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RyanHoliday.net - Meditations on strategy and life
Blog

Why I Ran A 50K Through Rome Alone (And What It Taught Me)

In the middle of Rome, there stands one of the great trophies of history, the Column of Marcus Aurelius.

The nearly 100-foot monument was put up to commemorate Marcus’ victories during the Marcomannic Wars. It is covered in carvings depicting scenes of his armies marching, crossing rivers, laying siege to cities, fighting battles.

It’s a towering celebration of Marcus’ achievements, literally carved in stone.

But you know what? Marcus didn’t get to bask in all this glory. He died before the column was finished.

And then, in the sixteenth century, Pope Sixtus V had the monument restored and put Saint Paul on top instead. They even added a new inscription at the bottom, attributing all of the victories to the wrong emperor.

I was thinking about all of this a couple months ago, standing beneath the very monument. It was a little over 5 kilometers into what would be the furthest I’ve ever run in my life—50 kilometers (31 miles) through the streets of Rome, stopping at some of the most important Stoic sites in the world along the way.

Why did I run a 50K by myself through the streets of a foreign city during the hottest part of the year—literally the hottest it has ever been in Europe?

Because it’s hard.

And doing hard things is good for you. That was the whole point. Do we do hard things because we want to impress people? Because we want to beat other people? Because we want a medal or a trophy?

No. As Marcus’ victory column is a pretty good reminder, doing things for a trophy is a terrible reason to do things.

That’s why I like doing challenges like this, more than races or competitions. There was no starting gun for this run, no official course, no medal waiting for me at the end. I picked the start time. I picked whether it would start at all…and certainly whether I would finish. I like things where the victory is what I get out of it.

A few kilometers after the column, I got lost. I did a one-mile loop in completely the wrong direction. I was already trying to run farther than I had ever run before and now I’d added an extra mile. But I knew something like this was going to happen. When we do hard things, we have to be prepared for them to be harder than we’re anticipating. If you go into something thinking, This is all the gas I have in the tank. This is all I’m capable of doing. I need everything to go right, you’re in a really vulnerable position. Everything is not going to go right. As Seneca said, the unexpected blow lands heaviest. If I was lost and disoriented and mad at myself right then, this would have been harder than it was.

Instead, I figured out where I screwed up, turned around and kept going. What else are you going to do? From there, I ran up to the Campidoglio and the equestrian statue of Marcus Aurelius, past the Colosseum, through Circus Maximus and eventually out toward the Appian Way.

Almost thirteen miles in, I stopped at what is supposedly Seneca’s tomb. We don’t know for certain. There are no inscriptions identifying it, and two thousand years is a long time and stuff starts to disappear. The last time I had been there was about thirteen years earlier. I had a picture of myself from that trip.

We see ourselves every day, so the passing of time can be invisible to us. Then you come back to a place you haven’t been in a long time. I looked at that old picture of myself. I feel the same. I feel great. I feel better than I did then. But you look at it and you go, Oh, I have more gray hairs now. I have more wrinkles. I can see the last ten years. Marcus Aurelius talks about time being this vicious, unrelenting, ceaseless, almost merciless flow of events, faster and faster and faster, taking us with it.

Standing there at Seneca’s tomb, I wondered if he knew that his plays would still be read two thousand years later. I wondered if he knew that his grave would get worn down by events and eventually forgotten.

By the time I got to the turnaround point, I was 15.64 miles in. I felt pretty good. I was hydrated (Rome is filled with little fountains of fresh drinking water). The shade had been nice. But it was getting hot and I was way behind schedule. It was already 8:40 in the morning, three hours and forty minutes after I’d started.

I hadn’t quite budgeted for how long all the stopping and filming was going to take. Whenever I’m preparing to do something challenging, I like to try to talk to and learn from someone who has done something similar before. Googling around before this run, I found a guy named Luke Tuttle who had run 53 kilometers into Rome and written about it on his blog. So I reached out. I had a million questions for him, and the conversation was so great that we turned it into an episode of the podcast.  He gave me some really good advice: Just let it take however long it takes. You’re not gonna be glad you rushed through it. Take your time. Stop. Admire the sights. Soak it in. If you have to walk, you have to walk.

The point isn’t to win at your hobbies. The point is to do it, to have fun doing it, to experience it, to be there for it. You don’t rush through other things that are pleasurable, and then for some reason, physical activity we try to get done as fast as possible.

It was funny: I wasn’t racing anyone. There wasn’t even a race. Other than trying to beat the full heat of the sun it was impossible to be “behind schedule.” So I took a break, turned around and started running back.

Eventually I got to the point where there were seven miles left. You know you’re doing something hard when you think, only seven miles left. That’s one of the great things about doing hard things. You push yourself, you raise your threshold higher and higher until what used to seem like a lot now only seems like a little.

A few miles later, I’d officially done a marathon. I still had five-ish miles to go. At that point I was thinking about something Epictetus said: Whatever difficulties you face, understand what resources you have inside you. How was I going to get through the last five miles? With the same willpower and strength and training that got me through the first twenty-six.

Honestly, this is my favorite part. They say you’re not really pushing yourself until you get to your limits. It’s after you get tired and keep going that the muscle and strength and fortitude are earned.

It’s a little like working on a book. The first two-thirds, sometimes even the first 80 percent, is the really hard part. You don’t know if you’re going to make it. You don’t know if the thing is going to work. Then you reach a point where you know you’re going to make it as long as you don’t quit. You’ve crossed most of the difficulties off. You have some momentum. You’re in a rhythm.

You have this sense of what you’re capable of because of what you’ve just done. You just gotta see it through.

Somewhere around mile 29.5, I lost it. That was apparently my limit. I was fucking dying at the end. Whatever graceful ideas I had about finishing strong disappeared. I staggered into this little restaurant stand alongside the Tiber and asked if they had water and took Apple Pay. They were incredibly confused about this person stumbling about and slurring his words. I drank two water bottles and then basically  limped the rest of the way.

The whole thing took much longer than I thought. It was much harder than I thought. I got lost. I stopped more than expected. The last couple miles took everything I had.

And then my son popped out from an alleyway and spontaneously joined me, which was just the best. Some thirteen years earlier, somewhere along the Appian Way, I had asked my wife to marry me. And now I was back, finishing this run on that same ancient road with my nine year old son jogging along for the last couple hundred yards.

That’s why we do hard things.

I started the morning knowing I was going to try to run further than I ever had in my life.

Six and a half hours later, I knew a little bit more about myself.

About where my limits are.

About what I’m capable of.

About what I’ve got in the tank.

That was the trophy.

And that one I get to keep.

September 29, 2026by Ryan Holiday
Blog

If You’re Trying To Do This Fast, You’re Doing It Wrong

Before we get into today’s piece…tomorrow I’m hosting a live Q&A session with everyone in the Read to Lead course over at Daily Stoic. Today is the last day to sign up and get your invitation—I hope to see you there! 

Reading is a good thing. 

Every book teaches us something, makes us a little smarter and wiser, right?

And not enough people read enough…

So learning how to read faster is the answer?

No, it’s not. 

Speed reading is not only a scam. It’s missing the point. 

I get this a lot. Because I talk about reading quite a bit, people assume I am a speed reader. I’m not. Across all the other great readers I’ve gotten to know and all the great readers throughout history I’ve studied, I can’t think of anyone who attributed how much they read to how fast they read. I can’t think of a single example of a “speed reader.” 

I just spend a lot of time reading.

Because it’s important. Because I enjoy it. 

I like food. I like music. I don’t rush through those either. Nobody tries to have sex faster, do they? Don’t most people try the opposite?

But here we are with people listening to audiobooks at 2x or 3x speed. Here we are with speed-reading courses that will teach you special techniques to blaze through books. Here we are with rapid-reading apps that flash words at you faster and faster to up your words-per-minute rate. Here we are with people hung up on how many books they read instead of how much they get out of the books they read.

Great readers take their time. Great readers read deliberately. Great readers read actively. I think of people like Joan Didion and Emerson, who filled hundreds of commonplace books with handwritten passages and quotes and ideas from the books they read. People like Montaigne and John Adams, who were lifelong producers of “marginalia,” covering the margins of their books with notes, comments, questions, disagreements, free-form musings, curiosities they wanted to investigate further. People like Major George Patton and Octavia Butler, who were dyslexic and had to struggle just to make sense of the words on the page and still were voracious readers.

People who read a lot of books spend a lot of time reading. There’s no way around this. “The best way to read quickly,” as Tyler Cowen has said, “is to read lots. And lots…Reading quickly is often, in a margin-relevant way, close to not reading much at all.” 

In Wisdom Takes Work, I tell a story about a samurai warrior named Banzo, who sought an education so that he could impress his father. Told by a great teacher that mastery would take ten years, he was aghast.

“I can’t wait that long. What if I work extra hard?”

“OK,” the master said. “Thirty years.”

“But I will do whatever it takes to make it go faster,” Banzo pleaded.

“In that case,” the master said, “it shall take seventy years. A student in a hurry learns the slowest.”

The whole point of reading is that it’s hard, but that the hard is worth it. The whole point of a book is that there is a lot in there and it will take time to get it out. There is a payoff and that payoff is priceless wisdom. In one of the first passages in Meditations, Marcus Aurelius wrote that one of the most important lessons he learned in life was to invest in his education and to always regard “the resulting costs as money well-spent.” 

That seems to be another thing great readers have in common: they regard all the time (and money) spent reading as well-spent. A big part of how I manage to read as much as I do has come down to identifying as a professional reader, and by that I don’t just mean I read as part of my job as a writer or a bookstore owner, but that I see reading as my job.

It makes me a better person. It makes me a better parent. It makes me a better husband. It makes me a better boss. It makes me better at everything I do. So I take it seriously. I invest in it.

That’s the idea behind Read to Lead: A Daily Stoic Reading Challenge—which we are re-launching right now. It was designed for people who want to take their reading more seriously. Not to read faster. Not to sound smarter. Not to impress people with how many books they’ve finished. But to actually get better. To accumulate a mass of true wisdom—that you can turn to and apply in your actual day-to-day life.

There are no shortcuts, no hacks, no way around it. 

To be a great reader, you spend a lot of time doing it—slowly, patiently, attentively, without trying to make it go faster, without being in any hurry.

P.S. If you want to learn to get more out of every book you read, Read to Lead is for you!

It was painstakingly designed to distill everything I’ve learned about being a great reader to help you learn in a few weeks what took me nearly two decades to figure out.

Across 15 challenges (at a pace of one every three days), I’ll walk you through the best of what I’ve learned about reading: how I read, how I choose what to read, how I retain more of what I read, how I work my way through difficult books, and—most importantly—how I take what I read and put it to use in my actual life.

Along with the 15 challenges, you also get access to a private community where you can connect with fellow readers, an instant 20% discount at The Painted Porch Bookshop, and, of course, lots and lots of book recommendations.

Check it out here!

September 22, 2026by Ryan Holiday
Blog

I’m Sorry But There’s No Shortcut for This (And That’s a Good Thing)

It’s clearly a timeless tendency because Seneca tells us a story about it from two thousand years ago. 

People have always wanted to get something for nothing. They’ve always wanted to get the results without doing the work. 

Especially when it comes to knowledge. 

“Wanting to appear a well-read man,” Seneca writes about a rich but lazy Roman named Calvisius Sabinus, “he thought up the following short cut: he spent an enormous amount of money on slaves,” each one tasked with mastering a different body of work. 

One had to know Homer by heart. Another had to master Hesiod. He had a slave for Sappho, another for Pindar, and one for Simonides—one for each of the ancient Greek poets that an upper-class Roman was supposed to know inside and out.

At dinner parties, Sabinus kept these learned but enslaved Romans at his elbow, ready to feed him quotes, references, and facts to impress his educated friends. And he would insist, Seneca tells us, that summoning knowledge on demand from one’s staff was no different from summoning it from one’s mind. Indulging this notion that any readily available capability was effectively one of your own, a friend suggested Sabinus take up wrestling.

“But I am weak and frail,” Sabinus replied. 

“Don’t say that,” the friend teased. “Consider how many perfectly healthy slaves you have!”

I know it isn’t, but I like to think of this as a parable about AI. It would be nice if someone could do your learning for you, if something could do your thinking for you…but that’s just not how it works. 

Even now. Even as LLMs can do incredible things. 

Because as I’ve said before, the point isn’t to have the information, it is to be the person who has done the work to get the information. You can pay someone to lift something for you…but that won’t make you strong. 

I think about this with my own writing. I am in the middle of working on a biography of someone who wrote thousands of letters, gave hundreds of speeches, sat for oral histories, published his own books and was the subject of countless newspaper reports, classified documents and contemporaneous accounts…and so did the people he was closest to or worked for and with. It would be wonderful if I could just download this into my brain—or I guess my research assistants’ brain—but there is really no way to escape the great Robert Caro’s dictum that you have to “turn every page.”

So my researcher can help me track stuff down, scan stuff, put it in little binders, but ultimately, I have to touch it all. Every damn page. I have to read it all. 

But I don’t mind. I don’t mind because 1) Reading is amazing. I love doing it. Why would I want to skip the best part of my job? 2) Because it is my job, I’m pretty good at it.  

I was lucky in that I had someone teach me how to read well. Marcus Aurelius talked about how “mastery of reading requires a master.” For Marcus, his teacher Rusticus was that master—the one who taught him “to read attentively—not to be satisfied with ‘just getting the gist of it.’” 

For me, Robert Greene was my master. I started as his research assistant, and his rigor as a reader and researcher was legendary. He taught me to go way beyond the “gist.” He taught me to hold what I read—and what I brought him—to a very high standard. Finding the perfect quote or story for whatever he was working on wasn’t enough. Where did it come from? What was the context? Was the source itself legitimate? Does it hold up across other sources? Was I settling for the first thing that seemed relevant or confirmed what I wanted? 

He sent me down rabbit holes. He asked me to go find papers and old works that were, in the days before Google Books, harder to locate. He had me transcribe interviews (something no one does anymore). He introduced me to writers and thinkers I had never heard of. He taught me how he used notecards and how he organized his library. Most of all, he modeled for me what a disciplined, curious and well-read person can be. 

To be a great reader, it’s not enough to read—you have to question, challenge, verify, and mark things up. You have to put books through the wringer and authors on trial. You have to go chase things down, follow footnotes, look up references, look up words you don’t know. You have to have a practice of capturing information and organizing it so it can be drawn on when you need it later.

Sadly, too many people are not taught how to be great readers—and never find the masters who can show them. That’s the idea behind Read to Lead: A Daily Stoic Reading Challenge—which we are re-launching right now. It was painstakingly designed to distill everything I’ve learned about being a great reader—from Robert, from trial and error, from the habits of other great readers I’ve gotten to know, from studying how history’s greatest readers read—to help you learn in a few weeks what took me nearly two decades to figure out.

Read to Lead takes place across 6 weeks at a pace of one challenge every three days (15 challenges and more than 30,000 words of exclusive content), with each challenge built around a specific practice for becoming a better reader. And no, there are no hacks, tricks, or shortcuts. You will not learn how to be a speed reader—that’s a scam. We are not going to show you how to use AI to get out of having to pick up a book. We are not going to tell you to play your audiobooks at 3X speed. We are not going to show you how to shut off that little voice in your head so you can supposedly race through pages faster.

The whole point of reading is that it’s hard, but that the hard is worth it. There is a payoff and that payoff is priceless wisdom. Reading is not about impressing people or winning some game of mental gymnastics. It’s not about winning trophies for your shelf. It’s not about collecting random pieces of information. It’s about accumulating a mass of true wisdom—that you can turn to and apply in your actual day-to-day life.

Valuable things are usually hard-won. Wisdom, a sound and strong mind, is one of them. “The greatest educational fallacy,” James Stockdale would say (himself sent to Stanford as an adult, where he learned to think critically and philosophically), “is that you can get it without stress.” 

No, the road to wisdom is long and rocky.

It’s one beset by obstacles, dead ends, and pits of despair.

One with staggering peaks and terrifying wonders.

One where there is always more ground to cover.

One that, above all, you cannot have anyone—or anything—else travel for you.

P.S. If you’ve never had a Rusticus or a Robert Greene show you how to be a great reader, I tried to build Read to Lead to give you a way to learn from those kinds of masters.

Across 15 challenges (at a pace of one every three days), I’ll walk you through the best of what I’ve learned about reading: how I read, how I choose what to read, how I retain more of what I read, how I work my way through difficult books, and—most importantly—how I take what I read and put it to use in my actual life.

Along with the 15 challenges, you also get access to a private community where you can connect with fellow readers, an instant 20% discount at The Painted Porch Bookshop, and, of course, lots and lots of book recommendations.

And I’ll also be hosting a live Q&A session on September 23 (just sign up by September 22 to get your invitation). It’s one of my favorite things to get the chance to talk about all things books and reading with everyone in the course.

I’d love for you to join us!

September 16, 2026by Ryan Holiday
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“If you only read the books that everyone else is reading, you can only think what everyone else is thinking.” - Murakami

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