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Running 50 Kilometers Through Rome To Understand Stoicism

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The narrator embarks on an ambitious 50-kilometer run through Rome to physically embody the core tenets of Stoic philosophy, specifically the practice of doing hard things for their own sake rather than for external validation. Starting from his Airbnb accommodation in the city center and finishing where he began after covering 31 miles, the journey serves as a moving meditation on building an "inner citadel." As he passes significant historical sites like Hadrian's Tomb, which houses the remains of Marcus Aurelius, he reflects on how physical endurance reinforces mental resilience. The run illustrates that true strength comes from within, acting as a fortress against external chaos, much like the inner reservoir of fortitude attributed to George Washington by Thomas Paine. Throughout the course, the runner visits landmarks that highlight the Stoic rejection of vanity and mob mentality in favor of self-mastery and virtue. He stands before Marcus Aurelius's victory column, noting that the emperor died before seeing it completed, underscoring that trophies are not for us but that the benefit is inherent in the act of overcoming difficulty. The journey continues along the ancient Appian Way, where he contemplates the passage of time and mortality, inspired by Seneca's reflections on aging trees and the relentless flow of history. Even when facing setbacks like getting lost or running behind schedule, the narrator applies Stoic principles to accept the unexpected with grace, viewing obstacles not as stoppages but as opportunities to test one's preparedness and adaptability. The final stretch of the run reveals that the greatest challenges often occur in the last portion of any endeavor, a concept the narrator compares to the difficulty of finishing a book or project after the initial hard work is done. Drawing on Epictetus's advice to rely on internal resources rather than external circumstances, he pushes through fatigue and heat, realizing that the true measure of character is found when one keeps going past their perceived limits. The experience culminates in a profound sense of accomplishment not because of crossing a finish line for glory, but because he has proven his capability to endure hardship. Ultimately, the run reinforces the idea that life's best rewards lie on the other side of moral courage and the willingness to take risks, a lesson that directly influenced his own career transition from corporate work to writing.
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I'm going to run the furthest I've ever run in my life. I'm going to run 50 km through the streets of Rome, the eternal city. And 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 50 K? Because it's hard. That's the whole point. The Stoics said that doing hard things was good for you. Along the run, I'm going to stop at a dozen or so places that are not just significant in terms of the history of Stoic philosophy, but illustrative of this idea of why we do hard things, what those hard things can [music] teach us. I'm starting at this place we booked on Airbnb here in the center of Rome, and I'm going to be finishing there roughly 50 km or 31 miles later. So now it's just a question, and this is ultimately what Stoicism is is, am I going to do it? >> [music] [music] >> 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 the thing you retreat to, the thing that protects you. And and and when we do hard things, [music] when we train, when we push ourselves physically, that's what we're doing. We're we're reinforcing, we are building that inner citadel. And that that inner citadel is what you draw on, that inner reservoir of strength, [music] what Thomas Paine said of George Washington that it it was this cabinet of fortitude. That's what protects us from the things that are happening outside. That 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. Look, do do we do hard things cuz we want to impress people? Or do we do hard things cuz we want to beat other people? Do we do hard things cuz we want trophies? No, that is not why. Behind me is one of the great trophies of history. It's Marcus Aurelius' victory [music] column. It's what they put up in honor of his victories in the Marcomannic War. It's 400 ft of carvings. It stretches almost 200 ft in the air. It's uh it's 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. [music] And then in the 15th century, a pope knocked him off and put St. Paul up on top. And they they put a new 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. [music] I I doing challenges where the victory is what I get out of it. >> [music] >> 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." 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 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. Uh especially when you were the most powerful person in the world. I I love I 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 uh 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 who had good reason not to like Marcus 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 uh I still have the furthest that I've ever run to go. There's a Stoic named Agrippinus who was banished from Rome by the emperor for running afoul of him. He was banished by Nero. And uh when he's told he's he's going to he's going to have to leave, he just says, "Okay, we'll have our 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? You got to be prepared for things to go wrong, and they they just did. I just got lost. I did a 1-mi 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, "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. I just got to go down here, go here, and uh we'll be good to go. >> [music] >> So, one thing we know about the Stoics is that they hated the Colosseum. They hated the violence. They hated the the mob mentality of it. They hated the brutality, the the mindlessness of it. Seneca talks about how degrading and gory and disgusting what happened in the floor of the Colosseum was. Marcus Aurelius supposedly would read his philosophy or write in Meditations in his 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." In another passage of Meditations, he talks about being like those gladiators who were torn apart, bloody, begging to come back the next day. He He didn't actually mean that as a positive. He He meant like they needed to change. There There were that that life was telling them something. It was It was beating them up. It was destroying them, and and they weren't going in the right direction. The The point is, I think they would have liked Theodore Roosevelt's idea of 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. 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 And one of the most powerful images in the Stoic virtues comes from here, from Circus Maximus. The idea of sophrosyne that the chariot racer, 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. And so the The image of the charioteer was emblematic for the Stoics of the The art of the good life, of temperance, of moderation, of sophrosyne, which, you know, any kind of challenge requires of you. 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 your marks, your benchmarks, which are all of which I'm thinking about right now. And now I get to run a little bit on the actual track, cuz you can come down and do it, which is pretty incredible. >> [music] >> All right. Now the pavers on the uh 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 jeeps and tanks when they retook Italy town by town. And then uh you know, here we go. We get to run along them ourselves. It's still here. Kind of gives you the sense >> [music] >> that Marcus Aurelius talked about, just the 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. We pulled over on the side. I hadn't planned it. We were just hanging [music] out. We've 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 it it are you seeing this go the same direction I'm I am?" >> [music] >> And uh 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 [music] 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 [music] 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 [music] 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. [music] 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?" Even when it's not totally what you imagine. Right? There's the doing the hard things. There's the 20 seconds of of insane bravery and commitment, the leap. Then there's also the day-to-dayness of it. And I do [music] 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 this is supposedly this is Seneca's tomb. We don't know for certain. It's got no inscriptions and uh it's here on the Appian Way. I am almost 13 mi 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's he talks about how he comes back to the house that he grew up at. And uh the trees are starting to die around it and he wants to criticize the caretaker for not taking care of them. And the the caretaker says, "What are you talking about? These trees were planted when you're born. [music] They're dying cuz they're old." And this is when Seneca realizes that he's old. That we can see sometimes in nature the passing of time that is uh invisible to us because we see ourselves in the in the mirror each day. Uh 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 but you look at it and you go, "Oh, there's more gray hairs. There's more wrinkles. You could see the 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 [music] been is a really good reminder of that momentum. Or 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. And then Marcus Aurelius talks about time being this vicious unrelenting ceaseless almost merciless flow of events faster and faster and faster and it's taking [music] 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. >> [music] >> I am 15.64 in. So, this is basically the turnaround point. [music] 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 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 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 To 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, uh almost 16 miles in, taking a little bit of a pause, and then uh I'm going to turn around and go back. >> [music] [music] >> You know you're doing something crazy when when you think only 7 miles left. But, that's where I am. 7 miles left. But, that's kind of the the good thing when you train you push yourself you raise your threshold higher and higher until what 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 the reins of the horse in the opposite hands, getting practice doing it the hard way, doing hard things, so then when you uh are in the middle of a hard thing, things that you used to think were too hard, you actually look forward to. I've officially done a marathon. So, I have 5 ish or so miles left. My final thought as I get through the home stretch is this idea from Epictetus. He says um you know, whatever difficulties you face, understand what resources you have inside you. Marcus Aurelius, maybe he was riffing on that exact passage. He would talk about this in Meditations. He says like, "What are you going to beat 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 6 miles? I mean, the same willpower and strength and training that I got through the first 26 miles. And And honestly, this might This is my favorite part. First off, cuz you know, they say it's not really pushing yourself until you get to your limits. It's really >> [music] >> 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 2/3 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 you're operating under some momentum. You've crossed most of the difficulties off. Now, it's just Like, some some people say, you know, the last 10% >> [music] >> takes 40% out of you. And that's true, but I also think you're in a rhythm. You you have this sense of what you're capable of cuz of what you've just done. And uh you just got to see it through, which is where I got to go now. Well, I did it. Just barely. I was dying at the end. That was a limp across the finish line, I'll tell you what. The limit is about 29 ooh. The limit's about 30 exactly. 29 and a 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. [music] 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 [music] best. The fact 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 and what I got in the tank. And now uh now I got to rest. Hey Sam. >> Mhm. >> I'm dying. >> Yeah. How did this take 6 and 1/2 hours? >> Well, that's not a very nice question, is it? So we started this apartment we uh booked on Airbnb this morning and here we are 31 miles back where we started. It's actually pretty incredible. Look at this um This building was built 2,000 years ago. >> These are all tombstones. It's kind of a memento mori. >> Historians would say just like the people on the uh on the Appian Way every single one of these monuments is for someone who thought they had more time put things off who maybe left something on the table. Anyway, that's what I'm that's what I've been thinking as I I through this every day. But it's really been an incredible place to stay. And it's funny because I actually started my writing career. First house my wife and I bought. We would host it on Airbnb when we would travel. And it kind of is what helped me transition from being a corporate person to a writer. As we bought this house and then listed while we were gone and then I'd work there during the week and we'd rent it out on the weekends. That was like how we paid for it and that's what helped me take the risk, the jump to do The Obstacle Is the Way. And my publisher was not super excited about a book about an obscure school of ancient philosophy, but I thought life's too short. They're going to pay me something, so I might as well do it. I'll figure out a way to make it work financially. And I did and all this, everything that's happened since is on the other side of taking that that risk.