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The Daily Stoic

13 Sep 2026 · 23m · 14 chapters

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Running 50 Kilometers Through Rome To Understand Stoicism

In short

A Daily Stoic episode where the host runs 50 km through Rome’s Stoic sites to practice Stoic endurance—building an “inner citadel” of fortitude by choosing an annual, scary hardship (mashogi). He argues hard challenges aren’t for trophies or impressing others; the benefit is in the struggle itself, and preparation plus accepting the unexpected is key.

Guests

No guests are interviewed. The host references authors and figures (e.g., Jesse Itzler; Marcus Aurelius; Seneca; Epictetus; Joseph Brodsky; Mark Cirillo; Theodore Roosevelt; Eisenhower; Joseph Brodsky; Mark Schroes; Mark Stavilius).

Key claims

Hard things reinforce the mind/body; inner resilience matters more than external outcomes; pacing and prudence include knowing when to stop; moral courage parallels physical courage.

Notable examples

Marathon in Greece during a heat wave; Hadrian’s Tomb/inner citadel; Marcus Aurelius’ victory column; Trevi Fountain and Seneca’s cold-water ritual; Circus Maximus charioteer metaphor; Colosseum aversion; Appian Way cobblestones; Seneca’s tomb; “man in the arena” framing; Eisenhower’s “plans worthless, planning everything.”

Written by AI. May contain mistakes.

Chapters

0:45

The Challenge of 50K in Rome

Exploration of running 50 kilometers in Rome to embrace Stoic principles.

“You pick something hard you do every year.”
2:11

Building the Inner Citadel

The significance of facing hard challenges to strengthen inner resolve.

“to hitting that wall again today, but that's one of the things you learn, how you push past that.”
4:25

The Purpose of Doing Hard Things

Understanding the intrinsic value of challenges beyond external rewards.

“The toughness inside, the thing you retreat to, the thing that protects you.”
6:00

Seneca and Cold Exposure

Seneca's practice of seeking hardships and its relevance to modern challenges.

“I like doing challenges where the victory is what I get out of it.”
7:20

Marcus Aurelius and Self-Discipline

Reflections on Marcus Aurelius' focus on self-discipline and goodness.

“from the Soviet dissident, Joseph Brodsky, he walked up here one early morning and he said, if Marcus Aurelius is antiquity, it is we who are the ruins.”
12:03

Preparing for the Unexpected

Discussing the Stoic philosophy of readiness for unforeseen challenges.

“You got to be prepared for things to go wrong.”
14:01

The Chariot Racer and Stoic Virtues

Learn how the imagery of a charioteer reflects Stoic virtues of life.

“They didn't actually like the arena, but they liked being the man in the arena.”
15:07

Running on Ancient Roads

Explore the significance of running on the historic Appian Way.

“You have to pace yourself to be able to hit your marks, your benchmarks, all of which I'm thinking about right now.”
16:14

Moral Courage in Life Decisions

Discover the importance of moral courage in achieving life's goals.

“Kind of gives you the sense that Marcus really has talked about.”
17:38

Reflections at Seneca's Tomb

Reflect on how time and aging influence our perspectives on life.

“It's the decision to tell someone that you love them, that you want to be with them.”
Show all 14 chapters
19:35

Embracing the Journey

Understand the value of taking time to enjoy physical challenges.

“Mark Schroes 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.”
20:56

The Strength of Perseverance

Learn about the importance of perseverance in overcoming challenges.

“You know you're doing something crazy when you think only seven miles left.”
22:21

Crossing the Finish Line

Celebrate the emotional and physical journey of completing a marathon.

“I mean, the same willpower and strength and training that I got through the first 26 miles.”
23:41

Reflection on Accomplishments

Reflect on achievements and understanding personal limits after a marathon.

“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.”
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Transcript

Automatic transcript. May contain errors.

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 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? 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.

0:43Ryan Holiday: I learned about this great thing from Jesse Itzler. It's this idea of a mashogi. 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. 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.

1:19Ryan Holiday: 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 go pick something that's big that's ambitious that that scares you a little bit and this 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 hit this wall.

1:58Ryan Holiday: 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. 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 Trimelius, 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. though.

2:47Ryan Holiday: 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 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?

3:27Ryan Holiday: 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, whatever. So sometimes you have to make a call like that. 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.

4:02So 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,

4:12Ryan Holiday: 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 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 inner citadel is what you draw on, that inner reservoir of strength.

4:41Ryan Holiday: What Thomas Paine said of George Washington, that 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. We're developing that inner citadel.

5:06Look, 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 Wars. It's 400 feet of carvings. It stretches almost 200 feet in the air. It's a towering feat of accomplishment, literally carved in stone.

5:35Ryan Holiday: 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. 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.

6:17All right, so here we have the Trevi Fountain. The Trevi Fountain has been fed for over 2 ,000 years by the Murrville Aquinas. What does this have to do with stoicism or doing hard things? It was just a pretty little fountain to look at. No. Actually, Seneca would throw himself in the Virgo Octoduct once a year. He says, I've accustomed myself to this kind of thing. He says, I seek out the hardships. I seek out the challenges. Throw himself in the cold water. Now, if you're a runner, you do any kind of sports, you know, there's supposedly some benefits from cold exposure and cold therapy. You know, inflammation.

6:51Your 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 muscle to be able to do hard things. 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. 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 is antiquity, it is we who are the ruins.

7:32I 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. 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 accoutrements 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 the hardest thing to do in the world, especially when you are the most powerful person in the world.

8:18I love this 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 original is inside the Capitoline Museum right there, but it's a quirk of history that had even survived. The Christians, who had good reason not to like Marcus Trillius, 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 So there was something like 25 equestrian statues in antiquity that we know of. All of them are gone except for this one.

8:59This 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. was banished by Nero.

9:19Ryan Holiday: And when he's told he's going to have to leave, he just says, okay, we'll have lunch on the road. So that's kind of stoicism is like, he'd take it all with a shrug or a smile because what are you going to do?

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10:18Ryan Holiday: just your normal meeting with superpowers. And meanwhile, you get to actually listen instead of frantically typing up every word. Granola has been something we've used at staff meetings. They help people contribute better, track what's going on, and it captures the good ideas so we don't lose them. That was the point of the meeting, right? If meetings are eating up your day, granola is a no-brainer and you can try it totally for free. Just head over to granola.ai slash Daily Stoic and get a little bit of your time back. Granola dot AI slash Daily Stoic. Man, it has been insanely hot here in Texas.

10:51Ryan Holiday: I got in my truck yesterday. It said it was 115 degrees. I've been having to wait till like 830 at night to even walk the dog. It's been crazy. And I noticed when I'm not hydrated, it affects like everything, my energy, focus, my speeds when I'm running, my riding ability. Well, Instant Hydration is a premium electrolyte drink mix designed to support hydration, energy, recovery, focus, and overall performance without sugar or unnecessary additives. I've been on planes a lot for this daily stoic tour. And one of the things I do is I throw one of those into my water bottle or into the water that keep me on the plane even to not get dehydrated, which by the way, helps with jet lag.

11:31Ryan Holiday: They also have this great new icy flavor that tastes like you're having a slurpee or whatever. It's not overly sweet or salty. It's super easy to drink. Instant Hydration is made to be an electrolyte drink you can enjoy every day, not just after intense exercise. For a better way to stay hydrated, go to instanthydration.com slash stoic and use promo code stoic for over 40 % off your first subscription order. It's Instant Hydration's best offer available. That's instanthydration.com slash stoic promo code 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.

12:09I 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.

12:38That'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. I just got to go down here, go here, and we'll be good to go.

12:58So 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. as Mark Cirillo supposedly would 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. Mark Cirillo said, life isn't a dance. It's more like a wrestling match. You have to be dug in and ready for sudden attacks.

13:35In 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. 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.

14:17So 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 and zipping by. And one of the most powerful images in the Stoic Virtues comes from here, from Circus Maximus. The idea of sofrasine, 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.

14:55And so the image of the charioteer was emblematic for the Stoics of the art of the good life, of temperance, of moderation, of sofrasine, 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.

15:29All 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 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 had 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. Kind of gives you the sense that Marcus really has talked about.

16:21Just the rhythms of history. Just one generation leading seamlessly into the next, one after another.

16:35Oh, 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. Been together a long time. And I just, I just said, hey, 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.

17:16It'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. 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?

17:48Even 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-dayness 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.

18:13So 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 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. And this is when Seneca realizes that he's old.

18:52that 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 memento more.

19:30There's another stoic concept there, how we never step in the same river twice. But the point is the river is passing us by. Mark Schroes 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. I am 15.64 in. So this is basically the turnaround point.

20:10I'm feeling pretty good. I feel hydrated. The shade has been nice. It's getting hot. I'm way behind schedule. It's 8.40 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 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.

20:39The 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 going to turn around and go back. 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. You raise your threshold higher and higher. until what used to seem like a lot now only seems like a little.

21:21Mark Shrews 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.

21:48I'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. Mark Stavilius, maybe he was riffing on that exact passage. He would talk about this in meditations. He's just like, what are you going to meet the problems of tomorrow with? He says, 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.

22:27And honestly, this is my favorite part. 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.

23:07Now it's just, look 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 of because of what you've just done and you just got to see it through which is where I got to go now.

23:32Well, I did it. 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.

23:50The limit's about... 30 exactly 29 and a half that's where I lost it you know they say um 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 hotter than I thought thus the intersection of it all my son ran the last 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, 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 than what I got in the tank.

24:51And now, uh, now I gotta rest.

24:57Hey, Sam. I'm dying. Yeah. How does this take six and a half hours? Well, that's not a very nice question, is it?

From the publisher

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


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