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RyanHoliday.net - Meditations on strategy and life
Blog

You Slipped Up. Here’s How To Get Back On Track

It was a long winter. 

You got sick. You lapsed on a resolution. You slipped up. You’re tired, distracted, out of sorts. 

So you’re going to write off the rest of 2026?

That’s crazy.

In one of my favorite passages in Meditations, Marcus Aurelius writes, “When jarred, unavoidably, by circumstances, revert at once to yourself, and don’t lose the rhythm more than you can help.”

I think that word “unavoidably” is key. Slipping up, getting knocked off course, falling off the wagon—it happens. 

And that’s what I want to talk about in today’s email: some rules for a reset. Here—already a couple of months into 2026—is the perfect time. For getting back to first principles, to the things that you said you were going to do, to the person that you know you want to be.

(And by the way, I’m getting together with thousands of Stoics from around the world to do a reset as part of ​The Daily Stoic Spring Forward Challenge​ on March 20. It’s a set of 10 daily, actionable challenges designed to help you clean up your life and spring forward without the weight of bad habits and vices. ​You can learn more and sign up here​. I hope to see you there!)

Focus on what you can control. You’re rattled by what’s going on in the world. The economy. The news. The possibility of AI taking your job. Whatever outrage is dominating the social media feeds this week. In short, you’re spending enormous amounts of time and energy on things you cannot control. Revert to what Epictetus described as our “chief task in life”—getting real clear about what’s up to us and what isn’t. Our actions, our thoughts, our feelings—these are up to us. Other people, the weather, external events, these are not. But here’s the thing: our responses to other people, the weather, external events are in our control. To reset your life, the best place to start is with making this distinction and then choosing to focus on the things that are in your control. If only because it concentrates your resources in the places where they matter.

Wake up early. No one likes getting up early in the winter. Because it’s cold. It’s dark. That’s the famous passage from Meditations: he knows he has to get out of bed, but so desperately wants to remain under the warm covers. “Is this what I was created for?” he asks himself. “To huddle under the blankets and stay warm?” No, it’s not what we were created for. We were made to be up and “doing things and experiencing them.” So we must reclaim the morning hours, the most productive hours in the day. Hemingway would talk about how he’d get up early because early, there was, “no one to disturb you.” Toni Morrison found she was just more confident in the morning, before the day had exacted its toll and the mind was fresh. Like most of us, she realized she was just “not very bright or very witty or very inventive after the sun goes down.” Who can be? After a day of banal conversations, frustrations, mistakes, and exhaustion. If you want to get back on track, if you want to start executing at a higher level, then you have to get in the habit of waking up early.

Protect the best part of your day. Waking up early is critical, but even more so is what we do in those early hours. Waking up early just to get straight into scrolling social media, checking email, watching the news—this is not a reset. You’ve handed the best part of your day to other people’s emergencies, other people’s opinions, other people’s agendas. The novelist Philipp Meyer​ (whose book ​​The Son​​ is an incredible read) told me on the Daily Stoic podcast, “You have to be very careful about to what (and to whom) you’re giving the best part of your day.” Well-intentioned plans fall apart as the day progresses. Our willpower evaporates. The world makes its demands. So it’s key that we prioritize the important things and that we habitualize doing them early. Personally, I fiercely protect my mornings—family first, then writing. My assistant knows not to schedule anything before mid-morning because early calls and meetings don’t just take time—they sap the energy needed for the essential work. I want to give my best self to my most important things. Everything else can come after.

 

Do less, better. Your calendar is filled up. Your inbox is flooded. Your to-do list is overflowing. You’re doing too much. When I talked to the great Matthew McConaughey on the Daily Stoic podcast, he told me the story about a moment a few years ago when he realized he was doing too much. “I had five proverbial campfires on my desk,” he said. He had a production company, a music label, a foundation, his acting career, and his family. “What I did was I got rid of two of the campfires.” He called his lawyer and shut down the production company and the music label. “I was left with the three things that were most important to me. And those three campfires turned into bonfires…I had been making C’s in five things, but when I concentrated on three things, I started making A’s.” A reset requires concentration. It requires elimination, Seneca said: “He who is everywhere is nowhere.” Remember: Everything you say yes to means saying no to something else. And conversely, everything you say no to means saying yes to something else. When you say no, when you cut out the inessential, the Stoics say, it allows you to double down on what is truly essential.

Just make a little progress every day. For a long time, my writing habit was all-or-nothing—either I wrote a lot of words or I didn’t. Over time, I’ve lowered the stakes: now the question is simply, “Did I make a positive contribution to my writing today?” Sometimes that means writing, sometimes editing, adding, deleting. Sometimes I’m home and it’s in my office, sometimes I’m on the road and it’s on a plane or in a hotel room. Sometimes it’s a big contribution, sometimes it’s a little contribution. “Well-being is realized by small steps,” Zeno would say looking back on his life, “but is truly no small thing.” Focus on that—just making a little progress each day. 

Focus on process, not goals. When most people think about resetting their life, they think about setting a goal—lose 20 pounds, read 30 books, write a book. But goals are just finish lines—they’re about achieving something specific, often external, and usually out of your control. A better approach is to focus on the process: the daily work and the practices that will move you forward, regardless of the outcome. As I wrote about recently, I don’t have goals. When I write, I don’t focus on finishing books—that would be overwhelming. Instead, I focus on my notecard system and writing for a couple hours every day. The books emerge from that process naturally, over time. Any time you want to reset things in your life, instead of fixating on specific outcomes, focus on the process that will guide you. The results will take care of themselves.

Make amends. This is actually one of the challenges in the upcoming ​Spring Forward​: to apologize or make amends with someone. Years ago, there was someone I got into a big fight with over one of my books. I eventually emailed them, saying, “Hey, here’s what I’ve been carrying, and I wish I’d done it differently. I feel bad about the consequences for you. I’m sorry.” I’d love to say we became friends afterward, but they didn’t accept my apology—instead, they hurled more anger at me. It was obvious they still carried a lot of resentment, but making amends is also a gift you give yourself. I said what I needed to say, so I’m no longer ruminating or carrying it around. I owned my role in it. I tried to be who I want to be. If they aren’t there yet, that’s okay—I did what I could. As Marcus Aurelius said, the best revenge is not being like the person who wronged you. Maybe they’ll never see your side, but at least you won’t turn into them. We can’t change the past, but we can take responsibility: acknowledge our mistakes, own the pain we caused, learn from it, practice empathy, and try to repair it. This is a kind of deep clean for your life, allowing you to start fresh and move forward without the weight of that emotional clutter.

Discard anxiety. You’re anxious about politics. About flying. About the state of the world. About your kids. The one thing all causes of anxiety have in common? US! The airport is not making you anxious. You are making yourself anxious in the airport! Marcus Aurelius talks about this in ​Meditations​. “Today I escaped from anxiety,” he says. “Or no, I discarded it, because it was within me, in my own perceptions—not outside.” It’s a little frustrating, but it’s also freeing. Because it means you can stop it! You can choose to discard it.

Find a scene. You’re hanging out with the same people you’ve always hung out with. The same circle, the same conversations, the same comfortable group that never quite challenges you or pushes you or expects anything different from you. And then you wonder why you keep ending up in the same place. “Tell me who you consort with,” Goethe said, “and I will tell you who you are.” You need to find a scene that challenges you, inspires you, exposes you to new ideas, holds you accountable, and pushes you beyond your limits. The Spartan lawgiver Lycurgus introduced the common mess hall and required that all citizens eat together. It was harder to eat more than your fair share, more than your healthy share, when you were surrounded by your comrades in battle.

Quit your vices. There’s a story I tell in ​Discipline is Destiny​ about the physicist Richard Feynman feeling a sudden midday pull to have a drink. On the spot, Feynman gave up drinking right then and there. Nothing, he felt, should have that kind of power over him. Ask yourself: What has control over me? Is it caffeine, social media, Netflix, junk food—something more serious? I once heard addiction described as losing the freedom to abstain. Where have you lost the freedom to say no to? And how can you reclaim your power by refusing to feed that habit? If you want a happier, more fulfilling life, decide which vices you’re no longer willing to let rule you.

Do hard things. Making a life change, adopting new habits, doing anything challenging requires courage. As I write about in Courage is Calling: Fortune Favors The Brave, we can’t just hope to be brave when it counts. Courage has to be cultivated. To do the big things that scare you, start with smaller things—start with developing the ability to push yourself to do stuff you’re reluctant to do. To be able to endure the cold reception of a bold idea, start with enduring a cold shower. To be able to step forward when the stakes are high, regularly do that when the stakes are low. To be able to embrace the discomfort of a major life change, accustom yourself to minor discomforts. We treat the body rigorously, Seneca said, so that it may not be disobedient to the mind. We push ourselves in little ways so the big ways stop seeming quite so big, quite so out of character.

Don’t be ashamed to ask for help. Whenever I speak to military groups, I like to share one of my favorite lines from Meditations: “Don’t be ashamed to need help. Like a soldier storming a wall, you have a mission to accomplish. And if you’ve been wounded and you need a comrade to pull you up? So what?” I love how Marcus Aurelius delivers that line—with a shrug. So what? There’s no shame in needing help. Whether it’s therapy, asking for advice, or hiring someone to support you, seeking help is often the key to breakthroughs, growth, and success. Tim Ferriss has a great question that ties into this: What would this look like if it were easy? Often, the answer involves creating support systems or finding the right kind of help. Resetting your life isn’t something you have to do alone.

Get back up when you fall. It’s wonderfully fitting that in both the Zen tradition and the Bible, we have a version of the proverb about falling down seven times and getting up eight. Marcus Aurelius said it was inevitable to be jarred by circumstances, but the key was to get back the rhythm as quickly as possible, to come back to yourself, rather than giving in.

Be kind to yourself. The Stoic philosopher Cleanthes was once walking through the streets of Athens when he came across a man berating himself for some failure. Seeing how upset he was, Cleanthes—normally one to mind his own business—could not help himself but to stop and say kindly, “Remember, you’re not talking to a bad man.” Often, the desire for a reset comes packaged with self-contempt, with some judgment of the version of us who got off track. But this isn’t about beating yourself up. After a lifetime of study of Stoicism, this is how Seneca came to judge his own growth: “What progress have I made?” he wrote. “I have begun to be a friend to myself.” Be kind to yourself. Celebrate your decision to make a change, to get back on track, to make yourself better. That’s what friends do. 

Go the f*ck to sleep. All the other habits and practices listed here become irrelevant if you don’t have the energy and clarity to do them. We have to follow the advice of a book I love to read to my kids: Go the F*ck to Sleep! In the military, they speak of sleep discipline—meaning it’s something you have to be good at, you have to be conscious of, something you can’t let slip. We only have so much energy for our work, for our relationships, for ourselves. A smart person knows this and guards it carefully. A smart person knows that getting their 7-8 hours of sleep every night does not negatively affect their output, it contributes crucially to their best work.

Remember you are going to die. Shakespeare said that every third thought should be of our grave. Perhaps that’s too much. One thought per day is plenty. The point isn’t to be morbid, but to remember that you are mortal. How much time do we waste on things that don’t matter? And why? Because we think we can afford it! Memento Mori. You will die. Live while you can. Live your life as if you have died and come back and all of this is extra. I keep a coin in my pocket to remind me of this and touch it at least once a day. Death doesn’t make life pointless but rather purposeful. And fortunately, we don’t have to nearly die to tap into this.

***

Those are some things I come back to whenever I need a reset.

If you’re ready to take your own efforts to the next level, I’d love for you to join me in the ​Spring Forward Challenge​ from Daily Stoic.

It’s packed with powerful exercises rooted in the best Stoic insights and strategies, and thousands of people around the world will be participating.

Sign up at ​dailystoic.com/spring​—we start on March 20th. I hope to see you there, ready to clear out the clutter and make room for what truly matters.

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March 11, 2026by Ryan Holiday
Blog

Are You Noticing This?

Honestly, it’s been so bad for so long, I didn’t even notice. 

When we moved out to rural Texas in 2015, there was basically no cell phone service at our house or on our dirt road. We tried to fix it at first—I even put a booster on the roof—but it didn’t work. I suppose we could have switched providers…but that seemed like a pain.

We had a landline and wifi-calling, though both were unreliable, especially in storms or when one of our neighbors would cut the AT&T line while grading the road. So we got used to it. We accepted that when we were out and about at home, our phones couldn’t make calls or send texts…for over ten years. It was almost predictable, I’d be back somewhere on my property and some incredibly important call would come through…with just enough service for me to answer and not be able to talk.

That’s why it sort of snuck up on me the last couple months that my phone had full reception when I was out checking on the cows. Or when I was walking the dog. Or even out in the garage. 

An inconvenience that had been part of our lives for so long just suddenly went away. 

And it took me some time to notice it.

Which is something life does, by the way, it gets better and we don’t notice. 

Because we’re so focused on what’s going wrong. Because we’re not paying attention. Because the algorithm and the news cycle is biased. 

I thought the same thing as I was passing through the Austin airport this morning. For the last two years or so, security had been a mess because of a major construction project. As I landed at the American gates and walked to the exit, I noticed that finally the new security entrance was almost done. They were testing it right then. 

The construction had been background noise for so long I had stopped perceiving that, slowly, progress was also happening. And that progress, eventually, inevitably, leads to a completion. 

Having kids is like this too. You are so in the thick of it that you can be blind to the passing of time. Every haircut and nail trim means they’re getting a little older. Same too for every shirt they grow out of. There are obvious benchmarks like walking and potty training and first words but a lot of the other moments are more subtle. You don’t notice the moment you stop lugging a stroller everywhere. There is no one moment when an infant becomes a toddler or a toddler a teenager. These transitions don’t announce themselves.

And you’re also so in the thick of it, dealing with so many problems, that you don’t always notice the ways they’re getting better, like as humans. You don’t notice the night that was the last night they woke you up at 3 a.m. You take for granted the day they started getting into the car themselves and buckling their own seatbelt. You don’t see the way they’re becoming more independent, more competent. It’s not obvious how the things you’re teaching are becoming values and habits, but if you’re doing it right, they are. And it’s easy to miss that everyday this person is becoming a better person, that you are succeeding at this really hard thing. 

I guess what I am saying is that it’s important that we stop and see this. How often do we update our world view to account for what has been fixed, for what’s gotten better, for sources of annoyance that have been eliminated? Or are we carrying around zombie frustrations and anxieties and grievances that we can’t seem to shake?  

Marcus Aurelius—who had every reason to see the world as dark and broken—had this remarkable capacity to notice beauty and progress everywhere. As he was dealing with wars and plagues and betrayals and the loss of loved ones, as his health was failing, he was also writing about the ordinary way that “baking bread splits in places and those cracks, while not intended in the baker’s art, catch our eye and serve to stir our appetite,” or the “charm and allure” of nature’s process, the “stalks of ripe grain bending low, the frowning brow of the lion, the foam dripping from the boar’s mouth.” 

This is someone who cultivated what you might call a poet’s eye—the discipline to notice the beauty in the banal, the mundane, the everyday. He was able to see beauty anywhere…which is really important when you live in ugly times. 

There’s a tendency, especially right now, to look at everything and see only what’s broken. And yes—there’s plenty that’s broken. But it’s worth remembering, stuff has always been broken. Ancient Greece had earthquakes and horrible storms and natural disasters. People suffered. People were killed. People stole the money intended to help those people. Ancient Rome had tyrants and bullies. It had pointless cruelty and systemic injustices. 

It’s always been this way. For centuries, people have fought over minuscule differences. Their governments have been dysfunctional. Their traditions seemed like they were falling apart. Stuff was changing. Stuff was stressful. Stuff sucked. 

It’s not only always been like this…but it’s almost always been worse. You can look out at the news and despair about things. Or you can zoom out and see progress. You can focus on the bad people and miss that the bad people today are almost certainly better than the bad people back then. Even the people you disagree with and dislike politically are not selling their enemies into slavery, sending children to work in the mines and doing science experiments on minorities–things that were not only common in Zeno and Marcus Aurelius’s time, but common enough where you live not that long ago! 

For all the things it is easy to lament about the world, it’s disputable that we live in a time of abundance, medicine, knowledge, and opportunity—things our ancestors could not have imagined in their wildest dreams. If you woke up in a bed this morning, brushed your teeth, flushed your toilet, and had a hot shower, you’re living better than the emperors, kings, and queens of the past. Before indoor plumbing and on-demand heated water, Genghis Khan conquered half the known world but never once felt clean and comfortable the way I do when I dress in sweats after a shower. Before toothpaste, Queen Elizabeth I, one of the most powerful women in history, had teeth blackened by decay. Before refrigeration, Marcus Aurelius, Seneca, Epictetus, Queen Victoria, Cleopatra, Napoleon, Abraham Lincoln, George Washington—none of them ever opened a fridge and cracked open a cold drink on a hot day.

Almost certainly you are living better than you were not that long ago. Think back to your first apartment. Think back that beater of a car you were once perfectly happy with. Think back to what you used to think was a lot of money, what you used to think was ‘fast’ internet. Think back to things you used to hear people saying growing up, think about what things were like for people less privileged than you back then. 

So yes, see what’s broken. Note what needs to be improved. Yes, work to make it happen. But try to notice all that’s been fixed too. Try to see what’s different in your own life. What used to bother you that doesn’t anymore? What was broken that got fixed? What problem solved itself while you weren’t looking?

The world is and always will be messy. But somewhere in the mess, progress is always being made—quietly, steadily, nearly imperceptibly. 

You just have to slow down and notice it.

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March 4, 2026by Ryan Holiday
Blog

26 Rules to Be a Better Thinker in 2026

A couple of years ago, I asked Robert Greene what ​he thought about AI. “I think back to when I was 19-years-old and in college,” Robert said. It was a class where they were  to read and translate classical Greek texts “They gave us a passage of Thucydides, the hardest writer of all to read in ancient Greek,” he explained. “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.”

What does he mean by “thinking process”? He means the slow, tedious, difficult work of figuring something out for yourself. The discipline. The patience. The hours and hours of sitting with frustration and confusion on your way to knowledge and understanding.

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. 

People are talking about what AI is going to replace, that it’s the sum total of all human knowledge, that it’s going to make expertise obsolete. And it’s true it will do a lot and it is unbelievably powerful, but in many ways it makes thinking even more important. You have to be able to interpret what it spits out. You need to know when something’s off. Without domain expertise, without the ability to think critically, to question, to push back, you’ll be fooled. Again and again.

The irony of AI, this cutting-edge technology, is that it makes the humanities more valuable than ever. It makes brainpower even more important. Reading. Knowing things. Having taste. Understanding context. Detecting lies or nonsense. In short: being a discerning, critical, clear thinker.

The tools are only getting more powerful. The noise is only getting louder. We’re being bombarded with more information than any generation in history, and I worry—from some of the emails I get, from the comments I see—that too many people just don’t have the ability to wrap their heads around what’s being thrown at them. Which makes clear thinking one of the most essential skills of our time.

What follows is my advice for what you’re going to need more than ever in this brave new world—26 rules for becoming a better thinker. 

– Take another think. The problem with our thoughts is that they’re often wrong—sometimes preposterously so. Nothing illustrates this quite like what’s called an “eggcorn,” words or expressions we confidently mishear and then contort to match our misperception. “All for not” instead of all for naught. “All intensive purposes” instead of all intents and purposes. But the greatest eggcorn is doubly ironic: people who say “you’ve got another thing coming” are, in fact, proving the point of the actual expression, “you’ve got another think coming.” We need to be able to slow down and use a second think. Especially when we’re sure what we think is right. (And by the way, at least 50% of the time I have to ask ChatGPT to think again because it’s answers are obviously wrong). 

– Take walks. 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 made them better thinkers. Tesla discovered the rotating magnetic field—one of the most important scientific discoveries in modern history—on a walk through a Budapest park in 1882. Hemingway took long walks along the quais in Paris whenever he was stuck and needed to think. Nietzsche—who conceived of Thus Spoke Zarathustra on a long walk—said: “It is only ideas gained from walking that have any worth.” I have never taken a walk without thinking, after, “I am so glad I did that.”

– Embrace contradiction. F. Scott Fitzgerald said, “The test of a first-rate intelligence is the ability to hold two opposing ideas in mind at the same time and still retain the ability to function.” The world is complicated, ambiguous, paradoxical. To make sense of it, you must be able to balance conflicting truths.. F. Scott Fitzgerald said, “The test of a first-rate intelligence is the ability to hold two opposing ideas in mind at the same time and still retain the ability to function.” The world is complicated, ambiguous, paradoxical. To make sense of it, you must be able to balance conflicting truths.

– But don’t confuse complexity with nonsense. Stupid people are especially good at having a bunch of contradictory thoughts in their head at once. So the first-rate mind Fitzgerald described isn’t just about tolerating contradiction—it’s really about the ability to examine and interrogate it. It’s asking, Does this actually make sense? 

– Go to first principles. Aristotle taught that one must go to the origins of things, go all the way to the primary truth of the matter, instead of just accepting common observation or belief. Don’t just blindly accept what everyone else seems to say or believe. Go to first principles. Instead of engaging with an issue from a headline, a tweet, or a take, go to the beginning. Break things down and build them back up. Put every idea to the test, the Stoics said. The good thinker approaches things with a fresh set of eyes and an open mind. 

– Think for yourself. Generally, people just do what other people are doing and want what other people want and think what other people think. This was the insight of the philosopher René Girard, who coined the theory of mimetic desire. He believed that since we don’t know what we want, we end up being drawn—subconsciously or overtly—to what others want. We don’t think for ourselves, we follow tradition or the crowd.

– Don’t be contrarian for contrarian’s sake. Peter Thiel, widely considered a “contrarian,” (and a big fan of Girard) once told me that being a contrarian is actually a bad way to go. You can’t just take what everyone else thinks and put a minus sign in front of it. That’s not thinking for yourself. So in fact, if you find yourself constantly in opposition to everyone and everything (or most consensuses) that’s probably a sign you’re not doing much thinking. You’re just being reactionary. 

– Ask good questions. When Isidor Rabi came home from school each day, his mother didn’t ask about grades or tests. “Izzy,” she would say, “did you ask a good question today?” This doesn’t seem like much, and yet it is everything. After all, questions drive discovery. The habit of asking questions turned Rabi into one of the greatest physicists of his time—a Nobel Prize winner whose work led to the invention of the MRI. Questions are the key not just to knowledge but to success, discovery, and mastery. They’re how we learn and how we get better. And they don’t have to be brilliant, probing, or incisive. They can be simple: “What do you mean?” They can be inquisitive: “How does that work?” They can aim for clarity: “Sorry, I didn’t understand, can you explain it another way?” The point is to stay curious. To never stop asking questions.

– Watch your information diet. When I’m not feeling great physically — tired, irritable, sluggish — usually it’s because I’m eating poorly. In the same way, when I feel mentally scattered and distracted — I know it’s time to focus on cleaning up my information diet. In programming, there’s a saying: “garbage in, garbage out.” Aim to let in the opposite of garbage. Because that leads to the opposite of garbage coming out.

– Go deep. I thought I knew a lot about Lincoln. I’d read biographies, watched documentaries, interviewed scholars, visited the sites. I’d even written about him in my books. So when I sat down to write about him in Part III of Wisdom Takes Work, I thought I was set. I wasn’t even close. So I went deeper. I read Hay and Nicolay. Doris Kearns Goodwin’s 944-page Team of Rivals. Michael Gerhardt’s 496-page book on Lincoln’s mentors. David S. Reynolds’s 1088-page Abe. David Herbert Donald’s 720-page Lincoln. Garry Wills’s Pulitzer Prize-winning book on the Gettysburg Address. I spoke with the documentarian Ken Burns about him, and Doris too. I read Lincoln’s letters and speeches. I went, multiple times while writing the book, to the Lincoln Memorial. In the end, I spent hundreds of hours reading thousands and thousands of pages on the man. Basically, I “dug deeply,” as Lincoln’s law partner once said of Lincoln’s own approach to learning, in order to get to the “nub” of a subject. This is a skill you need. Whether you’re an author, politician, lawyer, entrepreneur, scientist, educator, parent—you have to be able to pursue an idea, a question, a thread of curiosity until you’ve gotten to the nub and wrapped your head completely around it.

– Don’t just read, re-read. A lot of people read, not enough people re-read. Don’t just read books, re-read books. There’s a great line the Stoics loved — that we never step in the same river twice. The books don’t change, but you do.

– Seek out people who disagree with you. In 1961, the Navy sent Commander James Stockdale to Stanford to study Marxist theory. Not criticisms of Marxism—primary sources. Marx. Lenin. The works. His parents had taught him: you can’t compete against something you don’t understand. A few years later, Stockdale was shot down over North Vietnam and spent seven years being tortured in the Hanoi Hilton. His knowledge of Marxism proved essential—he understood the ideology better than his interrogators did. Seneca said we should read dangerous ideas “like a spy in the enemy’s camp.”

– Ego is the enemy. Epictetus reminds us that “it’s impossible to learn that which you think you already know.” The physicist John Wheeler said that “as our island of knowledge grows, so does the shore of our ignorance.” Conceitedness is the primary impediment to wisdom. That’s something I often find with AI, its quickness and confidence in its answers…which are laughably wrong. If you want to stay humble, focus on all that you still don’t know. After all, isn’t that the Socratic method? 

– Beware the Gell-Mann amnesia effect. Named after the Nobel Prize-winning physicist Murray Gell-Mann, the Gell-Mann amnesia effect is the term for a familiar experience: You read an article about something you know well, and you recognize that it’s full of errors, it’s missing context, it’s grossly oversimplifying things. You can’t believe something so bad got published. Then you turn to an article on something you know little about—foreign policy, international affairs, the economy, pop culture—and believe every word. It’s not just that the media exaggerates and sensationalizes. It’s actually worse: Most of the time they don’t even know what they’re talking about. The same goes for AI, which is trained on many of those error-filled sources. I’ve had ChatGPT confidently butcher things I know well. Why would I unquestioningly trust it on things I don’t? The problem is we don’t know what we don’t know. Which means we don’t know when we’re being fooled.

– Be flexible. A colleague of Churchill once observed that Churchill “venerated tradition but ridiculed convention.” The past was important, but it was not a prison. The old ways—what the Romans called the mos maiorum—were important but not to be mistaken as perfect. Plenty of people have been buried in coffins of their own making. Before their time too. Because they couldn’t understand that “the way they’d always done things” wasn’t working anymore. Or that “the way they were raised” wasn’t acceptable anymore. We must cultivate the capacity for change, for flexibility and adaptability. Continuously, constantly.

– Empty the cup. There is an old Zen story about a master who receives a student for tea. As the visitor extends their cup, the master pours…and pours, and pours. The cup begins to overflow. Finally, the student says something: “Stop! The cup is full. It can hold no more.” “Yes,” the master replies. “And your mind is like this cup, full of opinions and speculations. How am I to show you Zen unless you empty your cup?” This is a message about the perils of ego, obviously. It’s a message about keeping an open mind. Because the cup also does not have to be full to cause problems. “If this vessel is not clean,” the Roman poet Horace said in the first century BC, “then whatever you pour in goes sour.”

– Seek understanding, not trivia. Whenever you’re consuming anything, don’t just try to find random pieces of information. What’s the point of that? The point is to understand, to build a foundation of real, true wisdom — that you can turn to and apply in your actual life. On the literary snobs who speculate for hours about whether The Iliad or The Odyssey was written first, or who the real author was (a debate that rages on today), Seneca said, “Far too many good brains have been afflicted by the pointless enthusiasm for useless knowledge.”

– Write to think right. Peter Burke, one of Montaigne’s biographers, believed that Montaigne’s essays were precisely that, a man’s “attempt to catch himself in the act of thinking.” Montaigne said that he wrote as though he was speaking to another person. But that doesn’t mean his essays were casual or off the cuff. Montaigne had to sit and really think—the act of his thoughts flowing from his brain, down his arm, through his pen, and onto the page was a process by which much reflection was transcribed, and, since he continued to edit his writing until the day he died, refined. Only a fool goes with their first thought. A wise person takes time to contemplate.

– Create a second brain—a collection of ideas, quotes, observations, and information gathered over time. As Seneca wrote: “We should hunt out the helpful pieces of teaching and the spirited and noble-minded sayings which are capable of immediate practical application—not far far-fetched or archaic expressions or extravagant metaphors and figures of speech—and learn them so well that words become works.” (Here’s a video on my method).

– Cultivate empathy. Empathy is as much a practical skill as it is a moral one. If you don’t have the ability to think about what other people think about this or that situation, to imagine how something looks from someone else’s perspective, then you have a very limited view of reality.

– Look at the fish. When Samuel Scudder interviewed for a job with the great Harvard biologist Louis Agassiz in 1864, Agassiz placed a dead fish on a tray in front of him. “Look at the fish,” said, and then he left the room. Scudder picked it up, turned it over, counted the scales, and drew it. When Agassiz returned, he was unimpressed. “You have not looked very carefully,” he said. “You haven’t even seen one of the most conspicuous features of the animal, which is as plainly before your eyes as the fish itself; look again, look again!” This went on for three days. “Look, look, look,” Agassiz would say. What did Scudder ultimately discover about the fish? Nothing. It wasn’t about the fish. It was about focus—looking long enough and hard enough to truly see what’s in front of you. This is the skill that good, clear, deep thinking depends on.

– Find your scene. “Tell me who you consort with,” Goethe said, “and I will tell you who you are.” You need to find a scene that challenges you, inspires you, exposes you to new ideas, holds you accountable, and pushes you beyond your limits. Put yourself in rooms where you’re the least knowledgeable person. Observe. Ask questions. That uncomfortable feeling when your assumptions are challenged? Seek it out. Let it humble you.

– Assemble a board of directors. It’s important to have a mentor. It’s important to have a scene. But at the highest levels, we must develop a board of directors—people who advise and consult, who check and even correct you. This isn’t a formality but an essential practice to always be learning and improving. Whose collective experiences are you drawing on? Who in your life can tell you that you’re wrong? That you’re being an idiot? We need other voices around us. We need help. We need to be able to yield. Only a fool declines this priceless resource.

– Beware your inner child. Where do your own emotional patterns get in the way of clear thinking? When you’re hurt or betrayed or unexpectedly challenged, pay attention to how you react. Notice the “age” of that reaction. Is it mature, measured, proportional? Or does it feel more like a wounded eight-year-old lashing out? That’s your inner child—the pain you still carry from early experiences, hijacking your adult mind. Good thinking requires the ability to recognize when your inner child has taken the wheel. This is another benefit of having a board of directors—they can serve as parents to our inner child.

– Keep your identity small. This is a rule from the great Paul Graham. His point was that the more you identify with things—being a member of a certain political party, being seen as smart, being seen as someone who drives a fancy car or someone who belongs to this club or that ideology—the harder it is for you to change your mind or entertain new points of view. Stay a free agent!

– Do the work. In 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.

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February 11, 2026by Ryan Holiday
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