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RyanHoliday.net - Meditations on strategy and life
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!

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September 16, 2026by Ryan Holiday
Blog

This Makes Life Richer, Stranger, And More Interesting (And It’s Basically Free)

Before we get into today’s piece…our Read to Lead course over at Daily Stoic has been updated for 2026! If you want to become a better reader and get more out of your reading, check it out here. Sign up by September 22nd and you’ll also get to join me for a live Q&A—I’d love to see you there! 

It’s been said that books are “uniquely portable magic.” 

But, believe it or not, I think that understates it.

If you love to read, you know what I mean. 

A few weeks ago, I was in Minneapolis and walked by an Indigenous restaurant called Indígena at the Guthrie Theater right next to my hotel. It sounded interesting, so I walked in, ordered, sat down, and pulled out the book I had started on the plane: Death Comes for the Archbishop by Willa Cather.

I’ve found that when you read old famous novels you find one of two things: they are either totally unreadable, or they are so readable you can’t stand it. This book is the latter. It is incredible and sitting there reading it while I ate bison bone marrow was a nearly transcendent experience.

It was like traveling through time and around the world. It starts in Rome with a bunch of cardinals deciding who they are going to assign to the American Southwest to oversee an enormous diocese of tens of thousands of square miles after the Mexican-American War. What follows is a strange book unlike any I’ve read before. It has no huge action scenes, but every page is somehow riveting and beautiful.

It’s got buffalo and corrupt priests. It’s got cathedrals and canyons. It’s got primordial underground rivers and Kit Carson. And the huge sweep of history and territory is breathtaking. Sitting there in Minneapolis in 2026, I was somehow also there inside Cather’s nineteenth-century New Mexico too. 

And when I eventually looked up from the page, the bison bone marrow in front of me, the red neon “YOU ARE ON NATIVE LAND” sign above Indígena’s kitchen, the Mississippi River flowing there across the street, the three-hour flight I had just taken—it all felt a little richer, stranger, more interesting, more meaningful.

It was just one of those fleeting feelings that reminded me of all the reasons I love to read and how reading enriches life in almost unimaginable and inexpressible ways.

In Greece last year, I wandered into a little bookstore in Ithaca that felt more like a small office supply store. There was a book called The Colossus of Maroussi by Henry Miller. I had never heard of it and was momentarily deterred by the horrendously inaccessible title, but I grabbed it anyway. It’s an account of his travels in Greece in 1939. At one point, sailing toward Corfu, he watches the islands come into view.

“Out of the sea,” Miller writes, “as if Homer himself had arranged it for me, the islands bobbed up, lonely, deserted, mysterious in the fading light. I couldn’t ask for more, nor did I want anything more. I had everything a man could desire, and I knew it. I knew too that I might never have it again.”

I got goosebumps. This book I had picked up on a whim, written more than eighty years earlier, perfectly put into words something I was experiencing, there, with my family, walking in the footsteps of all the influences that had shaped my life. I could never have articulated it that way myself but I thought about that passage many times during our trip.

That’s magic. That’s art. That’s humanity. That’s the meaning of life right there. 

That’s what I love about Stefan Zweig’s little biography of Montaigne. I first read it in 2016, then returned to it during the pandemic. Montaigne had lived through plague and religious wars. Zweig was writing about him centuries later, in exile from the Nazis. I was reading them both as my own world was being turned upside down. It’s a very surreal experience to read a book about a man turning inward amidst the cruelty and close-mindedness of his time, written by a man fleeing the brutality and persecutions of his time, and find that both are helping you make sense of yours. 

Three very different lives, separated by centuries, yet here were two men helping me think through questions I was facing myself. How do you think clearly when everyone seems to be losing their minds? How do you remain human in an inhuman time?

And of course, books also let you enter experiences you’ve never had. I heard someone say that a book should be a window and not a mirror—that it should help you look in on someone else, or out into another world rather than back at yourself. That’s why I love memoirs. They help you get inside someone else’s life.

What’s it like to be the most powerful man in the world? Meditations gives us a glimpse. What’s it like to die of terminal cancer? When Breath Becomes Air documents it. What’s it like to be a queer teenage girl with a twin? Tegan and Sara Quin’s book High School is a fascinating picture of it. What’s it like to be an alcoholic in an insane asylum in the 1930s? William Seabrook’s Asylum captures it through the lens of a travel writer who committed himself to one. What was it like to undergo a gender transition in the 1970s? Jan Morris’s Conundrum is an incredible and eye-opening account of it. 

Sometimes you’re not ready for the power of a book, even though it’s there. I thought Cormac McCarthy’s The Road was good when I first read it. It was devastating when I read it after having kids. On the night I finished, all I could do was walk quietly into my son’s room and sob while he slept. The book is one of the most beautiful and profound depictions of struggle and sacrifice and love ever put down on the page. McCarthy had taken me inside another father’s experience, and when I put the book down, I carried it into my own. My son was asleep in his bed. Nothing about that had changed. But standing there looking at him, I felt it differently.

The same book can do that to you more than once. The words stay the same, but your life keeps giving you new ways to understand them.

As part of our Quarterly Classics Book Club, I just reread History of the Peloponnesian War. It was a form of time travel for me. Not just because Thucydides is a great writer who transports you to the three-decade-long war between Athens and Sparta but because I first read this book roughly 20 years ago and I still have my copy. It is crazy to look at notes I wrote at that age…We never step in the same river twice (although I am amazed at how consistently the same passages still strike me). 

But of course, the craziest thing about Thucydides is this sentence from the introduction: “My work is not a piece of writing designed to meet the taste of an immediate public, but was done to last forever.” And here we are, talking about his book 2500 years later. 

You did it dude! 

Of course, these are the big and famous books, the ones I remember where I was when I read them. But just as we quickly forget even some of our most powerful dreams right after we wake up, there have been hundreds and hundreds of other such moments for me in the course of my reading life. Novels that matched up perfectly with a song I was listening to. Nonfiction that taught me the exact lesson I needed at a certain juncture of life. Single sentences that I went back and read five or six times just to savor them. Books that helped me make sense of world events. Writing that was so good I got jealous. An argument I disagreed with so much it prompted me to go write something of my own. 

It’s the best. 

We take it mostly for granted. Think about how many people have lived before you; think of the immensity of their lives, what they said, what they heard, what they did. Think of them sitting at their desk, struggling to articulate this experience for others. Think of the historians and philosophers and wise people who dedicated their whole careers to figuring out how and why certain events unfolded, why and how individuals made fateful decisions. Think of all the books they had read just to create a single, distilled volume they published.

They are all long dead and buried, yet they continue to reach out, collapsing centuries and shattering barriers, traveling across time and space and the vast range of perspectives. They are offering you their hand along your own life path.

It’s magic. It’s so cheap it’s basically free. 

And most people choose not to do it! In any case, most of us don’t do it nearly enough. 

P.S. If you want to experience all the magic of books, it’s not enough just that you read—it’s about HOW you read. It’s about learning how to read more critically, how to digest challenging books, how to find books with the potential of changing your life, how to take what you learn off the page and into your actual life. 

In our all-new 2026 Read to Lead: A Daily Stoic Reading Challenge, you’ll learn how to do that—and much more! Since it first launched in 2019, Read to Lead has been our most popular challenge, taken on by tens of thousands of participants. 

The 2026 course 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). You also receive an instant 20% discount to use at The Painted Porch, access to a private community where you can connect with fellow participants, and, of course, lots and lots of book recommendations.

Additionally, there will be a live video session with me! It’s one of my favorite things to get the chance to interact with everyone in the course—I would love to have you join us!

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September 9, 2026by Ryan Holiday
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.

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September 3, 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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