Wisdom Takes Work by Ryan Holiday

I finished this book in November 2025. I recommend this book 9/10.

Why you should read this book:

This is the fourth book by the author in his Stoic Virtue series. Wisdom Takes Work is about acknowledging that wisdom is about keeping an open mind. It is about slowing down. Throughout the book, people like Elon Musk, Abraham Lincoln, and the French philosopher Michel de Montaigne are mentioned.

Get your copy here.

🚀 The book in three sentences

1. Make your own education. Read-read-read-challenge. Keep filling up those notebooks.

2. Learning is not always a joy. Your mind is not always your friend. Keep pushing for a strong mind and body.

3. Wisdom is slowing. It is helping others. It is being Brave, being Strong, being Good.

📝 My notes and thoughts

• P20. Montaigne, here he is with some new book he's purchased, adding yet another heavy volume to his saddlebags. "Books are," he said, "the best provisions a man can take with him on life's journey."

• P25. While Charles de Gaulle was president of France, he read two to three books a week and was famous for reading all the annual winners of the literary prizes. In the office, German Chancellor Angela Merkel read fifteen-hundred-page history books on the 1800s and took deep dives into Shakespeare. As Secretary of Defense, General James Mattis blocked out an hour each day for "lunch/reading time," having previously managed to read the Stoics and hundreds of other books while actively fighting in a war. Napoleon took 125 books with him during his invasion of Egypt. Franklin Delano Roosevelt managed to read Mein Kampf in German in 1933, shortly after becoming president, in the midst of a ceaseless and overwhelming economic crisis.

• P28. Sadly, too many people are not taught how to read, how to actually extract something usable from the books available to us. Nor are they empowered as readers to quit books that suck, to disagree with a book, or to dive into the rabbit hole of knowledge to master a topic. Because reading is a conversation, great readers are not passive. They put books through the wringer; they put the author on trial. They ask questions. They talk back. And they don't just read occasionally, but constantly, devouring fiction and nonfiction alike, philosophy and history, memoir and biography, poetry and prose. Like Montaigne, whose beloved copy of Lucretius survives with all his notes, Founding Father John Adams was a lifelong producer of what is called "marginalia." The pages of his books show that he was no passive reader, nor was he easily convinced of anything. "Fool! Fool!" he would write. "Nonsense!" But when he liked something, he'd note his agreement, sometimes giving the author a well-earned "Excellent!" In a book on the French Revolution, John Adams wrote something like twelve thousand words of notes and comments. Reading may be a shortcut, but it's still a lot of work. Work that's worth it.

• P44, Returning home from the fields or work at the local inn, Machiavelli removed his mud-spattered clothes and boots before entering his study. Only when he was clean and well-dressed would he be ready to dive into his books. "Fitted out appropriately," he explained, "I step inside the venerable courts of the ancients, where, solicitously received by them, I nourish myself on that food that alone is mine and for which I was born; where I am unashamed to converse with them and to question them about the motives for their actions, and they, out of their human kindness, answer me. And for four hours at a time, I feel no boredom, I forget all my troubles, I do not dread poverty, and I am not terrified by death. I absorb myself into them completely." Again, four hours of uninterrupted focus and study? Yes. Four hours of freedom. Four hours of time travel. Four hours of conversing with the dead.

• P50. Remember the Spartan who was asked if he was stupid because he hadn't said a word at dinner: "A stupid person wouldn't have been able to be silent," he said, and then went back to listing.

• P51. How can you lead if you haven't listened to the people you'll be leading? Why are you trying to solve a problem before you've asked what others have already tried? What information are you crowding out with all your chatter?

• P56. "A collection of anecdotes and maxims is the greatest treasure for a man of the world," Goethe explained, because we can draw on it in conversation and in moments of personal crisis. That little epiphany we had on a hike. That piece of advice we got from our grandmother before she passed. That mistake we made and want to never make again. That fleeting moment of serene happiness and peace. That beautiful passage in the novel we read on vacation. Write it down. Write it down. Trust nothing to memory. Capture it before it passes. Do it in whatever form works best for you.

• P61. This is the key to life: finding the classroom that works for you, that allows you to take over your own education. Because an education is not something you "get," it's something you take. It's something you make. It's there, if we want it badly enough. Leonardo da Vinci was an illegitimate son, which meant he could not attend university in fifteenth-century Italy. So he had to teach himself. The world became his classroom. The philosopher Eric Hoffer did not go to college either. Instead, he spent the Great Depression working in migrant camps and mining towns. He spent twenty-five years as a longshoreman. All the while, he was reading a lot, but mostly his education came from the people he met, and from scraping around on the fringes of society, struggling to survive.

• P64. Epictetus, studying under Musonius, once made a small grammatical mistake on an assignment that he did not think was very important. "It's not like I set fire to the capital," Epictetus said, minimizing the error. It did not go over well. "In this case, the thing you missed is the capital," Musonius told him, following the correction with a stern lecture. Because his student hadn't just messed up—he'd been lazy and then tried to make excuses for it.

• P68. Epictetus would tell his own students, having modeled himself on Musonius, "The philosopher's lecture hall is a hospital. You shouldn't walk out of it feeling pleasure, but pain, for you weren't well when you entered." Valuable things are rarely free. Education is one of them. It's never too late to find a great teacher, but sooner is always better. Because the process will not be a quick one.

• P74. You have to show yourself as somebody with the hunger to learn and excel. You have to show yourself as somebody who listens. Somebody curious. Somebody who is worth teaching. Somebody who is coachable. They give us books to read. They give us problems to solve. They give us riddles to chew on. They provide an example that inspires or even shames ... and sometimes cautions. Even as president, Lyndon Johnson was still the dutiful professional son, looking for guidance from whomever he could get it from. His first move was to ask Kennedy's cabinet members to stay on and to continue to advise him. You will get to lead one day. But first, you must figure out how to obey. First, you must learn how to serve.

• P85. History shows us that change is constant, and for everything that changes, much remains the same. There is always history you do not yet know. Each historical event, each era, is defined by what preceded it, all the way back to the very beginning of time. There is no limit to the number of alleys and parallel tracks that one can go down, a truly infinite number of perspectives to consider for each moment. There is always something new being discovered, an inexhaustible amount of information to take in.

• P95. We put street smarts up against book smarts as if it were some binary code. We must have both. Education and experience are a loop—a mutually reinforcing process. You go to school. You listen to teachers. You read. You try things. You journal. You watch a mentor. You ask a question. You make mistakes. You explore new territory. You study things up close. You get out into the field. You come back to your books. Over and over and over again. Both take work. We do both as part of our work.

• P100. A strong mind needs a strong body and vice versa. In fact, to the Romans, a poorly educated person was someone who hadn't learned to read or swim. You need both the mental and physical. A person is incomplete and unbalanced if they neglect one in favor of the other. Intelligence comes in many forms. A person who can do brilliant things with their mind is wise ... but so is the person who can make their body do incredible things. Is music not a fusion of both physical and cognitive ability? With creativity thrown on top?

• P137. Close-mindedness closes us off. It makes us evil. Our mind, we must understand, is not always our friend. An open window brings in the fresh air and drives out sickness. Stagnant, enclosed water gets dirty, but a fast-moving river is usually much safer to drink from. We must be empty, we must be open, we must keep moving.

• P144. Could you have artificial intelligence do it for you? Or ghostwriter? Maybe—but it would defeat the purpose. We think as we write. Indeed, we cannot finish a sentence until we have carried the thought all the way through. We ponder opposing ideas as we pause between keystrokes, and the pen becomes our third eye. It doesn't even need to be prose—a drawing can help, a diagram lets you see the problem in a new way. On the page, we see the pattern. Transcribing the passage or a quote, we get to feel real genius and insight pass through our mind and our fingers, processing each word, weighing, and understanding the wisdom. We see what we didn't see before. And when we take edits and feedback from others, we see even more, because editing is a kind of interrogation, a process by which we are refining and sharpening our thinking, a way to get our story straight. It doesn't matter if we publish, it doesn't matter what the audience thinks, it was the doing that did the work.

• P151. We need other voices around us. We need help. We need to be able to yield. Only a fool declines this priceless resource.

• P157. We should take learning seriously, but never ourselves. There are enough obstacles already on the path to wisdom. What no one can afford, no matter how brilliant they are, is to get in their own way. To shut their ears or close their eyes out of ego. To repel teachers or eliminate avenues of feedback. To pretend to know something. To become wise in their own eyes ... and thus ... to become no wiser.

• P174. Too much information. Too much bad information. Too much stress. Too much stimulation. Not enough time, not enough nourishment, not enough recovery, not enough care. Not enough stillness. Not enough friendship. Not enough love. You can't just sit around and think all the time. You can't live without sleep or hobbies or joy. Only a fool abuses the only mind they'll ever get. This is the main task: to protect this gift we've been given, to buck the trend and not go crazy as we become more successful.

• P176. Wisdom emerges when we slow down. When we have quiet. When we take care of ourselves. Wisdom is realizing that even if what you do is important ... it's not that important. Wisdom is realizing you are not a prison experiment. You are not a machine. You are an ecosystem. None of it works if some of it doesn't work. Be careful. Take care.

• P191. It's a cliche to complain about how sensitive and weak young people are these days. Maybe they are. But if they are, whose fault is it? They learned it from somewhere ... they say that the truth will set you free, but that's not really true. Truth is heavy. It's uncomfortable. It challenges you, or worse, it obligates you. Once you know how the other half lives, your sense of right and wrong means you may have to do something about it. Once you hear about something you've been screwing up, you have to fix it.

• P196. "The hostile critics are doing me a service," Gandhi once told a friend. "They teach me to examine myself. They afford me an opportunity to see if I am free from the reaction of anger. And when I go to the root of their anger, I find nothing but love." But it takes work to see it this way ... especially when you have a lot of critics. Especially when the criticism doesn't seem loving on the surface.

• P256. Wisdom is not erratic. It is not impulsive or emotional. It is calm. It's cool. It's patient. It's kind. It is philosophical. It's hard to find anyone who had cross words with Lincoln—the man was almost unbelievably agreeable. He did not take things personally. He did not care about people's motives or past mistakes. He only wanted to get the job done. He only wanted to move forward. He showed patience and forbearance, even in the darkest moments of the war.

• P264. He was the four virtues embodied. Brave. Strong. Good. Wise. It's a heavenly combination, yet an attainable one. Lincoln's example sits before us. Perhaps we shall never reach it, but we must never cease to try to approach.

• P274. Lincoln understood that transformation not only took time, but that he had to wait for the right opportunities and could not simply will them into existence. Life had taught him that. Have you learned that lesson? It is so easy for knowledge to puff us up; it is so easy for success to make us stupid. Fools are rarely humble, but brilliant people often are. It's not that you're always wrong, but understand that you always could be. It's the irony of wisdom that the smarter you get, the less you need to feel like a smart person. The less you need to be right. The more comfortable you are with uncertainty and ambiguity, and, of course, humility. Experience should reduce ego, not enlarge it. Study should make us less certain, not more so. That was the power of Montaigne's question: Que sais-je? What do I know? The answer was usually, in fact, almost always: Not much! But by embracing humility, we learn. Because if we know little, it means there is a lot to learn. Curiosity is an open window. Certainty is a closed door.

• P285. Wisdom cares about progress, not itself. Each of us is only a vessel—and not a permanent one. It is inevitable that we will all be replaced eventually. Knowledge is power, as they say, but like the power given to Antoninus, it has strings attached. We owe something to our teachers. We owe something to someone else now, too, to future generations. That debt, as Stockdale described it, is teachership. But we are wrong to see this simply as charity, as some onerous moral obligation—we get something out of it. "The process is mutual," Seneca said of mentorship, "for men learn as they teach." In helping others, we are forced to examine our own thinking, to reflect on our experiences. We sit down and write, putting what was previously intuition into knowledge. And in writing this for someone else, we practice empathy and understanding.

• P288. Art, leadership, and enlightenment demand the ability to handle ambiguity. They require a strong tolerance for contradiction. You have to be able to deal with the mystery and the mist. Because they never go away.

• P296. Even philosophers can be guilty of hypocrisy. Diogenes the Cynic thought Plato was pompous. Invited to a dinner party, Diogenes deliberately tracked dirt in on his shoes, saying that he was stomping on "the vanity of Plato" by soiling his carpets. But Plato, calmer and wiser at least in this instance, could see what was behind Diogenes's scorn for others, something that Diogenes himself so often missed. "How much pride you expose to view," Plato said as he watched this childish performance, "by seeming not to be proud." We'd rather stare directly at the sun than in the mirror ...

• P297. This is why Joan Didion was so reluctant to reduce her notebooks to just a professional tool. Even though she benefited immensely from her compulsion to write and record as an author, she came to see that there was something more profound about these pages she filled on so many mornings, afternoons, and late evenings. Flipping through scraps of dialogue she had put down at the train station in Delaware, or recounting childhood experiences or facts about pollution in New York City, she wondered why she had bothered to write this all down. Was she ever going to use it? Was it important? Who was this person who had felt the need to record so many seemingly banal details? Then she realized that was the point. "I think we are well advised to keep on nodding terms with the people we used to be," she later observed. "We forget all too soon the things we thought we could never forget."