until you get to your limits. It's really after you get tired and that point that you keep going. That's where the sort of the muscle and the strength and the fortitude is earned. But like when I'm working on a book, it's like the first two-thirds, I say, even the first, you know, 80% of it, that's the really hard part. But it's the last 20%, it's the last third, when it's downhill, when you know that you're going to make it as long as you don't quit. Like, you now know that you're operating under some momentum. You've crossed most of the difficulties off. Now it's just, like, some people say, you know, the last 10% takes 40% out of you. And that's true.

• 20:55Ryan Holiday?

  But I also think you're in a rhythm. You have this sense of what you're capable of because of what you've just done. And you just got to see it through, which is where I got to go now.

• 21:12Ryan Holiday?

  Well, I did. Just barely. I was fucking dying at the end. That was a limp across the finish line. I'll tell you what, the limit is about 29.

• 21:31Ryan Holiday?

  The limit's about 30. Exactly 29 and a half. That's where I lost it. You know, they say it always takes longer than you expect, even when you take this law into account. I don't, I mean, it took much longer than I thought. So it is much harder than I thought. Thus, the intersection of it all. My son ran the last quarter mile with me, which is just the fucking best. And I think I asked my wife if she wanted to get married somewhere along the Appian Way. And then all these years later, I'm finishing a run on, partly on that road.

• 22:16Ryan Holiday?

  My son is finishing with me.

• 22:20Ryan Holiday?

  I'm a very lucky person. And now I have a slightly better sense of what I'm capable of and what I got in the tank.

• 22:31Ryan Holiday?

  And now, now I got to rest.

• 22:37Ryan Holiday?

  Hey, Sam. Dying.

• 22:40Speaker 01

  Yeah. How did this take six and a half hours?

• 22:44Ryan Holiday?

  Well, that's not a very nice question, is it?