Pod Insights The Daily Stoic Premium (🔓) The Choice Is Clear (But That Doesn’t Mean It’s Easy) | Ryan Holiday Ran The ORIGINAL Marathon About this episode When it comes to doing what’s right, the timing is rarely perfect.🎥 Watch the video of Ryan running the ORIGINAL Marathon on The Daily Stoic YouTube Channel: https://www.youtube.com/watch?v=UAdB5ax0r-0📖 Preorder the final book in Ryan Holiday's The Stoic Virtues Series: "Wisdom Takes Work": https://store.dailystoic.com/pages/wisdom-takes-work🎙️ Follow The Daily Stoic Podcast on Instagram: https://www.instagram.com/dailystoicpodcast🎥 Watch top moments from The Daily Stoic Podcast on YouTube: https://www.youtube.com/@dailystoicpodcast✉️ Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemail🏛 Get Stoic inspired books, medallions, and prints to remember these lessons at the Daily Stoic Store: https://store.dailystoic.com/📱 Follow us: Instagram, Twitter, YouTube, TikTok, and FacebookSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. 📢 Share | ⚙️ Manage Subscription
Transcript Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.
0:05 Ryan Holiday? Welcome to the Daily Stoic Podcast, where each day we bring you a Stoic-inspired meditation, designed to help you find strength and insight and wisdom into everyday life. Each one of these episodes is based on the 2,000-year-old philosophy that has guided some of history's greatest men and women, help you learn from them, to follow in their example, and to start your day off with a little dose of courage and discipline and justice and wisdom. For more, visit DailyStoic.com.
0:55 Ryan Holiday? The choice is clear, but that doesn't mean it's easy. He desperately needed the help. He desperately needed the money. Ulysses S. Grant was at rock bottom. Personally, financially, he had just pawned his watch to pay for his children's Christmas presents. He had acres and acres of forest he needed to clear if he was going to claw a living for himself off the land. Yet, in 1859, as I tell the story and write thing right now, Ulysses S. Grant walked into a courthouse to free a slave named William Jones that he and his wife had been given by their father-in-law. Slavery was wrong, and he wanted no part in it.
1:37 Ryan Holiday? "Just that you do the right thing," Marcus Aurelius writes in Meditations, "the rest doesn't matter." But just because they don't matter doesn't mean they're painless. The choice was clear for Grant, but that didn't eliminate the consequences. It didn't lessen the load he had to bear. When it comes to doing what's right, the timing is rarely perfect. The bills are always due. The pressure's always mounting. The sacrifice is always painful. Grant knew this. It's why he didn't wait for a more convenient season to free William Jones. He didn't weigh the pros and cons. He didn't calculate the cost-benefit.
2:21 Ryan Holiday? He simply did what was right because the time to do the right thing is always right now, no matter how inconvenient it may be personally.
2:44 Ryan Holiday? It all comes down to Marathon. Had the soldiers not come in time, had they not made this race, perhaps there would be no such thing as Western civilization. I've always been facetious, always loved this exact story. I am doing the original Marathon, from Marathon to Athens.
3:04 Speaker 01 I just threw up in the Olympic Stadium. That's an experience I didn't expect. Fuck.
3:14 Ryan Holiday? When you're a runner, the question you get the most is, are you training for a Marathon? And for me, the answer has always been, no, not really, or not the way that you think it is. I say, this is the Marathon. Like, life is the Marathon. The day-to-dayness, that's what the discipline is. And that's how I've thought about running, basically, ever since I left organized sports as a kid. I do long distances all the time, but I do it for me. And that was true up until right now, because I am doing the original Marathon, from Marathon to Athens. And doing this has been in my mind for a long time, actually, going all
3:55 Ryan Holiday? the way back to 2007 at the earliest, when I was reading Robert Greene's The Thirty-Three Strategies of War. I remember exactly where I was. I was in a pizza restaurant on Los Angeles in Olympic, when I was working in Hollywood. And during my lunch break, I was reading The Thirty-Three Strategies of War. And he tells the story about the Battle of Marathon. "One day in early August 490 B.C., the citizens of Athens received word that a massive Persian fleet had just landed some 24 miles to the north along the coastal plains of Marathon. A mood of doom quickly spread. Every Athenian..." knew Persia's intentions to capture their city, destroy its young democracy, and restore a former tyrant to the throne and sell many of the citizens into slavery.
4:40 Ryan Holiday? The Athenians head to Marathon, about 10,000 infantrymen. As far as the eye could see, a long strip of land filled with tents and horses and soldiers from all over the Persian Empire. They're overmatched. At the last minute, the Persian fleet disappears and heads back towards Athens, leaving a holding force of 15,000 soldiers on the plains of Marathon. The Athenians begin to panic, except for one commander. What are the Athenians to do? This commander understands that they can't allow this to happen. They can't split their forces. So the Athenians charge, even though they are vastly outnumbered. The Athenians pushed the Persians back into the marshes at the north end of the plain, where thousands drowned. The waters reddened with blood.
5:24 Ryan Holiday? By nine in the morning, the Athenians had control of the plains, having lost fewer than 200 men. The Athenians now had only around seven hours to make the 24 miles back to Athens in time to stop the Persians. There was simply no time to rest. They ran as fast as their feet could take them, loaded down in their heavy armor, impelled by the thought of the imminent dangers facing their families and fellow citizens. By four in the afternoon, the fastest among them had straggled to a point overlooking the bay of Salerion. The Persian fleet sailed into the bay to see thousands of Athenian soldiers caked in dust and blood. The Persians rode at anchor for a few hours and then headed out to see Athens was saved.
6:05 Ryan Holiday? And thus, this is where the word marathon enters, the lexicon enters legend forever. When we think of a marathon as a distance, this is why. I've always been fascinated, always loved this exact story. Pivotal for me for two reasons. Number one, what I remembered is loving this storytelling. And two, because I was working for Robert, I called him and I said, hey, Robert, I'm reading your section on the Battle of Marathon. And I just wanted to know, what did you read? How did that come together? What did you do? He went over to his shelf and he told me there was a book by Peter Greig, which I immediately went on Amazon and bought. I start to read. I have a chapter about this exact passage in Ego is the Enemy. This is the breakthrough moment for me.
6:50 Ryan Holiday? So I'm reading Robert Greene's story. And then I go to the source material and I see for the first time. This is how it works. This is how a researcher and a writer takes a collection of different sources, puts it through their own style, their own lens, and something comes together. I didn't know this was a thing you could run until I read another book. Let me get it. Saw you're starting to see how books that shaped my life. This book here, Murakami's What I Talk About When I Talk About Running. He does this exact marathon. This has been sitting in my mind for at least 15 years. I've been wanting to do this this whole time. One of my favorite lines in the book, he says, I didn't come here to walk.
7:34 Ryan Holiday? I came to run. I gotta think about that when I'm in the middle of it. Even Stoicism itself as a philosophy is rooted in the battle of Marathon. Not just because it saved Greek civilization, but the sto apo kilo, where Stoicism was founded. Sto apo kilo means the painted porch. It's not the porch itself that was painted. It's a series of famous paintings hung above that porch. And one of those paintings depicts the victory at Marathon. And its main architect is shown there at the front, exhorting his men.
8:14 Ryan Holiday? It is 4:00 PM in Palm Springs. It is 105 degrees outside. My wife says I have a mental illness, but I am training for this marathon. It's gonna be hot in Greece. I'm gonna do it early in the morning. But the idea is you do it when you don't want to do it. You push yourself when it's hard. You try to keep it within reason or bounds. Maybe this is beyond that, but it's the only slot I have. But we just flew in from Texas a couple of hours ago. And then we have dinner and then I have a talk tomorrow. So I'm gonna do this run. I've done it before. It's beautiful. It's gonna be very hot and tough. But you challenge yourself and it all leads you to where you wanna go. I just hope I don't get heat stroke and I hope I can make it back.
8:57 Ryan Holiday? It is 5:42 a.m. on June 16th, 2025. I just turned 38 this morning, and now I am going to do a 19-mile training run for this marathon, which will be the furthest I've done so far. That's the idea, it keeps you young. I'm pushing myself, I'm up early before it gets too hot, like I'll have to be in Greece. My father-in-law, he's driving me down, I'm gonna run along the Santa Ana River, and hopefully I won't embarrass myself, because I've dragged a bunch of people into helping me this morning, and we'll see how it goes.
9:34 Ryan Holiday? So it's roughly one month to the marathon, and I am doing a very steep uphill run in Utah, and I've just been warned that there is a very protective moose and two babies on the trail I have to look out for. So, you know, danger is everywhere, I guess. I thought I was going for a peaceful run, and now I'm on the lookout for this, but I thought training on the incline would be good training for the marathon. The idea is you do hard stuff. The whole point of Stoicism, Epictetus said, was to be able to say, when you meet a challenge, this is what I trained for, and so this is what I'm training for. I just happened to get to do it in front of a very lovely waterfall.
10:20 Ryan Holiday? And then we flew to Greece. I trained at the Acropolis, I trained in Ithaca, I trained running up Mount Olympus, I went on hikes with my family, I swam in the Aegean. Zeno, one of the founders of Stoicism, would say that well-being is realized by small steps, but it's no small thing. I think the same is true for conditioning. We build up our endurance, we build up our muscles, step by step, mile by mile, session by session. So I just made it here up to the top of the hill across from the Acropolis. Trying to do some hill training. The marathon is in less than three weeks.
11:05 Ryan Holiday? I've been doing some good runs. It's been hard to get the speed that I need to train on this thing, but it's going alright. Should be fun. I think I'm doing alright. It's crazy. You can sort of see out here the ocean there. We toured the Acropolis yesterday. I got to see what the Persians did when they destroyed it the first time. Got to see what the stakes of this whole thing were. Saw statues to some of the major figures. This is gonna be cool. It's gonna be the first run that I've ever done. It's got this whole history attached to it. This whole storyline attached to it. And you realize, yeah, this wasn't just a 26 mile odd distance. This was an existential fight, right? The whole of Greece hung in the balance. What mattered was could they come together?
11:48 Ryan Holiday? What mattered was could they put differences aside? Could they push through and do this thing that they desperately needed to do?
11:57 Ryan Holiday? Well, tomorrow is the big day. Today was my last day of training or last day of running. I would have liked to go for a long run, which is helps me sort of regulate and get my head right. But I was thinking about this thing that Kate Courtney, one of the great mountain bike racers of all time. She's an actual Olympic athlete. She said that one of the things she thinks about from her coach all the time is do you want to be fast now or fast later? Be wonderful to bust out a nice run today, but that would affect performance tomorrow. So I'm gonna do 2.25. And now I am going to do a little swim just to get in that cardio space, but not put so much wear and tear on the body.
12:36 Ryan Holiday? So when I was starting to train for this thing, I read this article about these carbon fiber shoes, which is what marathoners are using these days to post these crazy times. I emailed the people I know at Hook and I asked, you guys make a carbon fiber shoe? And they said, actually, yeah, we just came out with this shoe called the Rocket X3, which has a carbon fiber plate on the bottom and it's got this extra cushion in it. And so it sort of bounces off the pavement. It makes you go much faster and take some of the load off of it. I really liked them. I did a lot of my training in the shoe. They were great. You've noticed in the video, I'm not just wearing hooker shoes. I've got a Hoka shirt on. I've been running in these shirts. They had a great running hat. I actually trained in a pack that they had. They carry my water bottle, carried it all around Greece as we were walking around in our family. Hokas are lightweight, they're responsive, great colors, easy to keep clean.
13:20 Ryan Holiday? But the Rocket X3 was awesome. That's what I have on right now. There's a reason Hokas are in my running rotation. You've probably even seen me interviewing guests on the podcast or walking around the bookstore and check them all out at hoka.com. We drove the course a few days before. That's when the reality of it sets in. It's a long way by car and then you're going to have to do all this on foot, powered by foot. And you've got only a few hours to do it.
13:55 Speaker 02 It is 5:30 a.m. and I'm with my crew and driver in the tiniest car that you've ever seen. And we're on our way. We're here at the start of the original marathon. It is 6:51 on Sunday, July 13th. And I'm about to do it. It's 26 miles. Weather is amazing and I'm feeling good. I'm not nervous. I'm a little nervous that I'm not nervous, but I think that's the result of the training. I'm in a good spot. I'll tough it out regardless unless something catastrophic happens. If something catastrophic happens, something catastrophic happens. No goal, no outcome, just want to finish, just want to do it.
14:38 Speaker 02 And I want to experience it. So I'm going to try to be present for the whole thing and enjoy it because that's what it's about.
14:49 Ryan Holiday? You try to get in the right headspace. You do your stretching, try to focus, try not to extrapolate, try to stay present.
15:02 Ryan Holiday? So I will disagree with one little part in what I talk about, when I talk about running. He says, "As those who have watched the TV broadcast of the marathon at the Athens Olympics, after the runners leave marathon, at one point, they go off to the side of the road and run past some less than distinguished ruins, and then they return to the main road." I would not say that these are less than distinguished ruins. I would say these are some of the most impressive and meaningful ruins in the entire world. And I was struck by them.
15:30 Speaker 02 Right behind me, this giant mound on the other side of this grass are the 192 Athenians who died at Marathon, to whom we owe basically all of Western civilization, as we do to the 300 Spartans. Theirs was not to reason why theirs was, but to do and die. Or as the Spartan monument says, "Tell a stranger passing by, here obedient to their laws, we lie." That's what I'm thinking about, three and a half miles in.
15:58 Ryan Holiday? I know I can do the distance. You know, Epictetus's thing is that you should only enter competitions where winning is up to you. My thing is, as long as I don't quit, I'll probably make it to the other side. That's one of the other things that the Stoics talk about, that you undergo a hard winter's training, you practice physical discipline or challenges, so that when life throws you physical, spiritual, mental challenges, you have an experience on which you can draw, that you know that you're someone that doesn't quit, that you're someone who can get through things, you understand how you have that feeling of limitations, or that you're at your limits, but that you can push past it. I'll be better for the training that I've already done. I'll be better for putting myself out there, trying something that's a bit beyond my grasp, maybe.
16:47 Speaker 02 A little over halfway done. As they say, halfway is 90% left.
16:54 Speaker 01 And there's a, there's a blue trail, a blue line. All I'm thinking about is Joni Mitchell's line about being prisoner of the white line of the freeway. 14 miles, 12 to go.
17:09 Speaker 03 Whenever it gets to the hardest part, is there going to be a specific bit of advice that's going to go through your head?
17:14 Ryan Holiday? When I interviewed Courtney DeWalter, one of the great ultra marathoners of all time, she said, when she starts to come up against those limitations, or she starts to feel it, she says that makes her excited. She calls it the pain cave. And instead of stopping and going, oh, this is painful, oh, this hurts. It's about exploring how far back that cave goes, what's inside it. You know, the stuff's talking about everything has two handles. You can see something that's hard and painful, and that's why you shouldn't do it. Or you can think of something as hard and painful, and that's why you should do it. And you should learn from it and open yourself up to it. And so I can imagine, and I know I've drawn on that in different sort of challenges I've done in my life before, it's like, yeah, let's see what's in there. Let me see what I'm capable of.
17:59 Ryan Holiday? One of my all time favorite books about running is Murakami's What I Talk About When I Talk About Running. And he has this passage, for him, running is both an exercise and a metaphor. He thinks this is why so many writers like to run. He says, running day after day, piling up the races, bit by bit, I raise the bar. And by clearing each level, I elevate myself. At least that's why I've put in the effort day after day to raise my own level. I'm no great runner by any means. I'm at an ordinary or perhaps like a mediocre level, but that's not the point. The point is whether or not I improved over yesterday. In long distance running, the only opponent you have to beat is yourself, the way you used to be.
18:44 Ryan Holiday? I intended to do the last lap around the stadium. They stopped me and had me put my shirt back on, which I probably shouldn't have taken off. And if anything, it contributed to the sunstroke that I think I obviously had.
18:59 Speaker 01 I would have liked to finish so much stronger, but I just ran into a complete wall. There's about three miles left.
19:09 Speaker 01 Like that line from Kipling about every nerve ensign you except the will that
19:18 Speaker 01 the will that says, hold on. So I gutted it out.
19:23 Speaker 01 Destroyed my time. But not bad. I fucking did it. I'm here.
19:29 Speaker 01 I made it.
19:31 Speaker 01 Which was the main goal. Everything else was extra.
19:43 Ryan Holiday? It was a long drive back from Athens and I was just so out of it. I could barely remember the name of my driver and cameraman. When I got to the hotel, I threw up several more times. It would be a few hours before I could hold anything down, even water. I started to worry that I had heat stroke or sunstroke or even rabdo. I ended up just getting in the hotel pool and just floating there. My entire body exhausted. Took a while to recover.
20:12 Speaker 02 Okay, so I did it. What did I learn now that I am somewhat back in command of my faculties? Preparation is everything. I did lots of training. I could have handled the nutrition side of things better. I could have started a little bit earlier. It's not all about discipline. I mean, obviously, discipline is incredibly important. But without the virtue of wisdom, which is understanding the right place to apply that discipline and how to support that discipline, you can get yourself in some very rough spots. When I did my run up to Cerro Gordo, which is one of the other hardest physical feats I've ever done, it was the same thing. I'd been on a plane all day. I could drive four hours. I hadn't altitude trained. I hadn't adjusted to the altitude and I passed out at the end.
20:57 Speaker 02 I woke up several hours later and it was good, just like I am now. And so, discipline is something we have to moderate with. Wisdom. What is the best nutrition? What is the best plan? How do you stay out of the sun? How do you take care of your body? I thought my feet were gonna be in horrendous shape, but I think I did a good job training up until the race. I got the blisters not from running, but from all the walking through all the historical sites in Greece and carrying my kids and whatever. I handled that well, so I didn't have any foot issues. So I handled that one. But then I, you know, I just got my ass kicked by some other things. Seneca talks about how he pities the people who haven't been through adversity or difficulties because they don't know what they're capable of. And that's one of the things we learn when we do endurance sports,
21:42 Speaker 02 when we do feats of strength or whatever, is you get a better sense of what you are capable of, where your limits are, where your pain cave is. Are you gonna courageously explore that? Are you gonna turn tail and head the other direction? I think the thing I was struck most by as I did the race is just all the people that have come before me that have traveled that very distance and the stakes that were there when they did it. I was lucky enough to get to follow in those footsteps. I was lucky enough to spend a couple of hours by myself in my head. In what I talk about when I talk about running, it talks about how you run to acquire the void, to get to the place of nothingness and stillness. And I had that. I had several hours of stillness and peace totally to myself. And it was wonderful.
22:27 Speaker 02 I'm gonna bring that home with me. I'm proud of myself. I have a sense of what I'm capable of, what I can do, and that I'm not a quitter, that I push myself and I do hard things. Like, what I took from this is that I am a person who can do hard things. I did a hard fucking thing and I take that with me.
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