The Daily Stoic - Running 50 Kilometers Through Rome To Understand Stoicism

Episode Date: September 13, 2026

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🎟️ DAILY STOIC LIVE | Ryan Holiday is coming to a city near you! Grab tickets here |  https://www.dailystoiclive.com/🎙️ AD-FREE | Support the podcast and go deeper into Stoicism by subscribing to The Daily Stoic Premium - unlock ad-free listening, early access, and bonus content: https://dailystoic.supercast.com/✉️ FREE STOIC WISDOM | Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at 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/stoicThis 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.

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Starting point is 00:00:00 Welcome to the Daily Stoic podcast, designed to help bring those four key stoic virtues, courage, discipline, justice, and wisdom into the real world. I'm going to run the furthest I've ever run in my life. I'm going to run 50 kilometers through the streets of Rome, the eternal city. I'm going to pass some of the most important stoic sites in the world as I do it. But why? That's the question. Why?
Starting point is 00:00:32 Why am I going to run 50K? Because it's hard. That's the whole point. The Stoics said that doing hard things was good for you. I learned about this great thing from Jesse Itzler, 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 lost a certain amount of weight, that you put in a certain amount of volunteer hours, or you ran a marathon.
Starting point is 00:01:08 I'm doing one right now. I'm doing 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 Meshogi 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. 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 going to remember it. It's not going to mean anything. So you want to pick something that's big, that's ambitious, that scares you a little bit.
Starting point is 00:01:43 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 heat wave. I remember I just, I hit this wall. One of the things you learn when you sort of hit a wall is that you just keep going. You have more in you than you think. And I'm not looking forward to hitting that wall again today, but that's one of the things you learn how you push past that. I've never done this distance before.
Starting point is 00:02:21 What I did last summer in Greece was the closest. This will be 31 plus miles. I've not run on cobblestones like this before, But one of my favorite quotes from Marcus Realist, 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. 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 cal, if you have the cal,
Starting point is 00:03:03 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 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 am I going to do it or? Am I going to 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. It's dangerous. So sometimes you have to make a call like that. But I know that the part of this that really matters,
Starting point is 00:03:40 ultimately when it boils down to it, the part of it that really matters is in my control, whether I'm going to 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 got to take it as it goes, and we're going to do it. So Marcus was buried in there. This is known as Hadrian's tomb.
Starting point is 00:04:06 But I think fittingly, after Marcus and Antoninus and Hadrian are buried there, There comes 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.
Starting point is 00:04:22 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 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.
Starting point is 00:04:37 And that inner citadel is what you draw, that inner reservoir of strength, what Thomas Payne said of George Washington, then it was this cabinet of fortitude. 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.
Starting point is 00:04:53 We're developing that inner citadel. Look, do we do hard things because we want to impress people? Do we do hard things because we want to 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' victory column. It's what they put up in honor of his victories in the Marco Manic War.
Starting point is 00:05:25 It's 400 feet of carvings. It stretches almost 200 feet in the air. It's a towering feat of accomplishments, 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 St. 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.
Starting point is 00:05:51 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. Alright so here we have the Trevi Fountain. The Trevi fountain has been fed for over 2,000 years by the Burville Aquac. What does this have to do with Stoicism or doing hard things? It's just a pretty little fountain you look at. No. Actually Seneca would grow himself in the Virgo aqueduct once a year. He says, I've accustomed to get myself
Starting point is 00:06:35 to this kind of thing. This is that I seek out the hard to seek out the challenges to throw himself in the cold life. Now, if you're a runner, you do any kind of sports, you know, there's supposedly some benefits from sort of cold exposure and cold therapy, you know, inflammation,
Starting point is 00:06:51 your immune system helps you recover it and all of that. That's not why Seneca did. 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. Seneca talks about how we treat the body vigorously so that it's not disobedient to the mind. Throwing yourself in cold water
Starting point is 00:07:10 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. 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' antiquity, it is we who are the ruins.
Starting point is 00:07:32 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 want to be imperialized. He didn't want to be stained purple by all the accoutrement of power, the sycophants around him, people
Starting point is 00:08:08 worshipping 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 at the top. There's also a quirk. This statue, that's not the original. The originals inside the Capitoline Museum right there, but it's a quirk of history that it even survived. The Christians had good reason not to like Marcus realists. They would have destroyed this that they known. They thought it was Constantine, the first Christian emperor,
Starting point is 00:08:50 so they didn't destroy it, so they kept it. So there was 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.
Starting point is 00:09:11 There's a stoke name of Griponis, who's banished from Rome by the emperor for running a fallow and was banished by Nero. And when he's told he's going to have to leave, he just says, okay, we'll have her lunch on the road. So that's kind of stoicism is like you take it all with a shrug or a smile because what are you going to do? Every time you look at your phone, there's another chaotic headline.
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Starting point is 00:12:18 stoic. You got to 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 incapable 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
Starting point is 00:12:54 Seneca was saying that the unexpected blow lands heaviest. If I was law, and disoriented and mad at myself right now, this would be harder than it is. But it's not so bad. I just gotta go down here, go here, and we'll be good to go. So one thing we know about the Stoics is that they hated the Coliseum.
Starting point is 00:13:19 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 Coliseum was Markets really supposedly would read his philosophy or write in Medi-Denet. Asians in his box. He was obligated to be there for work, but he didn't like it.
Starting point is 00:13:40 That's not to say that they didn't understand the power of a good sports metaphor. Marks Rueh said life isn't a dance. It's more like a wrestling match. You have to be dug in and ready for sudden attacks. In another passage of meditations, he talks about being like those gladiators 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. They were, that life was telling them something. It was, 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
Starting point is 00:14:14 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. 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.
Starting point is 00:14:40 This was the center of Roman athletics. of Roman athletic life. Something like 250,000 spectators could fit in here. These chariots would come zipping and zipping by. And one of the most powerful images in the Stoic Virtues comes from here, from Circus Maximus. The idea of Sophrasine, the chariot racer,
Starting point is 00:14:58 sometimes you're pulling the horse back, reining them in, sometimes you're getting them 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. So the image of the charioteer was emblematic for the stoics of the art of the good life of temperance, of moderation of Safrasine, which, you know, any kind of challenge requires of you. You have to train, but you can't train too hard. Over-training causes injury.
Starting point is 00:15:26 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. 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.
Starting point is 00:16:06 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.
Starting point is 00:16:34 Kind of gives you the sense that Marcus really talked about just the rhythms of history, just one generation leading seamlessly into the next one after another. Somewhere around here I have a vague sense memory of it. I was riding my bike with my wife along the Appian Way. I pulled over on the side. I hadn't planned it. We're just hanging out. I've been together a long time and I just said,
Starting point is 00:17:04 hey, you think we should get married at some point? This isn't a formal ass, 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. 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.
Starting point is 00:17:44 It's the decision to raise your hand and volunteer for something. It's the decision to hit publish on something. 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-dayness of sticking with it, even when it's hard, even when you go, what am I doing?
Starting point is 00:18:04 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 to leap. Then there's also the day-to-dayness of it. And I do think that's why, exercise and physical challenges and you know doing big scary things is is a great metaphor all growth is a leap in the dark 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
Starting point is 00:18:38 almost 13 miles in feeling pretty good the last time I was here was I 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 him. And the caretaker says, what are you talking about? These trees were planted when you're born. They're dying because they're old.
Starting point is 00:19:06 And this is when Seneca realizes that he's old, that we can see sometimes in nature the passing of time 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 momentum more. There's another stow concept there, how we never step in the same river twice.
Starting point is 00:19:49 The point is the river is passing us by that Mark Smith talks about time being this vicious, unrelenting, ceaseless, almost merciless flow of events faster and faster and faster, 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.
Starting point is 00:20:17 I am 15.6 for in. So this is basically the turnaround point. I'm feeling pretty good. Feel hydrated. The shade has been nice. I'm way behind scheduled. I'm just 840 already. So I'm already three hours and 40 minutes into this. I will say that the stopping and filming I didn't quite budget for how much time this is 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. 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. 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 gonna turn around and go back. You know you're doing something crazy when when you think only seven miles left. but that's where I am, seven miles life.
Starting point is 00:21:22 But that's kind of the good thing. When you train, you push yourself, you raise your threshold higher and higher until what used to seem like a lot, now only seems like a little. Mark Shrews talks about practice, even what seems impossible. He talks about putting the reins of the horse
Starting point is 00:21:45 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, they actually look forward to. 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
Starting point is 00:22:15 is this idea from Epic Genus, he says, whatever difficulties you face understand what resources you have inside you. Marks really, maybe he was ripping on that exact passage, talk about this in meditation, this is 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. First off, because,
Starting point is 00:22:47 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 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.
Starting point is 00:23:16 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, but I also think you're in a rhythm, you have this sense of what you're capable because of what you've just done, and you just gotta see it through,
Starting point is 00:23:38 which is where I gotta go now. Well, I did it, just barely. I was fucking dying at the end. That was a limp across the finish, then I'll tell you what. The limit is about 29. 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,
Starting point is 00:24:21 even when you take this law into account. I don't, I mean, it took much longer than I thought, so it is much hotter than I thought, thus the intersection of it all. My son ran the last quarter of, quarter mile with me, which is just the fucking best. I think I asked my wife if she wanted to get married somewhere along the Appian Way and then all these years later,
Starting point is 00:24:47 I'm finishing a run on, partly on that road. My son is finishing with me. 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. And now, uh, now I got a rest. Hey Sam, you die. Yeah.
Starting point is 00:25:16 How does this take six and a half hours? Well, that's not a very nice question, is it?

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