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RyanHoliday.net - Meditations on strategy and life
Blog

You’re Gonna Need This Now More Than Ever

I’m giving a talk in Seattle on 12/3 as part of the Daily Stoic Live tour—grab seats and come see me! I’ll also be in San Diego on February 5 and Phoenix on February 27. More dates will be announced soon—sign up here and we’ll let you know when I’m coming to your area.

I do all my research on physical notecards.

I only read physical books.

If I have to read a research paper or an article, I print it out and go through it with a pen.

The book I am working on now is currently laid out on an old school cork bulletin board covered in push pins. 

There are many easier and more efficient ways to do all this, I’m sure. But I do it the more difficult and low-tech way on purpose. 

That being said, I am not a luddite and I don’t think there’s anything admirable or impressive about being one. 

There is something fundamentally foolish about instinctively resisting and rejecting new technology—and I refuse to do it. 

I have spent many hours trying to figure out AI tools and large language models, seeing where they can make me better, where they might help me. 

In some cases, they have. On our family trip to Greece this summer, I had dozens of places I wanted to visit, scattered across the country with no obvious order or itinerary to route between them. I fed them all to ChatGPT and asked for the most efficient driving route. In thirty seconds, it produced what would have been extraordinarily difficult for me to figure out on my own and ultimately, allowed us to get everything into the trip that we wanted. 

I’ve spent many joyous mornings (and long car rides) with my kids getting it to render ridiculous pictures or tell us stories. We’ve used it to make mockups of things we want to build and had it explain obscure historical concepts in language appropriate for a child. 

But in other cases, my use of AI has reassured me of the value of the old techniques, like when I tried to confirm and source a quote about Abraham Lincoln that I had written down on one of my notecards. ChatGPT first told me it wasn’t about Lincoln at all, instead it was Tolstoy speaking of Dickens…and then when I pushed back, it then tried to tell me it was from Hay and Nicolay, two of Lincoln’s secretaries. When I asked what page I could find this on then—my copy in hand—it then told me that the quote didn’t actually exist. Only when I went back through, page by page, an eight-hundred-page prizewinning biography was I able to confirm that my handwritten note card had in fact been correct. Tolstoy was not involved at all (although he has a great line about Lincoln), it was a 19th century journalist who had known Lincoln well—and the quote was easily findable in many old newspaper databases and public domain books 

More recently, for a project I’m currently working on, I wanted to know how many U.S Naval Academy graduates died in World War II. To its credit, ChatGPT showed its work. First it told me that 6% of Naval Academy graduates who served in World War II died. Then it added that between 1940 and 1945, approximately 7,500 people graduated from the Naval Academy. And from those two numbers, it concluded—very confidently—that about 450 graduates must have died. 

Of course, that looks like thinking. It looks like real reasoning. And I could see the math was correct. The problem is that these numbers actually had nothing to do with each other. The 6% figure applies to everyone from the Academy who actually served in the war. The 7,500 figure is how many people graduated during the war years. But that wasn’t the question, was it? I happened to know from something I’d read that around 54 Academy classes served in World War II so using the wartime graduation count to calculate wartime deaths makes no sense. The two numbers are totally unrelated. Also, why are we estimating at all? If the 6% figure exists, that means that the total is a known figure (and of course it is, the Veteran’s Affairs have to know this statistic). 

In any case, my actual solution was much more low tech. I just found a plaque that listed all the names. 

The point is: If I hadn’t already read deeply in these areas—had I not known roughly what I was looking for—I would have been fooled. I might have written that Tolstoy called Dickens the only real giant of history. If I didn’t have my own brain, I might have been persuaded by what seemed like a math equation but was in fact, nonsense. 

This is what people miss about AI. There’s a lot of talk about why we should be worried about AI making us or certain things obsolete. It’s going to make the humanities obsolete. It’s going to make books, artists, knowledge workers, and expertise itself obsolete. 

But the opposite is true! To use these tools well—to not be used by them—you need exactly the things we’re told are becoming obsolete. A broad liberal arts education. Domain expertise. Critical thinking. A feel for what humans actually sound like. The ability to spot when something seems off. 

Just the other day—while this article was in progress, actually—I got an email from someone pitching me some book for The Daily Stoic podcast? The email address was legitimate. The pitch itself was somewhat compelling. But it was riddled with those AI flourishes that no human I know would ever use. An overuse of words like “crucial,” “unlock,” and “harness.” Phrases like “a tapestry of” and “in today’s fast-paced world.” And those green checkmark emojis.

I’ve used AI enough to know that ChatGPT or Gemini wrote this pitch…which meant I could promptly delete it.

We’re entering a world of AI slop. Not just on social media. It’s not just content creators who are sadly outsourcing their writing and ideating and scripting and pitching to these tools. It’s everywhere. Emails from coworkers. Press releases from corporations. Journalists, marketers, politicians, thought leaders—everywhere you look, people are quietly passing off AI’s “writing” and “thinking” as their own. 

So the essential skill of our time isn’t prompt engineering or coding—it’s having a finely tuned bullshit detector. It’s knowing enough about how humans actually think and write to spot bullshit. It’s having read widely enough to recognize when an answer is hollow, even when it’s dressed up in confident prose. It’s understanding your domain well enough to know what questions to ask and, more importantly, which answers to reject.

We need to know how AI works and what kind of answers it spits out so you don’t get manipulated by people who do. 

We need to have read enough Tolstoy to know when a Tolstoy quote doesn’t sound like Tolstoy. 

We need to know enough history to catch when two figures or events are being linked that never overlapped. 

We need to understand basic statistics well enough to spot when two unrelated numbers are being jammed together just to give you an answer. 

This is the kind of work we have to be willing to do…that we have to choose to do. In the new book, Wisdom Takes Work, I quote Seneca, “No man was ever wise by chance.” We must get it ourselves. We cannot delegate it to someone or something else. There is no technology that can do it for you. There is no app. There is no prompt, no shortcut or summary or step-by-step formula. There is no LLM that can spit it out in thirty seconds.

A little while back, I asked Robert Greene what ​he thought about AI. “I think back to when I was 19-years-old and in college,” Robert said. In a class learning to read and translate classical Greek texts, “They gave us a passage of Thucydides, the hardest writer of all to read in ancient Greek. I had this one paragraph I must have spent ten hours trying to translate…That had an incredible impact on me. It developed character, patience, and discipline that helps me even to this day. What if I had ChatGPT, and I put the passage in there, and it gave me the translation right away? The whole thinking process would have been annihilated right there.”

This is why I do all my research on physical notecards. It is not fast, easy, or efficient. And that is the point. Writing things down by hand forces me to engage and struggle with the material for an extended period of time. It forces me to take my time. To go over things again and again. To be immersed. To be focused, patient, and disciplined. To come to understand things deeply. 

The irony of AI, this cutting-edge technology, is that it makes the oldest skills more valuable than ever. Reading. Thinking. Knowing things. Having taste. Understanding context. Detecting lies or nonsense.

The machines are getting better at sounding smart. 

Which means we need to get better at actually becoming smart.

We need the judgment to separate signal from noise.

We need the discernment to know something seems a little off.

We need the curiosity to not be satisfied with first answers. 

We need patience and discipline.

We need wisdom.

Now more than ever.

 

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November 19, 2025by Ryan Holiday
Blog

The Simplest Way To Feel Better In Terrible Times

I’m giving a talk in Seattle on 12/3 as part of the Daily Stoic Live tour—grab seats and come see me! I’ll also be in San Diego on February 5 and Phoenix on February 27. More dates will be announced soon—sign up here and we’ll let you know when I’m coming to your area.

It’s easy to feel disoriented and disillusioned right now.

There’s so much happening in the world, and so much of it feels terrible. There is dysfunction. There is conflict. There is outright lawlessness. There is corruption. There is cruelty.

But there’s a really simple way to feel better. 

I don’t mean turning off the news—though you should definitely do that, as we’ve talked about. I don’t mean taking care of yourself—though that matters too and you should. Go for a run. Meditate. Eat better. Go to therapy. This is all great.

I’m talking about something simpler. Something that works immediately. Something that every wisdom tradition has taught but we keep forgetting:

Do something nice for someone else.

It may seem like a small thing. In fact, it’s everything.

There’s an old story about a boy who comes upon a beach covered in starfish—hundreds, thousands of them washed up on the shore. It’s an appalling, tragic sight. On the verge of tears, he begins throwing them back into the sea, one by one.

“It doesn’t matter,” an adult tells him. “You’ll never even make a dent in this.”

“It matters to this starfish,” the boy says, as he rescues another one.

He’s right. To the person you’re helping, to the person whose burden you are lessening, there is nothing “small” about it. When the Talmud says that he who saves one person saves the world, maybe that’s partly what they meant—you certainly save that person’s whole world.

We get this backwards so often. Despite the expression “all politics is local,” we tend to think big picture before we think little picture. We obsess over grand gestures, complete solutions, systemic change. Meanwhile, there’s suffering right in front of us. A neighbor who needs help. A food bank down the street. A person we could make smile today.

Marcus Aurelius in Meditations talks about a period of his life where he felt like good fortune had abandoned him. And indeed, it certainly looked like it had. There was the Antonine plague, which would kill literally millions of people during his reign. There were wars, floods, and famines. He would bury several of his children. He was betrayed by his most trusted general in what amounted to an attempted coup. He did not meet with “the good fortune he deserved,” one ancient historian noted, “as his whole reign was a series of troubles.”

But instead of throwing himself a pity party, instead of despairing, he rewrote his definition of “good fortune.” It was not getting everything you wanted, he said. No, “true good fortune is what you make for yourself. Good fortune: good character, good intentions, and good actions.

About five years ago, increasingly disgusted by the commercialism of Thanksgiving and Christmas—at least here in the US—I was thinking about just not participating. I hated that every year businesses were expected to offer bigger and bigger sales for Black Friday and Cyber Monday. I hated the clips on the news about people fighting over a deal on a flat screen television. But I decided instead of just writing about it, I would try to do something about it with my own small business. 

So on Black Friday and Cyber Monday, we ran a fundraiser for Feeding America, a nonprofit that works to provide meals to families experiencing hunger, instead. I put in the first $10,000 and we raised another $100,000. The next year we did it again and every year since. Cumulatively, we’ve raised something like $1M or 10,000,000 meals for people in need. 

Did that save the world? Of course not, but it definitely made someone’s world a little better. And you know what else? It made me and my world better too. 

That’s what generosity does, by the way. Yes, it helps the person who receives it but it also changes you into the kind of person who does stuff like that. 

Yes, this world is filled with overwhelming, intractable problems. We face massive “collective action problems,” as the economists call them. Systems that seem too broken to fix. Suffering too vast to address.

And yet.

And yet it falls to each of us to do what we can, where we can, with what we have.

Seneca reminds us that every person we meet is an opportunity for kindness. The elderly neighbor sitting alone on their front porch. The parent in the airport trying to wrangle their toddlers and carry-ons through security. The coworker who seems to be overwhelmed. How are you doing? Do you need anything? Can I help you with that? These opportunities are everywhere, every day. The question is whether we see them. Whether we take them.

Of course, you don’t need to donate to a fundraiser to make a difference. Money isn’t the only currency of generosity. You can give your time. Your energy. Your attention. Your patience. Your kindness.

You can go on hoping or holding your breath until you’re blue in the face, Marcus Aurelius writes in Marcus Aurelius. People are going to keep doing what they do. If you want to feel good, if you want to see good…you’re going to have to do it. 

I’ve been disappointed and appalled at the idea of SNAP benefits being used as political leverage (to almost complete indifference) here in the U.S the last month. So after seeing our local food bank post about the overwhelming demand they were facing, my wife and I walked over and covered a big hole in the budget. In anticipation of everyone moving the announcements of their Black Friday sales up, we thought, hey, let’s move up our food drive too. 

So that’s what we’re doing!

We donated the first $30,000 and I’d love your help in getting to our goal of $300,000—which would provide over 3 million meals for families across the country! (Just head over to dailystoic.com/feeding—every dollar provides 10 meals, even a small donation makes a big difference.) 

The point is: It’s on us.

We don’t control what’s happening globally, but we do control how we act locally. We control who we are. We control what we do. 

If you want to feel better, do better. Do more. 

Give. 

Give enough that it hurts…and see how great you feel. 

Do something nice for someone else.

It makes life better for them.

And I promise—it will make you feel better too.

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November 12, 2025by Ryan Holiday
Blog

I Stopped Caring About Results (And Started Getting Them)

The week after my first book came out in 2012 was rough. 

I mean, it wasn’t actually rough. I was twenty five. My rent was $900 a month for a beautiful two room apartment in the Garden District in New Orleans. I was with the girl I would eventually marry and I’d just put out my first book.

I should have felt like everything was amazing. 

Instead I was in almost debilitating physical and emotional pain…and it was all self-inflicted. 

Traditionally books come out on Tuesdays and first week sales account for all pre-orders plus whatever comes in between launch and that coming Sunday. And then, you don’t find out whether you landed on the New York Times bestseller lists until late in the day on Wednesday. In those days, there was another equally important list—put out by the Wall Street Journal—that was made public sometime on Friday. 

I’d actually had a great sales week—and great media coverage too—but that middle period of the waiting, that was the reason I was in pain. I was torturing myself in anxiety and anticipation (and alternatively dread) about whether I would make it or not. I’ve said before, but with that first book, Trust Me I’m Lying, I was probably 10% proud of what I’d done and 90% waiting for this news to decide whether I had succeeded or failed. Years of my life had gone into it, I was already so blessed—I got to do my dream, publish a book!—and yet it all hung on how a group of faceless gatekeepers decided to evaluate the numbers that week (because, like so many things in life, even objective sales numbers are not actually objective).

In short, I was doing the exact opposite of what the Stoics teach. I had attached my identity, my happiness, my pride to something I did not control. 

So of course I was miserable!

And of course, I was crushed when I didn’t hit the Times list…and only moderately relieved when good news came about WSJ two days later. 

I’ll tell you, I’m not proud of how I acted in that interminable waiting period (according to my wife, I was awful to be around). But I am proud of how far I’ve come since then.

I don’t mean I’m proud that I’ve hit the lists a bunch since then (I have) but…that is no longer something I think much about.

I once read a letter where the great Cheryl Strayed kindly pointed out to a young writer the distinction between writing and publishing. Writing is all the things that are entirely in your control—the work, the hours at the desk, the ideas you wrestle onto the page. Publishing is all the things that are not entirely in your control—acceptance and rejection letters, the size of your advance, the sales numbers, the bestseller lists, the reviews, the invitations, awards, how it lands with readers, whether bookstores stock it, press bookings.

It’s not that the publishing stuff is not important, it’s just that in focusing on them, people often ignore the basic things that precede them—the stuff that it is impossible to succeed without. 

And this is true in all domains. 

Look, from the outside, it probably seems like people like Tom Brady are obsessed with winning. You see them breaking the tablet on the sidelines when the game is going poorly or you hear about how famously competitive they are and this makes sense. Obviously to win that much you have to really care about winning, right? 

What Tom Brady’s actually obsessed with, he has said, is trying “to get a little bit better each day.”

He wanted to improve the accuracy of his throws a little bit. He wanted to get the ball out a little bit faster. He wanted to make his reads a little bit better. He wanted to be a little bit better as a leader. He wanted to recover after games a little bit faster. Because it’s getting a little bit better every day, compounded over a long enough time, that leads to results.

It’s the same distinction as writing vs publishing. Brady’s obsessed with performance—his performance—and that translated into a lot of Super Bowl victories. 

As I’ve locked more into writing and tuned out publishing, more on the parts in my control than the parts outside my control, the funny thing is that my results have gotten better the more I have flipped this ratio.

It’s a strange paradox. That you could get results by not thinking about them? 

I think this is because the fixation on externals, on things outside your control—whether winning a championship, hitting a bestseller list, or making [$$$,$$$$$,$$$$]—carries a hidden cost. It consumes a significant amount of time and energy that would be better spent doing things that actually generate those results. A musician chasing a spot on the charts churns out derivative work, never finding their unique sound. A speaker fixated on the audience’s reaction loses their train of thought. A swimmer who glances over at the competition or up at the finish creates drag and slows down. Have you ever golfed? You know what happens when you pull your head up to follow the ball. 

I’m not saying you shouldn’t strive to accomplish great things or to do and be all that you’re capable of—you definitely should. Obviously external results do matter to a degree. If my books stopped selling, my publisher would stop publishing them. 

I’m just saying you need to make sure you’re running the right race. 

Epictetus quipped that, “You can always win if you only enter competitions where winning is up to you.” The bestseller list? That’s up to the New York Times. Winning a Grammy? That’s up for the Recording Academy. A Nobel Prize? That’s up to the folks in Stockholm. Even competitive goals like being the fastest person in a race or the richest person in the world—these depend on what your competitors do.

What is in your control is showing up, giving maximum effort, following your training, sticking to your principles, pursuing your calling. If that translates to on the field success, great—in fact, it almost always does. If that translates into career recognition, awesome—and again, it usually does.

Many great artists have talked about this—this paradoxical way results tend to be an accidental byproduct, coming to those who don’t directly pursue them. The comedian Mike Myers once said this was his advice for young creators: “Don’t want to be famous…fame is the industrial disease of creativity. It’s a sludgy byproduct of making things.” Bruce Dickinson from Iron Maiden would say in an interview, “I’m not interested in being famous. Fame is the excrement of creativity, it’s the shit that comes out the back end, it’s a by-product of it.” And Viktor Frankl would talk about how “strange and remarkable” it was that Man’s Search For Meaning became such a success because he wrote it not to “build up any reputation on the part of the author.” After the book sold millions of copies, Frankl shared what that taught him: “Don’t aim at success—the more you aim at it and make it a target, the more you are going to miss it. For success, like happiness, cannot be pursued; it must ensue, and it only does so as the unintended side-effect of one’s dedication.”

Perhaps this is what Eugen Herrigel is talking about in Zen in the Art of Archery. The more you’re aiming, the less you’re focused on your form, the more distracted you are, the more tense you are. Your willful will causes you to miss. 

One night just last week, the week after Wisdom Takes Work came out, I was hanging out with my kids when I glanced at the home screen of my phone and could see there was a text from my agent, Steve. I knew what that text was probably about…so I ignored it. 

The next morning, after I got my boys to school and went for a run, I was sitting in the anteroom, going over some letters I am reading for my next book. Remembering that Steve was catching a flight out of the country later that day, I called him back. He told me the good news: Wisdom Takes Work debuted at #2 on the New York Times Bestseller list, and is on pace to be the best selling book in the Four Virtues Series.

“That’s incredible,” I said. “Now, I’m going to get back to work.”

Don’t get me wrong—I’m deeply grateful to the readers who got the book on the bestseller list. It’s crazy and humbling. In fact, to the extent I do think about a book’s success anymore, it’s the readers I think about. They not only give me the satisfaction of knowing the work is having an impact, but they give me the great fortune of being indifferent to things like bestseller lists—their trust and support matters more.

In Perennial Seller, I quote Stefan Zweig, “I had acquired what, to my mind, is the most valuable success a writer can have—a faithful following, a reliable group of readers who looked forward to every new book and bought it, who trusted me, and whose trust I must not disappoint.” 

In that sense, I was pleased to hear the news that Wisdom hit the bestseller list. I took it to mean that I built that following. It also meant, though, that they trusted me and I had to do my best as a writer to live up to that. I didn’t owe anyone or anything to anyone else. There wasn’t anything else to focus on but that work, which is what I meant when I told Steve I was getting back to the pages in front of me. 

Compared to that nervous, anxious, desperate twenty-five year old waiting for good news almost fifteen years ago, I had come a long way. The news hardly changed my opinion about the work I had done…and it didn’t change what I knew about the work I still had to do. 

The idea is that you enjoy the process, the part that’s up to you. 

This sets you up for good results and it also means that when you’re fortunate enough to get them, they are extra as opposed to validation.

As they should be.  

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November 5, 2025by Ryan Holiday
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