RyanHoliday.net - Meditations on strategy and life
  • Home
  • About
  • Newsletter
  • Reading List
  • Blog
  • Best Articles
    • Archive
  • Speaking
  • Books and Courses
  • Contact
Home
About
Newsletter
Reading List
Blog
Best Articles
    Archive
Speaking
Books and Courses
Contact
  • Home
  • About
  • Newsletter
  • Reading List
  • Blog
  • Best Articles
    • Archive
  • Speaking
  • Books and Courses
  • Contact
RyanHoliday.net - Meditations on strategy and life
Blog

This Won’t Solve All Your Problems (Just Most of Them)

In March 2025, we found two ten-week old puppies dumped on the road near where we live out in the country.

One was white with spots. The other was mostly black with some white on her chest and paws.

Both were emaciated, covered in flea bites, and scared of the thunderstorm that was just starting. 

We took them home and as you can imagine our kids begged for us to keep them. I remembered many years ago reading about “the black dog bias”—that for some reason darker dogs are considered scarier and less likely to be adopted—so we decided to keep that one and found a home, almost immediately for the other. 

It was a good thing because my kids had fallen in love with “Oreo.” 

Like every parent of all time, I was assured that they would take care of her and walk her. And like every kid who has ever made that promise, mine have not exactly followed through.

But I’m not mad, because it means I have to take her for two walks a day (on occasion I succeed in bribing or threatening the boys to come too). Of all the ways Oreo has changed our lives, that’s been the best part. She’s “forced” me to do more of something I love to do. Something I know is really good for me, for anyone.

Walking is good exercise, of course. It burns calories. You get vitamin D from the sun. If the research is correct, apparently getting several thousand steps a day comes with all sorts of benefits for your health and longevity. But I don’t care about any of that. I don’t mind those things, but I walk for the philosophical and psychological benefits.

For centuries, thinkers have walked many miles a day because they had to, because they were bored, because they wanted to escape the putrid cities they lived in, because they wanted to get their blood flowing. In the process they discovered an important side-effect: it cleared their minds and helped them make better work. Literally, the name for the students of Aristotle was the Peripatetics—from the Greek peripatein, “to walk about”—because he did most of his teaching on walks.

Nietzsche’s, Thus Spoke Zarathustra came to him on a long walk. As he would later say: “It is only ideas gained from walking that have any worth.” The choreographer Twyla Tharp talks about going for “mindless mental wanderings” each day. Ernest Hemingway would walk along the Paris quais whenever his writing stalled. Charles Darwin built several walks into his daily schedule. The poet William Wordsworth walked as many as 180,000 miles in his lifetime—an average of six and a half miles a day since he was five years old! 

Even spiritual revelations seem to come on foot. Dorothy Day was a lifelong walker, and it was on her strolls along the beach on Staten Island in the 1920s that she first began to feel a strong sense of God in her life and the first flickerings of the awakening that would put her on a path toward sainthood. It’s probably not a coincidence that Jesus himself was a walker—a traveler—who knew the pleasures and the divineness of putting one foot in front of the other. Indeed, it’s no coincidence that many of the greatest expressions of faith and devotion involve long walks (i.e. pilgrimages) to holy sites around the globe.

The Buddhists speak of “walking meditation,” or kinhin, where movement after long periods of sitting, particularly through beautiful settings, can unlock a different kind of stillness than traditional meditation. In a beautiful letter to his bedridden and depressed sister-in-law, Søren Kierkegaard wrote: “Above all, do not lose your desire to walk. Every day I walk myself into a state of well-being and walk away from every illness; I have walked myself into my best thoughts, and I know of no thought so burdensome that one cannot walk away from it.”

In my life, I’ve been repeatedly gifted with ideas—from the muses, from my own subconscious, I don’t know—on walks. It was on a walk in Bastrop State Park with the kids when I got the idea for The Stoic Virtue Series. I’ve solved business problems and personal problems on walks. My wife can recognize it in my eyes and knows not to say anything when I return from a walk, rushing into the house and heading to the pile of notecards I have on the counter at all times. He’s probably come up with something…don’t interrupt or he’ll lose it and be a mess after. 

I’ll tell you what I’ve almost never thought—except a couple of times in the Texas summer—I have never returned from a walk and regretted it. Walks haven’t solved all my problems, but they rarely make them worse. And even when they haven’t changed anything, they’ve changed my mood—which is usually most of the problem anyway. 

Sitting at our computers, we are overwhelmed with information, with emails, with one thing after another. On a walk, the mind, relieved of all those inputs, can wander, drift, reflect, process, imagine, make connections, have ideas, or simply get a little peace and quiet.

Kierkegaard tells the story of a morning when he was driven from his house in a state of despair and frustration—illness, in his words. After an hour and a half, he was finally at peace and nearly back home when he bumped into a friendly gentleman who chattered on about a number of his problems. Isn’t that how it always seems to go?

No matter. “There was only one thing left for me to do,” Kierkegaard wrote, “instead of going home, to go walking again.”

And so must we.

Walk.

Then walk some more.

Anyway, I’ve got to go now. Oreo is scratching at the door. 

I’ll see if the kids want to come, but either way, I’m walking.

Tweet
September 3, 2026by Ryan Holiday
Blog

The Discipline Required To Create The Life You Want

You know, not everything has to be big. 

I realize that the impulse, especially when it comes to business, is to try to grow everything to the absolute biggest it can be.

This is not a new, but it’s certainly a defining trend of our age. After all, all this drama about data centers is being driven by hyperscalers—companies built around taking things that work and scaling them as far as they can possibly go.

But I hate that philosophy…or at least, it’s not what I practice in my life. 

In 2019, I could have started just about any kind of business. A bunch of my friends were starting tech companies. Others had been making a fortune investing, flipping real estate, trading crypto. 

I was the crazy one who decided to open a small bookstore in rural Texas. 

What’s crazier though is that the bookstore worked. And yet do you know what I get asked, probably once a week? “When are you going to open another location?” At least three struggling bookstores have reached out about us acquiring them. 

What strikes me isn’t that people ask—it’s how instinctively they ask. As if expansion were the only logical next step. As if the point of having one successful thing is to have two. Then four. Then forty.

On an episode of The Daily Stoic podcast a little while back, Nate Silver called it “the obsession with scale.” We were talking about how the venture capitalist mindset—where success is defined by scaling 1000x—has seeped into how ordinary people think about their work. About what it means to have a successful podcast. A successful newsletter. A successful creative career. A successful anything.

“In the content space,” Silver said, “VCs tend to analogize content creators or media startups to tech companies. When it’s actually more like running a restaurant. You can run one really nice restaurant. If you’re very lucky, you can even franchise that to a couple of locations and you can write a cookbook and you can get on Iron Chef or whatever. But it doesn’t have to scale beyond that. Unless you want to be a Chipotle or something, which is fine.”

It is fine if you want to be a Chipotle. There’s nothing wrong with building something large if that’s genuinely what you set out to do. But in my experience, most people actually don’t really think at all about what they’re setting out to do. They don’t sit down and consider what success would look like for them, what “enough” would feel like, what winning their particular game would mean. And because they’re not clear on what they actually want, they end up chasing growth indiscriminately. More followers. More subscribers. More platforms. More revenue. More locations. More, more, more—until eventually their thing collapses under its own weight. Or it succeeds and doesn’t fail…but it is an enormous, life-consuming burden. 

“Do Not Go Past The Mark You Aimed For” is one of the most important laws in ​The 48 Laws of Power​. It’s about knowing where you’re trying to go and when you’ve gotten there. It’s about knowing what game you’re playing and when you’ve won. It’s about having the discipline to choose the target and not blow past it. 

I think about this with myself. ​I write books about Stoicism​. If I wrote about something with more mass appeal or if I wrote romance novels or if I ghostwrote celebrity memoirs, maybe I would sell more books, make more money, or be known by more people.

But that wasn’t the mark I was aiming for. If it were, I certainly wouldn’t have chosen an obscure school of ancient philosophy as the means to try to get there.

Or, could The Daily Stoic make more money if we got into t-shirts and hats and supplements and energy drinks and cheap merch? Probably. Could we license the brand to some conglomerate and cash out? I bet we could find a buyer. But if the point of all this was to endlessly raise the ceiling on the amount of money coming in, I would have selected a different line of work a long time ago.

So many people think they have to live a life they don’t want for a long time so that eventually, off in the distant future, they can live a life they do want. They need to make millions or get famous or earn their big break. Then and only then can they…

I’ve always found it’s better to think about what my ideal ordinary day looks like. That, at least, is the mark I am aiming for: for that ideal ordinary day to be most of my days. When an opportunity comes along or I’m faced with a decision, I ask myself: Will this get me closer to that ideal or further away? Will it give me more of the days I actually want to have, or fewer of them?

A really cool job opportunity? I’ll consider it. But wait, it means moving my family to D.C., wearing a suit most days, being on someone else’s schedule—and I won’t be able to write much? Never mind. I could make a lot of money investing in startups? Sounds great. But I’d have to read pitch decks and go to meetings all day? You know what, I’ll pass.

You might ask: “But isn’t this a privileged way to live?” Yes, I do feel very privileged that for me happiness is relatively cheap. My ideal day doesn’t require me to be rich or powerful or important. It just requires that I be good enough at something to sell my services on the open market and strong enough to say no to things that are beyond my needs. That is a privilege, and it’s more accessible than we think. There are plenty of billionaires who don’t have it, plenty of ordinary people who have never lost it.

So it doesn’t take some enormous amount of money. Nor do you have to be famous or well-connected or wildly successful.

It takes discipline. 

The discipline to figure out what you actually want your life to look like.

The discipline to turn down cool, lucrative opportunities. =

The discipline to say no to the investors, the acquirers, the well-meaning people who have ideas for how you can really blow this thing up.

The discipline to not go past the mark you aimed for.

The discipline to not scale.

Tweet
August 28, 2026by Ryan Holiday
Blog

For Nearly 2,000 Years, This Is Who People Have Turned To When Life Gets Hard

The right book at the right time is a powerful thing.

In fact, it can change the whole course of your life.

Some time around the year 141 CE, the philosopher Junius Rusticus gave a young Marcus Aurelius a book from his own library: the lectures of a former slave named Epictetus. Marcus would remember the gift gratefully decades later, thanking Rusticus in Meditations “for introducing me to Epictetus’s lectures—and loaning me his own copy.”

Nearly two thousand years later, before the Vietnam War, James Stockdale had almost that exact experience as Marcus when he was given a copy of Epictetus by one of his professors at Stanford, Philip Rhinelander.

Neither Rusticus nor Rhinelander could have known just how consequential those recommendations would become. Marcus would rely on Epictetus as he became the most powerful man in the world. Stockdale would rely on him after his plane was shot down over North Vietnam and he spent seven and a half years as a prisoner of war.

There’s another impressionable young person whose life was changed by someone recommending Epictetus.

Who?

Me!

When I was 19 years old, I was invited to a small, private summit of college journalists that Dr. Drew, then the host of Loveline, was hosting. After it ended, he was standing in the corner and I cautiously made my way over to nervously ask if he had any book recommendations. He said he’d been reading a book called Discourses by a Stoic philosopher named Epictetus and that I should check it out.

I did. And nearly twenty years later, I’m still reading him, quoting him, writing about him, and coming back to his ideas.

What I love about Discourses is that it is not some dense academic philosophy book filled with abstract arguments that have very little to do with real life. It’s the opposite. Epictetus never wrote anything down. Discourses comes to us from one of his students, who tells us that “whatever I used to hear him say I wrote down, word for word, as best I could, as a record for later use of his thought and frank expression.” So what we have is essentially a collection of conversations—Epictetus going back and forth in real time with his students.

It’s an unusual book, to be sure. And as powerful as Epictetus is, he’s not the easiest to get through. He did not suffer fools easily. He wasn’t afraid to call his students foolish for not understanding him or for missing the point. I think that’s one of the reasons I didn’t immediately take to Epictetus, and I know it’s why many people over the years have been turned off by him. He’s blunt, meanders a bit at times, and can be a bit of a struggle to understand at first. (FYI: That’s why we made the Daily Stoic How To Read Epictetus Guide—a digital companion to Discourses that gives you the context and guidance to better understand—and learn from—this incredible teacher).

But the pursuit of wisdom isn’t supposed to be painless. “The philosopher’s lecture hall is a hospital. You shouldn’t walk out of it feeling pleasure, but pain, for you weren’t well when you entered.” This from a guy uniquely equipped to speak about how to handle hardship. Unlike so many philosophers who spoke about hardship and struggle from positions of wealth and privilege, Epictetus experienced difficulties few of us can even imagine.

He was born into slavery in a Greek province of the Roman Empire in what is now modern-day Turkey. His name—Epiktetos—means “acquired one.” And even by Roman standards, his master was cruel and violent, at one point twisting Epictetus’s leg with all his might. As a punishment? As a sick pleasure? Trying to get a disobedient young kid to follow instructions? We don’t know. All we know is that Epictetus calmly warned him about taking it too far. When the leg snapped, Epictetus made no sound, he uttered no tears. He smiled and looked at his master and said, “Didn’t I warn you?”

For the rest of his life, Epictetus walked with a limp. But he remained unbroken by the incident. “Lameness is an impediment to the leg,” he would later say, “but not to the will.” He would choose to see his disability as only a physical impairment, and in fact it was that idea of choice that defined the core of his philosophical beliefs. He called it our “first job” in life. It was simply this:“to divide and distinguish things into two categories: externals I cannot control, but the choices I make with regard to them I do control.”

Our judgments. Our attitudes. Our wants. Our desires. Our opinions about what has happened to us. Our choices about how we respond to what has happened to us. Those are up to us.

Life was like a play, he liked to say, and if it was the playwright’s “pleasure you should act a poor man, a cripple, a governor, or a private person, see that you act it naturally. For this is your business, to act well the character assigned you; to choose it is another’s.”

One of my personal favorites is Epictetus’s idea that every situation has two handles—“one by which it can be carried, and one by which it can’t.” When bad news comes, do I grab the handle of despair or the handle of action? When I’m slighted, grievance or grace? When things feel uncertain, fear or preparation?

There is another wonderful line from Epictetus that I think of every time I see someone get terribly offended or outraged about something—and that I try to think about when I get upset myself. “If someone succeeds in provoking you,” he said, “realize that your mind is complicit in the provocation.” Whatever the other person did is on them. Whatever your reaction is, that’s on you.

The Discourses are full of passages like this, little arguments and anecdotes that force a shift in perspective. Epictetus never actually wrote any of them down. They come from one of his students, Arrian, who tells us that “whatever I used to hear him say I wrote down, word for word, as best I could, as a record for later use of his thought and frank expression.”

Stoicism as a philosophy was made to be kept in hand, always at the ready. And it is the title of Epictetus’s Enchiridion (a kind of “greatest hits” of his teachings collected at the back of many editions of Discourses) that best shows this. It comes from a Greek word meaning “held in hand” or “have at hand,” and at the time, it often referred to a hand-knife or dagger. Arrian’s idea in choosing the title was that Epictetus’s teaching worked the same way. They were something you could keep at hand and reach for in difficult moments.

“If you didn’t learn these things to demonstrate them in practice, what did you learn them for?” Epictetus pointedly asked.

Stockdale had spent those years before the war with his Epictetus books on his bedside table, several hours each week buried in them. Then on September 9, 1965, his A-4 Skyhawk was shot down over North Vietnam. “Five years down there, at least,” Stockdale said after ejecting from his plane. “I’m leaving the world of technology and entering the world of Epictetus.”

It turned out to be seven and a half years in a brutal Vietnamese prison, where Stockdale was repeatedly tortured and spent long stretches in isolation. He would later credit Epictetus—and all those hours spent buried in his books—with helping him survive it.

Stockdale wasn’t alone to test Epictetus’s ideas in “the laboratory of human behavior,” as he liked to put it.

Frederick the Great carried Epictetus with him into battle. Thomas Wentworth Higginson was reading him as he raised and led one of the first black regiments for the Union in the Civil War. Toussaint Louverture, the leader of the Haitian Revolution, studied him too as he rose up against Napoleon. And Theodore Roosevelt took a copy of Epictetus with him on his brutal “River of Doubt” expedition in the Amazon.

“Lent to me by my friend Major James A. Shipton and carried by me through my South American journey, including the exploration of the River of Doubt: Theodore Roosevelt, Feb 8th 1915”

I like to say that Epictetus is your favorite philosopher’s favorite philosopher. Like the way we sometimes talk about “your favorite rapper’s favorite rapper” or “your favorite comedian’s favorite comedian”—someone who isn’t necessarily the biggest name, but who is revered by those in the know.

Epictetus is like that. Someone who should be much more widely known and read—because when he is, he changes lives.

He changed Marcus’s.

He changed Stockdale’s.

He changed mine.

And he can change yours.

P.S. As I mentioned briefly above, if you do decide to read Discourses (you can pick up my favorite translation here), we put together the Daily Stoic How To Read Epictetus Guide to help you best navigate it, and it will be 30% off with your purchase of the book this month. It’s 14 in-depth modules that distill all of my reading, rereading, and rabbit-holing of Epictetus into a kind of roadmap designed to help you get out of the book in a few weeks what took me nearly twenty years.

August has been Epictetus Month over at Daily Stoic, where thousands of us have been reading and discussing Epictetus together. And on August 27th, I’m hosting a live Epictetus Q&A, where I’ll take your questions.

Just get the guide before August 26th to receive your invite to the Q&A.

I hope to see you there!

Tweet
August 20, 2026by Ryan Holiday
Page 1 of 3101234»102030...Last »

“If you only read the books that everyone else is reading, you can only think what everyone else is thinking.” - Murakami

© 2018 copyright Ryan Holiday // All rights reserved // Privacy Policy
This site directs people to Amazon and is an Amazon Associate member.