The Daily Stoic - BONUS: The Advice Ryan Got Before Running His First 50K

Episode Date: September 14, 2026

Ryan knew running 50 kilometers through Rome would require more than just being in shape. So he turned to Luke Tuttle from the blog Ultra Running Destinations for firsthand advice on how to prepare for everything the run might throw at him.🎥 Watch Ryan run the Stoic 50k here: https://www.youtube.com/watch?v=R2LNSVXbsaI👉 Read Luke Tuttle's article about his 53k ultra run through Rome: https://www.ultrarunningdestinations.com/home/53k-along-ancient-roman-roads-and-trail-rome-italy🎟️ DAILY STOIC LIVE | Ryan Holiday is coming to a city near you! Grab tickets here |  https://www.dailystoiclive.com/🎙️ AD-FREE | Support the podcast and go deeper into Stoicism by subscribing to The Daily Stoic Premium - unlock ad-free listening, early access, and bonus content: https://dailystoic.supercast.com/✉️ FREE STOIC WISDOM | Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemail--Stop online threats before they become real-world attacks. Visit ironwall.com/DAILYSTOIC and request a free Risk Assessment to see exactly how exposed your executives are.--Wealthfront’s high-yield cash account: https://www.wealthfront.com/stoicThis experience may not be representative of other Wealthfront clients, and there is no guarantee of future performance or success. Experiences will vary. Ryan Holiday, who’s a client of Wealthfront, receives cash compensation from Wealthfront Brokerage for paid testimonials in his podcast, creating a conflict of interest. More details available via the referral link. The Direct Deposit Plus Investing Program from Wealthfront Advisers LLC and Wealthfront Brokerage LLC provides eligible clients a 0.25% APY increase above the base APY on eligible Cash Account balances (up to an overall boosted rate of 4.30% for a limited time when including the three month 0.75% APY boost for new clients) when you direct deposit $1,000 a month, plus open, fund, and maintain an investing account. Wealthfront may change or end the program at any time and determine eligibility at its discretion. Terms apply. Full details at wealthfront.com/promo-terms.The Cash Account, which is not a deposit account, is offered by Wealthfront Brokerage LLC ("Wealthfront Brokerage"), Member FINRA/SIPC. Wealthfront Brokerage is not a bank. The Annual Percentage Yield ("APY") on cash deposits as of January 30, 2026, is representative, requires no minimum, and may change at any time. References to the APY for the Wealthfront Cash Account, including any APY increase, are to the APY paid by insured depository institutions that participate in our cash sweep program (the "Program Banks”). Wealthfront Brokerage does not pay interest. Wealthfront Brokerage sweeps cash balances to Program Banks, where they earn the variable APY.Instant and same-day withdrawals use the Real-Time Payments (RTP) network or FedNow service. Transfers may be limited by your receiving institution, daily caps, or participating entities. New Cash Account deposits have a 2–4 day hold before transfer. Wealthfront does not charge fees for these services, but receiving institutions may impose an RTP or FedNow Fee. Processing times may vary.. Fees & Eligibility requirements may apply to certain checking features.Investment advisory services are provided by Wealthfront Advisers LLC, an SEC-registered investment adviser. Investing involves risk, including the possible loss of principal. Securities investments are not bank deposits, bank-guaranteed or FDIC-insured, and may lose value.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Welcome to the Daily Stoic podcast, designed to help bring those four key stoic virtues, courage, discipline, justice, and wisdom into the real world. So my dream vacation is lots of time with family, lots of running or swimming. Like I'm pushing myself physically and then just spending a lot of time hanging out with the people I like the most. So we had this trip to Rome planned for this summer. Last summer we were in Greece and I ran the original. Greek marathon by myself. I ran from a marathon to Athens. And I wanted to do something like that

this summer, but I didn't want to do the same thing again, so I didn't want to do just a marathon. So I had this idea of doing an ultra marathon, 50 kilometers through some of the stoic sites in Rome, which we ended up doing. It was incredible. We have a whole video about it. I'll link to that in today's show notes. Airbnb was nice enough to sponsor it. We stayed in this amazing palazzo that we We booked on Airbnb. It was really cool. All that's in the video. But as I was training for this, I didn't want to die.

I didn't want to get heat stroke again. I wanted to know what I didn't know. So I was looking, had anyone ever done a 50K Ultra through Rome? And I was Googling around about it. And we came on this website called Ultra running destinations. It's this blog run by this guy named Luke Tuttle. And basically, he had like a job in banking or consulting or something in Europe. And so he was always in these different European capital.

or he'd take weekend trips and he'd try to land at the airport and then run into the city and do these sort of long destination ultramarathons along the way. It was totally crazy. It's the only one I'd found that done anything like this. So I going to something the Stokes talk about and I talk about is like, when you're going to do something, go learn from someone who has done something similar. So I reached out to Luke. I had a million questions for him. And the conversation was so great. Actually, we turned it into a mini podcast. So I'm going to bring that to you as a little bonus episode here.

And we talked about a bunch of interesting stoic themes and just the idea of doing hard things in this episode. You can check out his stuff if this is at all attractive to you. If you're a crazy person, you just go to ultra running destinations.com to check out of stuff. I'll link to his one about doing it in Rome. But let's listen to this combo. And why don't you go check out the... stoic 50K video on the Daily Stoic YouTube channel, which I will link to. And yeah, thanks to Airbnb for sponsoring. And I like the idea. Maybe I'll do an ultra marathon every time I fly somewhere to do a

talk. Just show up to the talk all covered in sweat and stuff like like Luke would show up in the hotel lobbies. That sounds like a good idea. No, I will not be doing that, but I do like to run in the cities that I go to and I am on tour right now. You can grab tickets at dailystokelive.com. to see me in Nashville, in Boston, in Philly, in D.C. And then the whole month of October, I'm going to be in Australia doing a bunch of dates as well as New Zealand, all that at dailysooklive.com. Tell me about what makes a person get off a flight and then just run 53 kilometers into a city.

Whatever possess you to do this? The crazy thing is I did that every three weeks for at least three years. What? I had the opportunity to work in Europe for a bank in Stockholm. I was in Stockholm quite a bit, Berlin quite a bit, for these kind of two-week stints. And I worked quite a lot. And it was like, well, it's a great counterbalance to that

was to go do a journey of my own on the weekends. And I kind of have this goal to visit every European country and ended up mostly doing that. So you would fly into a city, not have any stuff with you, really, and you would just run from the airport into the city? Yeah, there was a variety of modes, but that was largely it. Or meet someone on the internet would pick me up.

I had somebody in Bulgaria, a couple folks that planned trips for people, and I found them online and said, hey, come into Bulgaria, would you help me playing around? They're like, sure. And they picked me up to the airport, and then they drove me into the wilderness, and then said, we'll see you in two days.

What was the longest you did? So my longest run like that was about 80K. They're generally always 50K, so 30 miles. So one time I misplanned and it was like 45 miles, something like that. But I didn't like to overplan. Like there's an art to knowing how to get in and get out. He's know how to get there. But not planning it in such detail. There's no like exploration or surprise or realizing that the map is wrong. Like this is old. This is now private land. And they're like, I can't run.

through here. What do I do? So that made it fun. What did you do for gear? Like, you didn't have a suitcase or, like, how do you just run from the airport? That was the craziest thing reading about what you did. So I had a camelback backpack. It's meant for, I think they market it, they call it the mule. It's marketed for mountain biking. And it perfectly fit two of these compression sacks. So I could get the clothes I needed for the weekend. So I had a pair of like Marino wool pants, a marino wool shirt, marino wool underwear. So I had, had clothes I could wear when I wasn't running. Yeah.

And then I would have my running clothes, which would be, you know, a pair of like windbreaker pants, my shorts, my shirt, a long-sleeged shirt. And then I'd have an extra, you know, dry shirt. And that was kind of it for the weekend. Rome is obviously the one I'm most interested in. I'm doing a 50K in Rome in about 10 days. I was looking like, has anyone ever done this? What course should I do? And this is how I found your stuff?

What do you feel like what surprised you about doing it? What did you learn? What were your favorite things to see? Yeah, the best part of the trip is, and with so many of these trips, is you can read about history. Think you understand it. But then when you're on a path, like a pilgrimage path, and you can see in the limestone the ruts from the carts, the ox carts, right?

Yeah. It completely changes your own. understanding of what it is you're traversing, right? And then the history that occurred there, and then you think about a thousand years, I don't know, hundreds of years of people that traverse those steps before you. It's almost surprising it's real. Like you see the map. You see people have run it. But then when you're on it, it gives you this greater appreciation for our role in the world or our space in the world that you're one blip on this long journey that many other folks have made.

It's still the same road. It goes to the same place. These other people saw this with their eyes. And it's largely unchanged since I think it was built. So I guess maybe that's surprises. It's how enduring it is. The Appian Way is mind-blowing to consider one that, I mean, it's still a road, still paved with the same stones,

and how many thousands and thousands of years people have been traversing it. Up until, you know, the allies came down it in their tanks, you know, to liberate Italy, the generations upon generations and the different forms of technology. And yet, as you're running alongside it or walking down it, just how many people have done that exact same thing as you? A lot of time to reflect on the trip, walking on the course. You also go through catacombs. Yeah. So, I mean. It's lined with tombs, right?

It's lined with tombs from some of the most famous Romans who ever lived, who we don't even remember. That's exactly right. And now they're just some crumbling stone in an interesting statue on the side of a path that's now a running trail for some people. I imagine if you're doing it multiple times in multiple cities, you're pretty comfortable with that distance. But how did you handle Rome specifically?

Did you hit a wall at some point? Would you remember about that run? For whatever reason, one of the most memorable parts was getting to the, the airport. So I flew in on, I think, Ryanair, so it goes onto another smaller airport outside the city. The fueling for the run was some coffee. I think I had a couple of cap pinos and some croissants, probably put a bunch of Nutella in there. And gummy bears? You like gummy bears, right? I love gummy bears, because gummy bears and twicks, you can get anywhere. I have yet to find a place on the globe where you can't get gummy bears and twigs. So that's my, what's in my pack. But

I love the European copy. I love things like croissants. So, So it was a very simple start. I'm just this inauspicious waiting area at an airport. I'm having some coffee. I'm off the plane contemplating. Now I need to call up a cab to take me outside the city. But the very start of the run was super interesting because the entrance to the path itself was a fairly ornate stone gate

that was in quite some disrepair. And as I looked at it, I'm thinking like, am I even in the right place? Is this something that others would do or contemplate? For the very beginning of the run, I mean, that was a lot of the run was these, it really ruins. They're more recent than the Roman era,

but these ruins are folks that had estates with, again, grand entrances, and now it's, it seemed that it hadn't been populated in very long time. But yeah, a very, kind of inauspicious start of a relaxing morning want some coffee and compliment like, I'm going to be out for the next nine to 12 hours.

I don't know what the weather is going to be like. It ended up raining quite heavily towards the end of the run that I did. But that's how most of the runs I've done are as time spent, enjoying the star and not really thinking about the finish is kind of enjoying it. Well, that is the difference between doing it as part of a race and then doing it as part of a kind of a solo test, right? It is like the race is the competition, you're doing it with other people, you're checking your pace. But there is something about just a sort of a solo cut and you're like, hey, am I capable of doing it?

So it's just a test with yourself. And then I think secondarily, the experience was the point of it. So if you zone out or you disconnect, that's the only way you lose. It's really, can you soak it in and experience it as it's happening? Exactly. And that's why I'd say on these runs, I don't. And it's a good question. I hit the wall.

I don't run the whole time. I take the time to sit down and have my lunch and gaze out into the countryside or walk for a period. That part of that run went through a small town. I walked through the town. I just took it in. There's no rush to the end. The point was to look at the details along each step of the way. And there were some parts on the run, particularly in the first quarter of that run.

where you're on a single track mountain trail, and all of a sudden there'd be a section with the paved stones. Yes. And then as I just stand there and be like, I mean, where did the other stones go? Where did this path go? And there's no reason to like rush through it because it's just me. But so you'd really look at those details,

something that you kind of rarely do. Because I'm by myself. There's nothing else I need to be to. I can check in any time at the hotel. So it's, yeah, it's very different than a race where I feel like in a race, there's an ego element of like, well, I want to finish at least midway or at least feel proud about my time, whereas on these runs, it was much more about what would I remember later? And you're probably the only person I've ever told about being in the middle of single track trail and seeing a path. And I've always wondered, like, what was that path there for? That's really good advice.

So I want to, I'll take some time to contemplate and actually take in what I'm seeing. I wanted to ask you about the stones, though, because that, I always think when I'm sort of, if I'm going to try something or I'm going somewhere I've never been, you know, you want to get all the positive advice. That's great. But I also try to go like, this is, I think, kind of a stoic exercise is like, what could go wrong, right? What do I need to know about?

Like, what are the things to be worried about? And I have talked to some people that have done some long runs in Rome, including the Rome Marathon. And they said that the cobblestones and those sort of paving stones, it, it's, it's, you know, It sneaks up on you the toll it takes. And I just wondered what that experience was for you doing that level of distance. Was it significant or is that not something to worry about? It's something I worry about my daily running and because of that, I mostly run in the grass. What I seek out is irregular terrain.

So when I do my regular training, I'm literally running through people's yards or if it's a paid path, I run on beside the path. particular on that run, the, there are points where the, the road are extremely, extremely irregular. So it was much more comfortable to run the grass.

But a lot of that main path there, it is kind of park grass-like area. And I spend most of my time running through that. And I find that just as keeps your body out of the same groove. Because kind of not the thought is if you're just running on the road, your body goes through the exact same motions over and over. and that's my personal thing. That's what leads to the injuries,

and I've been unfortunate not to be injured, and I think part of that is running through the grass or in the dirt along the path or the gravel. The irregularity is kind of the point, I guess, is what you're saying. It's like you run on a treadmill, you're living, you might as well be running, you know, in space or something. It's not real. And then when you're running on the road,

you can kind of become soft or dependent on the terrain conditions being favorable and that's that's not reality that's certainly not reality when you're running in a place many centuries old exactly and it forces you to be in the moment like you you have to look at your feet i had a friend actually asked me one time he's like what do you look at he's like i feel like i have to look at my feet the whole time when i'm running on the trail and thought i mean yeah yeah there might be a hole or something else that you need to to think about so so it definitely we're seeing me in the moment much more than the road running where you can kind of just turn it off. Yeah. And I think for me, because I'm going to be starting in the city and kind of running out and

around and out the city and then back in, I do think there'll probably be more of the cobblestones than on your way in, which it sounds like you kind of started in the rural area and major way towards, I don't want to say civilization, but towards the city itself. So that is one of my things I'm worried that like, yeah, my legs will just be exhausted in a way that I didn't anticipate because there's not a lot of cobblestones to train on here in Austin, Texas, believe it or not. You'll be walking and running anyhow, right? So you'll be taking out. What's the top site that you're looking forward to soon? I'm going to try to do most of the Stoic sites. Like one of my favorite runs I ever did was in Rome. You know, you're out for running. I got to Circus Maximus and it was open and no one was there. And I just found myself running laps around. you know, this great chariot track that people have been racing on for for centuries. That was special. And then my wife and I did most a big chunk of the Appian way on bikes,

you know, 15 years ago. And so that's the part I'm looking forward to most. I'm going to go up and then kind of turn around at Seneca's tomb. That's part of it. So I have a I have a handful of sites that I want to do. I've seen them all before. So it's going to be more kind of passing acknowledgement of them than like seeing it for the first time. But I've got a bunch of boxes I want to check for sure. Very cool. Planning on any other of the main tourist site there in the city? Yeah, we're going to, we're going to do the whole thing. We're going to be there for like 10 days or so. I'm bringing my kids, but this is this is my one little me time in the trip. So I'll wake up early and, you know, probably be getting back just as they're gearing up for the day,

hopefully. So that's kind of that. I did. I did a similar thing in Greece this summer. I was going to ask you, did you do one of these in Greece? So in Greece, I did the marathon, the authentic marathon. Yes, I did that too. So that was super cool, particularly the start. I hiked around the city. I didn't do a large run afterwards.

So you started in marathon and went to Athens? Correct. Yeah, so they had buses that picked this up at like 4 a.m. or something. Oh, you did it as part of the official marathon. You did it as a race. Yeah. So that one, it is the actual race. I did that one by myself last summer, and I found sort of like you were talking about your room when I was fine up until I basically entered Athens and then all of a sudden I had to make traffic-related decisions.

That's where I struggled because it's like cognitively, you know, your ability to think, you know, it degrades with time. That's actually a great point on these runs is part of the challenge is making good decisions. Later, you know, as you get dehydrated or it's hot. and continue to make those good decisions. But for me, that's the fun of the 50K distances. There's probably a point where it's going to be really low, and you're going to be saying yourself, this kind of sucks. Or I habitually overestimate how fast I'll run something.

And that's particularly problematic if maybe you're out of cell phone service and you're telling your family, I'll be back at three and then they're not there at three and then show up at seven and they haven't heard for you for four hours. The best thing about all these journeys is there was always some point where things weren't going that well. And the thing that you need to keep in mind is I'll work through this. Like, I just need to drink some more water. I'll eat some gummy bears. Maybe I'll go stop at a cafe and why not have a coffee in a croissant and have some dates,

whatever it is, that it'll be better in 30 minutes. That for me is the number one thing to keep. keep in mind with the long distance running is it'll be really hard at some point. But you're clearly very trained and you're passionate about it and you'll come out the other side. And then that will be the moment that makes it feel very rewarding as you just took it in. He kept going and had a great experience. That's great advice. Every time you look at your phone, there's another chaotic headline.

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where you're talking to robots and you get in that endless loop. It's not fun for you and I, the customers. It's also not great for the company, right? They know they're not serving their customers well. When a person has to intervene, that person is dealing with someone who's mad at them. It's a whole system that I think is due for a rethink, and that's where 11 agents come in.

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.io slash stoic and see how 11 agents can fit into your workflows and help build experiences that your customers and employees will actually love. 11 labs.io slash stoic. 11 labs.io slash stoic. Last question for you because it must be, it was something I experienced on the Greece one. And as part of a sanctioned race or marathon or whatever, it makes sense that these people are all getting to this certain point and then they're out of gas and they collapse or, you know, like it's appropriate, you know, to be finishing here. I found when I finished in the Olympic Stadium by myself on an ordinary day and then, you know, started vomiting all over the place, people were like, what is happening? Who is this maniac, you know? when you finish a 50K or longer into a hotel lobby or whatever, and you're sweating through everything, you're dehydrated, you're crazy, you're foaming at the mouth or whatever.

Talk to me about finishing a race that nobody knows you're running. I'm so glad he brought this out. I think about this all the time, because I have a lot of these in my head of walking into hotel lobbies. One was at a small hotel in the black forest. I don't know if they had 10 rooms. I walk in, it's at night cold driving rain. The woman checks me in no differently than any other checking experience I've had.

Same thing in Laf Slovakia. I walk in there, super late, driving rain. Hello, can I see your passport? Here's your key. There was one in Portugal. I was up in Porto. It was a nice kind of boutique hotel. Same thing, check-in.

And she goes around to giving my key, and says, may I help you with your bag and grabs my backpack? And I was like, you do not need to touch that. Because again, that's all I have. Yeah. And I always think back to that. I'm like, is it this common?

I mean, literally not a single common. Like, where did you come from? Like, this person, they literally have this little backpack. Like I said, sweat it out. I'm dirty, driving rain, whatever it is. And they literally have no other expression other than just what's your name. Like, it's the most normal thing in the world.

So I've always wondered. I'm like, maybe it's not that unusual. Or maybe they're just good at not reacting to the craziest thing we've ever seen in their life. Maybe they see other crazy things. But that is like extremely kind, yeah, because I walk in these places. I don't know that I can think of a case where somebody was like, oh, my God, where did you come? Yeah, and it's like, you sort of want credit for it, you know? But then it feels weird to be like, you know, I just ran here.

And they're like, okay. I would be dying to ask me, like, where'd you come from? I just came from Austria. And they're like, I'm not even in that country right now. Well, that's where I was like 12 hours ago. But yeah, it's interesting. Coming across folks like that. And then I also imagine during the run, you're probably occasionally coming across other runners

and you're like, we're not doing the same thing. Let's just be clear. Yeah, that is very true. Well, what's fascinating about is how few. people because I have my website, ultra running destinations. So it's got almost 100 of these runs. How few people I cross paths within those runs?

And I don't know that I ever cross somebody. And I would see people. Like one of the things I was found like Europeans are not friendly on the trail. Like to you are like your two people in the middle of nowhere. I think you'd give a little high like, hey, what's up? Yeah. Just dead expression looking at it doesn't want to interact. And the U.S. people are generally like, hey, what's up?

But the few people I talked to, they were from the local area. didn't cross somebody doing a cross-country run. Yeah, you do see interesting things. Dogs and animals, other kind of things out there, but people were fairly absent. Because once you get a mile away from any trailhead in general, nobody's on it. There's not a mass of people, you know,

five or 10 miles from a population center on a trail in any cases. I mean, one of the things you find, this is why what you do so interesting is like, even the major cities, right? Like, if you get up at 6 a.m. and run around any major city anywhere in the world, you've got the thing, like, almost entirely to yourself. And it is the best way, like, my sort of travel philosophy is I try to bring my family everywhere I go, but I get up early. I run. I see the whole place. And then I read all the signs that I want to read, and I soak in

the things I want to see. And then, you know, sometimes we'll go back and look at those things. But it's like I feel like I already won the tourism game, you know, by the time I'm sitting down for breakfast that morning, everything else is gravy from there. I agree. And I only have one exception to this rule is DACA Bangladesh. Okay. It never stopped. The rush hour at 5 p.m. It was the same rush hour at 2 a.m. at 5 a.m.

But I did found a group of runners. So that's the other thing is there are runners everywhere on Earth. Yeah. I searched online. I found a group. It was this group called hashing. Have you heard of this hashing concept? No.

So it started, I guess, I think after the World War II, by some British folks. It's a running club that's all around the world called hashing. I've only done it once, I'd never heard of it. And I was searching online for running. It was actually an article about where not to run in Bangladesh, which was nowhere to run. I reached out to this person anyhow,

and they said, oh, there's a group run happening, put me in a WhatsApp group, and it was this hashing group, so it was mainly expats, And they were like 30 minutes outside of Doca, Bangladesh, which again is insane 24 hours a day. But then we're in a countryside running over bamboo bridges. Wow. So you're in one of the most densely populated cities in the world.

And then to your point, there is a part of it within 30 minutes. That's countryside. There's next to nobody. So, but I didn't know that this group existed and I was thankful that I found them in that spot because there was no hard to run. around the hotel. But I agree, you're in Manhattan at 5 a.m. You have the city. It's yours.

It's amazing, right? It's the best. Well, this is awesome. I appreciate the advice, and hopefully I can report back that I made it through.