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RyanHoliday.net - Meditations on strategy and life
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.

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!

August 20, 2026by Ryan Holiday
Blog

This Is Why We Opened A Banned Books Library (In Rural Texas)

One of my kids’ favorite books is I Need a New Butt. 

I don’t want to spoil the plot, but he needs a new butt not for any culture-war reason but because his has a crack in it. That’s funny, especially if you’re four or five or six or seven.

My boys love the sequels too, I Broke My Butt! and My Butt Is So Noisy!, which I’ve read to them many, many times. They’re funny and silly and ridiculous and creative. And they do what good children’s books are supposed to do: they help kids develop a love of books. 

Back in 2022, an assistant principal in Mississippi named Toby Price read I Need a New Butt! to a group of second graders. Then—gasp—some of the kids started saying the word “butt” a lot. So Price was fired. Seriously. He sued for wrongful termination. He spent a fortune on legal fees. The school district spent a fortune on legal fees. Eventually, he won and was reinstated. Everyone lost, including the taxpayers and the kids. As Price put it, “If you limit the books kids have, you limit the person they become.”

And this wasn’t some isolated bit of insanity. A little more than an hour from where we live in Texas, some crazy people in Llano County became fixated on getting the Butt books removed from the public library, calling them “grooming stuff.” The campaign spread, more books disappeared, and a librarian who resisted what was happening was eventually fired. 

Hitting even closer to home, the high school my sons are likely to go to here in Bastrop was in the news not long ago for challenging a book called Out of Darkness, about segregation in a Texas oil town in the 1930s. More comically, another parent angrily protested an example of gay sex from a book called Lawn Boy by Jonathan Evison at one of our school board meetings in September…but as the school librarian later pointed out, the school doesn’t even carry that book. The mother had confused it with another book literally about a boy who mows lawns. 

So I get a little frustrated when I see people say that book banning isn’t a real thing. The whole point of school—and libraries—should be introducing kids to books that make them laugh, make them think, and show them that books can be provocative and transgressive and interesting and creative.

This is exactly what I was going to say when I was supposed to speak at the U.S. Naval Academy last year. If you remember, my talk was cancelled moments before I went on stage because I was going to address the fact that the Academy—at the direction of the president and Secretary of Defense—had removed hundreds of books from its library for being “too woke.” (I wrote a whole NYT article about it). These are our warriors and they’re being told what books they can and can’t check out from a library?

Again, this is why I get upset when people say book banning isn’t real. 

The degree to which people will do mental gymnastics not to face this is crazy. Oh, it’s not a ban if they are just restricting access. Oh, it’s not censorship, they are just making sure it doesn’t get in the wrong hands (Sir, you’ve just described censorship). Apparently, if a book is available anywhere, it’s not actually banned? Tell that to the librarian who got fired. Tell that to all the educators being threatened with fines or even prison time for giving students access to certain books. In the antebellum South, Uncle Tom’s Cabin was banned and criminalized. The fact that you could still buy it in Boston doesn’t cancel that out. When the Catholic Church banned—and burned—books, was it not a big deal because there were still Protestant countries? 

With this deranged campaign spreading through schools and libraries around us, I started thinking about what I might be able to do about it. We’ve had this extra space in the building next door to The Painted Porch that we’d been trying to figure out what to do with for a while. Well, we figured it out. 

We turned it into a free lending library for banned books. After months of planning, designing, collecting books, and building the space out, the Banned Books Library opened a few weeks ago. My hope is that it can serve as one small counterblow against this deranged book-banning impulse spreading across the country.

Every book in the library has been banned or challenged somewhere. Some were removed by school boards. Some were outlawed by governments, burned by mobs, denounced by churches, dropped by publishers, or struck from the shelves of libraries, universities, and military academies. Some are great books. Some are strange books. Some contain ideas I agree with. Some contain ideas I don’t. That’s the point. A library is not an endorsement of every book inside it. Reading something is not the same as agreeing with it.

Like many public school kids, I was assigned Ray Bradbury’s Fahrenheit 451 in high school. I remembered the book as a warning against totalitarian censorship by the government. It was only later, rereading it as an adult, that I realized Bradbury was depicting something much more insidious. As Captain Beatty explains to Montag, censorship was what the people wanted. This horrendous burning of books hadn’t been forced on them by a tyrant. They had chosen it. One group didn’t like one book. Another group didn’t feel good about another. So burn it. Make everyone comfortable.

Bradbury’s message is a much more salient warning to modern Americans than many of us are ready for upon first reading. America is, and always has been, in less danger of top-down Chinese- or Soviet-style suppression and much more vulnerable to short-sighted or even well-intentioned democratic censorship. People are willing to ban a book because of what they think might be in it, or because of what someone else said was in it.

It’s almost beyond irony that that book itself has been challenged or banned in some schools. But that’s no more ironic than the fact that in 2024, the ACLU had to file a lawsuit to restore access to 1984 in a Colorado school district. 

Look, reading something is not the same thing as endorsing it. You can wrestle with a book. Challenge it. Disagree with it. Learn from it. In the fall of 1961, Commander James Stockdale began a course at Stanford on Marxist theory. “We read no criticisms of Marxism,” he later recalled, “only primary sources. All year we read the works of Marx and Lenin.” 

A few years later, Stockdale was shot down over North Vietnam and spent the next seven years as a prisoner of war. “In Hanoi, I understood more about Marxist theory than my interrogator did,” he explained. “I was able to say to that interrogator, ‘That’s not what Lenin said; you’re a deviationist.’”

Reading Marx and Lenin didn’t make Stockdale a Marxist. It helped him understand and resist his captors. Interacting with stuff that challenges you or that provokes you either opens your mind or it serves as an inoculation…Both those things are good. That was going to be my message to the Naval Academy, but it’s one everyone needs to remember. 

America has many problems. Reading too many books is not one of them. In fact, I would argue that our problems stem from the exact opposite. We spend too much time online. We watch too much real-time partisan news. We have a poor understanding of history and our founding principles. We read only things that confirm what we already believe.

If you’d like to be part of the solution, you can donate a book by sending one to the Banned Books Library (912 Main St., Bastrop, TX) or through thepaintedporch.com/banned. And if you happen to be in the area, come by, take one home, and read it. Wherever you are, find out what books people are trying to remove and read them. As Stephen King has said, “Don’t spend time waving signs or carrying petitions around the neighborhood. Instead, run, don’t walk, to the nearest nonschool library or to the local bookstore and get whatever it was that they banned. Read whatever they’re trying to keep out of your eyes and your brain, because that’s exactly what you need to know.”

In a time of misinformation and disinformation, that quote might not always be right, but directionally the argument is good. Read whatever they’re trying to keep out of your eyes and your brain. Read dangerously. Read what they’d rather you not see, not know, not think. Wrestle with it. Challenge and disagree with it.

And, above all, learn from it.

August 6, 2026by Ryan Holiday

“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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