The Daily Stoic - The Choice Is Clear (But That Doesn’t Mean It’s Easy) | Ryan Holiday Ran The ORIGINAL Marathon

Episode Date: August 15, 2025

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.

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, visitdailystoic.com. 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. Just that you do the right thing, Marks Reelius 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 low, he had to bear. When it comes to doing what's right, the timing is rarely perfect. The bills are always due, the pressures 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. 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. The other day after we dropped our kids off at camp, my wife and I realized we had a little more time for you to be at the office. So we took a nice hike through one of my favorite parks, McKinney Falls here in Austin. And when you live in active life like that, You've got to take care of yourself. You got to make sure you're getting nutrients if you want to go on adventures. And Kachava's whole body meal shakes help you do just that. You mix it up with your favorite alternative milk or water and you're ready to go.

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That's kachava.k-h-a-com code stoic for 15% off. How long have I been a Thrive Market customer? I think literally since they opened. And I invested in Thrive Market a couple of years after that, just got home from a trip. And you know what was sitting in the garage? Our Thrive Market box, because we have it on subscription. And so all the stuff I need to make my kids' school lunches is in there, plus the snacks that I like. It all showed up fast, and I saved up to 25% while restocking.

Thrive has been a lifesaver and a mainstay for our family as a. I said for many years, you can shop by diet, values, even food phases, because, you know, your kids, tastes change weekly. If you've got a busy schedule and you want clean quality options, this is the time. New members to Thrive get 30% off their order and a free gift. You just got to go to thrivemarket.com slash daily stoic to start saving today. And this sale ends on 831. 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 fascinated. I've always loved this exact story. I am doing the original marathon from Marathon to Athens. I just threw up in the Olympic Stadium. That's an experience I didn't expect. Fuck. 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 the way back to 2007 at the earliest when I was reading Robert Greens, the 33 Strategies of War. I remember exactly where I was. I was in a pizza restaurant on Los Angeles and Olympic when I was working in Hollywood. And during my lunch break, I was reading the 33 Schedule of War, and he tells the story about the Battle of Marathon.

One day in early August, 490 BC, 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 new Persia's intentions to capture their city, destroy its young democracy, and restore a former tyrant to the throne, and sell many of the world. the citizens into slavery. 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 forces and soldiers from all over the Persian Empire. Their overmacked. 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 push the Persians back into the marshes at the north end of the plain where thousands drowned. The waters reddened with blood. By nine in the morning, the Athenians had control

of the planes, 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 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 it straggled to a point overlooking the bay of Salarian. 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 sea. Athens was saved.

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 I've always loved this exact story pivotal for me for two years and 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? We went over to his shelf and he told me there was a book by Peter Greene, which I immediately went on Amazon and bought. I start to lead. I have a chapter about this exact passage

and ego is the enemy. This is the breakthrough moment for me. So I'm reading Robert Green'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. It's all you're starting to see how books that shape 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 in my favorite lines in the books. He says, I didn't come here to walk. I came to run. I came to run.

I've got to 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 Stoapokile, where Stoicism was founded, Stoapokile 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. It is 4 p.m. 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 going to be hot in Greece. I'm going to 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. this is beyond that but it's the only slot I have but we just flew in from Texas a couple hours ago and then we have dinner and then I have a talk tomorrow so I'm going to do this run I've done it before it's beautiful it's going to be very hot and tough but you challenge yourself and it all leads you to where you want to go I just hope I don't get heat stroke and I hope I can make it back it is 542 a.m. on June 16th 2025 I just turned 38 this morning, and now I'm going to do a 19-mile training run for this marathon, which is 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 increased. My father-in-law, he's driving me down. I'm going to run along with Santa Ana River, and hopefully I won't embarrass myself. So I've dragged a bunch of people into helping me this morning, and we'll see how it goes. 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. 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 to 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. 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.

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 all right. It should be fun. I think I'm doing all right. 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. We 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. that'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? What mattered was could they put differences aside? Could they push through and do this thing that they desperately needed to do? 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 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 going to 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. 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 Holkin 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 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 noticed in the video, I'm not just wearing Hoka shoes. I've got a Hoka shirt on. I'm running in these shirts.

They had a great running hat. I actually trained in a pack that they had. They carried my water bottle. Carried it all around Greece as we were walking around in our family. Hoka's are lightweight. They're responsive, great colors, easy to keep clean. But the Rocket X3 was awesome. That's what I have on right now.

There's a reason Hocas are in my running rotation. You've probably even seen me interviewing guests on the podcast are 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. It is 530 a.m. And, uh, 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 651 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. There's something catastrophic happens, something catastrophic happens.

No goal, no outcome, just want to finish, just want to do it. 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. You try to get in the right head space. You do your stretching, try to focus, try not to extrapolate. You try to stay present. 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. 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. You know, 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. I know I can do the distance. You know, Epictetus' 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 a little over halfway done as they say halfway is 90% left 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. 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? When I interviewed Courtney DeWalter, one of the great ultramarathons 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 as 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. One of my all-time favorite books about running is Murakami's what I talk about when I talk about running. And he has his 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. Intended to do the last lap around the stadium. They stopped me and have 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. I would have loved to finish so much stronger, but I just ran into a complete wall because about three miles left.

It's like that line from Kipling about every nerve and sinew, except the will that the wheel that says hold on so I gutted it out destroyed my time but not bad I fucking did it I'm here I made it which was the main goal

everything else was extra it was extra 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 pete stroke or sunstroke or even rabdo. I ended up just getting in the hotel pool and just floating there. My entire body exhausted. It took a while to recover. 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've been on a plane all day. I can drive four hours. I hadn't altitude trained. I hadn't adjusted to the altitude and I passed out at the end.

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 going to 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 put 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 enduring. in sports 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 going to courageously explore that?

Are you going to 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 mistakes 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 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 I'm going to 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'm a person who can do hard things I did a hard fucking thing and I take that with me.