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.
Source: Ryan Holiday
https://ryanholiday.medium.com/26-rules-to-be-a-better-thinker-in-2026-6393399aad3d
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