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

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1:50Ryan Holiday: 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 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.

2:26Ryan Holiday: 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 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.

3:04Ryan Holiday: And so he was always in these different European capitals, 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 ultra marathons along the way. It was totally crazy. It's the only one I'd found that done anything like this. So I go into 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 bonus episode here.

3:44Ryan Holiday: 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 ultrarunningdestinations.com to check out his 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.

4:26Ryan Holiday: 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. You want to see me in Nashville, in Boston, in Philly, in DC. 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 dailystokelive.com. Tell me about what makes a person get off a flight and then just run 53 kilometers into a city. Whatever possessed 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.

5:12I 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, What's a great counterbalance to that was to go do a journey of my own on the weekends. And I kind of had this goal to visit every European country and ended up mostly doing that.

5:31Ryan Holiday: 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 of folks that planned trips for people. And I found them online and said, hey, I'm coming to Bulgaria. Would you help me plan 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.

6:07They're generally always 50K, so 30 miles.

6:09Ryan Holiday: So one time I misplanned and it was like 45 miles, something like that. But I didn't like to over plan. Like there's an art to knowing how to get in and get out. You just 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.

6:47It'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 Merino wool pants, a Merino wool shirt, Merino wool underwear. So I had clothes I could wear when I wasn't running.

7:09Ryan Holiday: Yeah. And then I would have my running clothes, which would be a pair of like windbreaker pants, my shorts, my shirt, a long sleeve shirt. And then I'd have an extra 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?

8:01Yeah. It completely changes your 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 traversed 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.

8:41And it's largely unchanged since I think it was built. So I guess maybe that surprises how enduring it is.

8:49Ryan Holiday: The Appian Way is mind-blowing to consider, one, that 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. I mean, it's lined with tombs, right?

9:28Ryan Holiday: 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, you know, 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? What would you remember about that run? For whatever reason, one of the most memorable parts was getting to the airport. So I flew in on, I think, Ryanair.

10:01So it goes on to another smaller airport outside the city. The fueling for the run was some coffee. I think I had a couple of cappuccinos and some croissants. Probably put a bunch of Nutella in there.

10:13Ryan Holiday: And gummy bears? You like gummy bears, right? I love gummy bears. Because gummy bears and Twix, you can get anywhere. I have yet to find a place on the globe where you can't get gummy bears and Twix. So that's what's in my pack. But I love European coffee. I love things like croissants. 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.

10:54and 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 ruined. They're more recent than the Roman era, but these ruins of folks that had estates with, again, grand entrances and now it seemed that it hadn't been populated in a very long time. But yeah, a very kind of inuspicious start of a relaxing morning with some coffee and kind of 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.

11:32It 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 is time spent enjoying the start and not really thinking about the finish is kind of enjoying it.

11:47Ryan Holiday: 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's 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.

12:26I 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. 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 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 i just stand there and be like i mean when did 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 you'd really look at those details something that you you kind of rarely do because there's I'm by myself there's not 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 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 a single track trail and seeing a path.

13:43And that's, I've always wondered like, what was that path there for?

13:47Ryan Holiday: 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 it 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.

14:17Ryan Holiday: And they said that the cobblestones and those sort of paving stones, 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 particularly on that run the there are points where the the road are extremely extremely irregular so it was much more comfortable to run in the grass but a lot of that main path there it is kind of park grass-like area and most of my time running through that.

15:05And I find that just as keeps your body out of the same groove because kind of not what we 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 opinion. That's what leads to the injuries. And I've been fortunate not to be injured. And I think part of that is running through the grass or in the dirt along the path of the gravel.

15:27Ryan Holiday: The irregularity is kind of the 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, 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, I had a friend actually asked me one time, he's like, what do you look at?

16:00He'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, there might be a hole or something else that you need to think about. So it definitely forces you in the moment much more than the road running where you can kind of just turn it off.

16:20Ryan Holiday: 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 in 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?

16:56basically taking out. What's the top site that you're looking forward to soon?

17:02Ryan Holiday: 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 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 handful of sites that I want to do.

17:38Ryan Holiday: 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 and 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 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 that's kind of that I did.

18:12Ryan Holiday: I did a similar thing in Greece this summer. I was going to ask you, did you do one of these in Greece or? 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 us 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 Rome one.

18:47Ryan Holiday: 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. It was 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 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 to yourself, this kind of sucks. Or I habitually overestimate how fast I'll run something.

19:30And 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 not there at three and then they show up at seven and they haven't heard for you 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 and a croissant and have some dates, whatever it is, that it'll be better in 30 minutes.

20:07That for me is the number one thing to 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'll be the moment that makes it feel very rewarding as you just, you took it in and kept going and had a great experience.

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23:08Ryan Holiday: 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.

23:51Ryan Holiday: Talk to me about finishing a race that nobody knows you're running. I'm so glad you brought this up. 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 check-in experience i've had same thing with slovakia i walk in there super late driving rain hello can i see your passport can like 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 give me my key and says may i help you with your bag and grabs my backpack.

24:41And 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. I'm like, where did you come from? 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?

25:08Ryan Holiday: 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 they've ever seen in their life. Maybe they see other crazy things. But that is like extremely common 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 for them to ask me, like, where'd you come from?

25:39I 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.

25:50Ryan Holiday: And then also I 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 it is how few people, because I have my website, ultrarunninestinations.com, so it's got almost 100 of these runs. How few people I cross paths with in those runs. And I don't know that I ever cross somebody. And I would see people. Like, one thing I always find, like, Europeans, they're not friendly on the trail. Like, so you're like, you're two people in the middle of nowhere.

26:23I think you'd get a little high, like, hey, what's up? Yeah. Just dead expression looking at and 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.

26:49Ryan Holiday: Right. There's not a mass of people, you know, five or ten 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? If you get up at 6 a.m. and run around any major city anywhere in the world, you've got the thing almost entirely to yourself. And it is the best way. 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.

27:30Ryan Holiday: 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 Dhaka, 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 find 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 World War II by some British folks.

28:07It'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 Dhaka, Bangladesh, which again is insane 24 hours a day. But then we're in a countryside running over bamboo bridges. So you're in one of the most densely populated cities in the world.

28:44And then to your point, there is a part of it within 30 minutes. That's countryside. Yeah. There's next to nobody. So, but I didn't know that this group existed and was thankful that I found them in that spot because there was nowhere 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.

29:08Ryan Holiday: Well, this is awesome. I appreciate the advice and hopefully I can report back that I made it through.