By the way you can come see me in Bastrop (today with Matthew McConaughey) and then next week in Nashville…then in Philly and DC in December!

Almost twenty years ago, when I was 19 years old, I found myself sitting across from a person who would teach me more than just about any single person I have ever known.

It was at The Alcove in Los Feliz and the great Robert Greene was talking to another author about all the trouble he was having finding a good research assistant. I had to restrain myself from jumping over the table. This was literally my dream job. It was what I wanted to do with my life.

Fortunately, before I made a fool of myself, Robert asked if I might have any interest in giving it a shot. It didn’t start with anything glamorous. In the days before AI or even decent software, I spent hours transcribing interviews he had done for a book he was writing. I read obscure books. I found articles. I worked on his website. I went to libraries and scanned pages. I went through old archives. I tracked people down.

And in between, I asked questions. I listened. I watched. I absorbed his research and note card system, which I continue to use to this day. I got to see up close what it takes to do great work. Robert was a generous boss and he paid me well, but the real compensation for the job was that I got to have regular conversations with him. And the real luck of my life has been that those conversations continued after my time as his assistant ended (he’s been on the Daily Stoic podcast here, here, here and here). He’s the person I call when I need advice or am struggling with something. He remains one of my favorite writers ever.

So in honor of his new book, The Law of the Sublime—which is incredible and everyone should read right now—I thought I’d share some of the best things I have learned from this incredible man.

– Value learning over money. I told Robert I would work for him for free. “Nobody,” he said firmly, “works for me for free.” In fact, he would often have to nag me to submit my hours. To me, the money was an afterthought. I always considered having access to him, getting to ask him questions, getting to see how a real pro did the job, as my actual compensation. What would he have normally charged someone as a consultant? How many people would have killed to be able to call him or email him about anything?  “Value learning over money,” as Robert writes in Mastery. Always go to what will teach you the most, not what will pay the most. “In the end,” Robert continues, “by valuing learning above all else, you will set the stage for your creative expansion, and the money will soon come to you.”

– Seize the alive time. When I was thinking about leaving my job at American Apparel to be a writer, Robert took me to lunch. It was kind of a full-circle moment from our first meeting. Encouraging me to take the leap in a year or so, he explained there were two types of time in life: Alive time and Dead time. One is when you sit around, when you wait until things happen to you. The other is when you are using that time productively, actively. You’re stuck at the airport–you don’t control that. You decide whether it’s alive time or dead time (you read a book, you take a walk, you call your grandmother). How was I going to use the next year? What would I have to show for it? Don’t just sit on your hands. Decide: This is an opportunity for me. I am using it for my purposes. I will not let this be dead time for me. It was an incredibly productive period of reading and researching and filling boxes of notecards that helped me write The Obstacle is the Way and Ego is the Enemy.

– Be involved. One of the things I’ve always admired about Robert is that he gets involved. When I met him, he was on the board of directors of American Apparel. Over the years, I’ve seen the different politicians, political movements, and causes he’s supported. He uses his powers to contribute, to change the world. He understands how things work, and he puts that understanding to use.

– Never lose your heart. People think Robert is dark and Machiavellian because of what he writes about. But my own political sense of the world was shaped in part by Robert: here is someone who understands the amorality of history and still has a strong social conscience. It’s funny—people assume that because of his books, he must be super conservative. In fact, he’s not. Nothing brings me joy quite like seeing people on Instagram call us both “libtards.”

– Greatness takes time. Robert worked on The Law of the Sublime for the last seven years. He always takes a long time on his books, but I don’t think he wanted this one to take that long. Because of his stroke, he had to do all of the work by hand. But I’ve never once seen him allow anyone to rush him. He always goes at the pace it needs to take. I think about that when I feel behind schedule. It takes what it takes.

– Be useful—and pay attention while you’re doing it. Some of my earliest work for Robert involved transcribing interviews. I would listen, stop the recording, type, go back, listen again. In our recent conversation, we talked about how easily that work can now be automated. But I also told him what those hours had given me. I got to listen to people who would never have agreed to be interviewed by me. I got to hear how Robert asked questions, what he pursued, how he drew things out of people. There was an education inside the assignment. Robert explained that a good apprentice makes a mentor’s life easier. You figure out what they need. You take something off their plate. You develop a skill that complements theirs. That’s how you earn access. What you do with that access is up to you. You can complete the task and collect the money. You can also study how a person you admire thinks and works. The second part is what stays with you long after the assignment is over.

– Develop your intuition. Robert has this incredible ability to sense where to find the story he needs. He’ll be working on a chapter, trying to illustrate a particular idea, and have a hunch that the perfect example is somewhere in a certain book or biography. He hasn’t found it yet. He can’t point you to the passage. But he suspects that if he digs into that book, he’ll find what he’s looking for. And so often, he’s right. I remember asking about it once, and he said, “I’m like a shark,” able to detect the faintest scent of blood across the vast ocean of information. It’s an incredible intuition he’s developed through decades of reading and researching. He knows so much about history, about different eras, about people, about every school of thought, that he has for books and ideas and stories that Fingerspitzengefühl (fingertip feel) he writes about in The 33 Strategies of War—the instinctive sense of where to go that comes from a “deep knowledge of the terrain.”

– Never settle for mediocre.  Robert’s rigor as a reader and researcher was legendary. When I was working with him on The 50th Law, I saw him decide that the book was going in the wrong direction, toss what he had, and start over.  As his research assistant, he would send me off to find stories for his writing. He taught me to hold what I read—and what I brought him—to a very high standard. Finding the perfect quote or story for whatever he was working on wasn’t enough. Where did it come from? What was the context? Was the source itself legitimate? Does it hold up across other sources? Was I settling for the first thing that seemed relevant or confirmed what I wanted? I see too many books these days that skip over all of those questions. They’re filled with lazy writing and research. Quotes clearly pulled from some quote aggregator website. The same handful of familiar stories. Lines attributed to someone without any indication of where they said it—“As Mark Twain said…” Did he? Where? What was the context? Don’t settle for the first thing that sort of fits. Keep digging. For a better source, a stronger example, a more thoroughly verified quote. Set high standards, then do the work to meet them.

– Be patient. In 2009, I wrote an article about stoicism on Tim Ferriss’s website. This was probably my biggest stage as a writer at that point—and then a few months later, a small publisher emailed me to ask if I wanted to turn that article into a book. It was as if everything I had hoped for was coming together. But I wanted to check with Robert first—did he think I should do it? He told me he was happy for me but actually suggested I turn the book offer down. He said that I was still learning and improving as a writer—that my life experiences were accelerating and that the book would be better each day I waited. He was teaching me to be patient. It’s easier to be patient when nothing is happening though. To turn down a life-changing opportunity? That’s the real test. And he was right. If I had taken the deal I had gotten offered in 2009, my entire life would have been different.

– Concentrate your forces. You can’t do a million things well. Robert mostly just writes, and that’s rare these days. Authors are consultants. Authors are starting apps. There are all these other things we can do. For the last seven years, Robert did almost no speaking. He was writing. I think about that example a lot. The reason Robert is as good as he is is that he follows one of his own laws from The 48 Laws of Power: concentrate your forces.

– Don’t outsource the thinking process. A little while back, I asked Robert 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—as I learned from Robert—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.

– Creativity is a lagging indicator. Robert’s definition of creativity is this: “creativity is a function of the previous work you put in.” Creativity is not mysterious or romantic. It’s tedious, Robert says. “If you put a lot of hours into thinking and researching and reading, hour after hour—a very tedious process—creativity will come to you.” All of my books are lagging indicators. They are a culmination of years of work. This is what keeps me moving—knowing that I have to keep filling and refilling the creative well. Knowing that creative output is a lagging indicator of a lot of hours of tedious work. Knowing that if I want to publish more books in the future, the only question is, am I doing the work now?

– Make your way to the inside. Robert’s metaphor for mastery is being on the inside of something. When we start a new sport, when we get our first job, when we approach a field we haven’t yet studied, we are on the outside. But as we put in the work, as we familiarize ourselves with every component, as we develop our intuitive field, we eventually make our way to the inside. This is a metaphor from Robert I think about constantly. I don’t want to be an outsider on anything I do, I want to make my way inside it.

– Focus, focus, focus. If you call Robert in the middle of the day, he won’t answer. Because he’s working. That might seem like a minor accomplishment, but any writer knows how much discipline that takes. You’re sitting there, the words aren’t coming and you’re begging for any excuse to stop. Robert’s discipline is an inspiration for me and I use it as a model. I don’t often meet it, but I try. I remember once I was with Robert when my phone made a noise and I immediately picked it up to check what it was. He compared the way I instinctively reached for it to a “rat in an experiment.” There’s a reason I have turned off all alerts on my phone. I’m still not nearly as indistractable as Robert is, but I’m far better than I would have been without his example.

– Be loyal to the truth. I once asked Robert about what I think is the thread through all his books, something which is also in short supply these days: an unflinching commitment to reality, even when it’s inconvenient. “Whenever I hold a belief, or I’m writing a book,” Robert explained, “I always start with the premise that I’m probably wrong, that I’m actually quite ignorant, that my idea is pretty stupid. And I look at the evidence on the other side and I examine it and I try to convince myself that my initial idea was right. And if it isn’t, then I change it.”

– Separate understanding from endorsing. People often assume the author of The 48 Laws of Power must be a sinister person. But beneath his Machiavellian reputation, there was kindness, patience, decency, generosity, wisdom. One of the lessons I took from this was to separate understanding a behavior from endorsing it. You need to recognize manipulation, vanity, and ambition. You also need to decide how you will behave.

– Take your work seriously…but never yourself. Again, continuing on the idea of understanding vs. endorsing, people think because Robert’s work is very serious that he must be as well. In fact, he’s hilarious. That’s why I loved his interview on Pete Holmes’ podcast. Other people got to see how funny Robert is. My kids love to send Robert Greene books like “Does It Fart?” and “I Need a New Butt” because they know he’ll love them. It reminds me of the contrast between Heraclitus and Democritus. One, understanding the darkness of the world, would cry. The other, understanding the darkness of the world, would laugh. Which would you rather be?

– Get comfortable with contradiction. People will sometimes email me, “Ryan, Marcus Aurelius contradicts himself. Sometimes he says to zoom in and other times he says to zoom out.” Or they’ll point out that Seneca’s writings tell us to be aware of the dangers of the future and also never avoid anxiety and worry.” Or that they are confused because Law 3 in Robert’s The 48 Laws of Power is “conceal your intentions” but Law 6 is “court attention at all cost.” Isn’t that a contradiction? The answer is yes. Yes, the Stoics contradict themselves. Yes, Robert’s laws of power contradict each other. Yes, I contradict myself. Because the world is complicated, ambiguous, paradoxical, and contradictory. Because different situations call for different things. Because everything in life depends on context. As F. Scott Fitzgerald famously wrote, “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.”

– Having a physical practice is essential to the creative life. It was Robert who first got me hooked on swimming in 2007. I had grown up swimming but had drifted toward running. Robert recommended the Los Angeles Athletic Club, and swimming became part of my life again. I learned from his commitment to it, from the value of time when there was no phone, no conversation, no new information to take in. Some days, it turns it off in a very restorative way. Other days, it lets it wander and work on things. I’ve gotten over grudges. I’ve calmed down. I’ve gotten much-needed space. The temptation under pressure is to eliminate these breaks. But the hours at the desk aren’t the only hours that contribute to the work.

– Be generous with credit. It’s funny, Robert talked about “never outshining the master” and “let others do all the work but take all the credit” in The 48 Laws of Power, yet in reality, he’s generous, patient and supportive. No one has helped me more in my career. I’m sure it’s obnoxious for him to be asked about me in interviews but he never gets frustrated. There’s no way I can repay Robert for his kindness and his patience and his generosity. The only thing I can do is pay it forward.

– “It’s all material,” Robert likes to say. Everything that happens in your life can be used for something useful, whether it’s your writing, your relationships, or your new startup. In the introduction to The Law of the Sublime, Robert describes working on the book after his 2018 stroke. His left hand was frozen. He could no longer type as before and would have to essentially write and edit the manuscript by hand. He could no longer take the hikes that had helped him work through his other books. Originally, he had imagined traveling down the Amazon, encountering chimpanzees in Africa, having extraordinary experiences to write about. Now he could barely get out the front door. “Now my small backyard would have to be my Amazon jungle,” he writes. He began looking at the lizards, squirrels, and hummingbirds. His limitations changed the book. He had to find the sublime in the simplest things—and show readers that they could find it without traveling anywhere or undertaking some great adventure. These obstacles become opportunities. If you start asking more often, “How can I use this to my advantage?”—your creative output will not only get better, your life will too.

– Savor this incredibly rare experience we’ve been granted. Near the end of The Law of the Sublime, Robert writes, “You who are reading this are a current member of the Club of the Living. One by one, all around you and all over the world, people are permanently leaving the Club.” When Robert first taught me about alive time, I thought about it mostly as something that gives you urgency and makes you more productive. As I’ve gotten older, I’ve come to understand what it really does is give you the present moment and make you more appreciative. Of the banal, the mundane, the everyday. The soft paw prints on the dusty trunk of a car, the feeling of a pen gliding across a notecard, the sounds of birds, the subtle shifts of light through the windows—this is what Robert means by the sublime. “That we have been granted this incredibly rare conscious experience of our mysterious universe,” he writes, “no matter how briefly, should fill us with continuous awe.” Sit in awe of existence. Let the rareness of this experience wash over you. Be present for it. Savor it—this brief time we get as members of the Club of the Living.

– Memento mori. We almost lost Robert in 2018, when he suffered his stroke. The people we depend on, the people we learn from, the people we assume we’ll always be able to call—you think there will always be another conversation. Another chance to ask that question. Another opportunity to tell them what they’ve meant to you. But none of that is guaranteed. I’m grateful Robert is still here, still writing, still teaching me. I don’t want to take that for granted. It has been one of the great perks of my life to be able to pick up the phone and ask him for advice. But I don’t get an unlimited number of those calls. None of us gets unlimited time with the people who have shaped our lives. Pick up the phone, send the note, make the trip—tell them what they mean to you, while you still can.

A couple of years ago I was giving a talk somewhere. I forget where exactly, but I remember what happened after because I let myself down.

I was pretty tired—it had been a long flight the day before and I was getting over a cold. I walked backstage and said thank you to the organizers and got ready to go.

“Could we take a picture?” they asked.

Of course, I said, thinking it was some kind of informal thing. It turns out they had a backdrop and wanted me to take a picture in front of their logo…and not just one picture but quite a few with quite a few people. Then they asked if I could wait a few minutes because there was someone else they wanted me to meet…and it was quite a few minutes…and then after I talked to them it turned out they also wanted to do a picture. Oh, let’s do a fun one too! And then, the videographer asked me if I could answer some questions for their podcast and record a testimonial. All the while they were also leading me towards a lunch with some of their clients that they were hoping I’d attend.

None of it was a huge imposition by itself, but it’s not stuff I normally agree to. I’m usually pretty good about saying “No” to things I don’t want to do—especially points that are usually, in the speaking world, points of a contract—but I was exhausted and I was alone and they were friendly. So it all kept adding up, along with my discomfort. What had started as a couple little things turned into basically a fleecing, they were using me for marketing materials and it was taking more and more time (all the while my flight was approaching).

In terms of things that have happened to me in my life, this was hardly the worst thing but when I got back to my hotel room to frantically pack and rush the airport, I couldn’t help but think: I could have stopped that at any point. Why didn’t I say something?

I’ve written a lot about the discipline of saying no. About how we have to get comfortable doing it, standing up for ourselves and protecting our time. About the giant “NO!” sign hanging in my office. About how “No” is a complete sentence. About not saying “maybe” when we really mean no. About how everything we say yes to is saying no to something else. About how we have to get comfortable disappointing people.

I know all this. I’ve practiced it. I’ve gotten much better at it. And yet there I was, following someone around, saying yes to thing after thing because I felt too uncomfortable to say no.

What happened?

This is something that the great Angela Duckworth addresses in her wonderful new book, Situated: Find the People and Places That Bring Out Your Best (we had a great conversation about it on the podcast). Yes, grit is important. Yes, discipline is a skill. Yes, we have to be able to do hard things. But we must also understand: behavior is situational. We’re not the same person in every situation. “The laws of physics are inescapable,” Angela told me. “So are the laws of psychology. And one of the laws of psychology is that we are reactive to our situation.”

Someone who is courageous one day, might not be on another. Someone who is hard to discourage in one area of their life, might be a quitter in another. Someone who is patient at work might be short-tempered at home. Someone who is outgoing around one group of people might be introverted around another. Someone who can say no easily in some settings might struggle to say it in others.

Why?

Because it depends!

It depends on what you ate for breakfast. It depends on how much sleep you got. It depends on your identity. It depends on who you’re around. It depends on where you are. It depends on whether it’s been a stressful day. It depends on so much!

That was one of the lessons I learned from that speaking event—the discipline of not putting ourselves in those situations in the first place. My team had not set me up to succeed. I had not set myself up to succeed.

The old ancient command, proclaimed by the Oracle at Delphi, was: “Know thyself.” “One must know oneself,” the philosopher and mathematician Blaise Pascal reminds us. “Even if it does not help in finding truth, at least it helps in running one’s life, and nothing is more proper.”

Knowing when you make good decisions and when you don’t is key. When you can trust yourself and when you can’t. When you need a buffer or a helper, and when you do better on your own. When you can handle the situation and when you need to get out of it.

Captain Arthur MacArthur—the father of Douglas MacArthur—was serving in New Orleans after the Civil War. There, a cotton broker trying to win the use of some army facilities left a large cash bribe in the hotel room of the young officer. MacArthur declined the bribe but afterwards, sent a telegram to Washington. “I request immediate relief from this command,” he told his superiors. “They are getting close to my price.”

What are your strengths? What are your flaws? What is your limit? Where are your buttons? What makes you tick? What is your Achilles’ heel? What tends to happen when you’re tired or hungry? What tends to put you in a bad mood? What tends to distract, rattle, or overwhelm you? “I tell my students,” Toni Morrison explained, “one of the most important things they need to know is when they are their best, creatively. They need to ask themselves, What does the ideal room look like? Is there music? Is there silence? Is there chaos outside or is there serenity outside? What do I need in order to release my imagination?”

“When are you at your best?” is a question we can apply to our working environments, to our routines and habits, to our information diets, to being a parent, a spouse, a boss, an employee, a friend, a teammate, a neighbor, a citizen.

When you are at your worst matters too. Noticing when my wife and I tend to argue or get frustrated with each other has been helpful not just in avoiding those spats but building a day/life around facilitating when we get along best. Noticing that I almost never get good writing done in the afternoons has been helpful too. Noticing that if I don’t work out in the mornings on the weekends, I tend not to be able to find the time to do it at all (or when I do, it’s a miserable slog) has meant that I fiercely protect that time.

You gotta know your weaknesses and make decisions so you can be strong. You gotta know what brings out your worst and arrange things so you can be at your best. You gotta know who you are not trying to be and set yourself to be who you are trying to be.

Behavior is situational. We are situational.

Which is why you gotta know thyself.

You gotta know the conditions that set you up for success.

You gotta know the people and places that bring out your best.

And your worst too.

I feel like every few weeks I am surprised when I pass by the Bastrop County Courthouse on my way to my office at the bookstore.

First, I start seeing the little bunches of campaign signs.

Then I see the white “Early Voting” signs with their big red arrow.

Again?

Seriously, didn’t we just vote?

There was the primary and then the runoffs. Before that, there were some off-cycle ballot measures, city council, mayoral (and I think a runoff for that too?). I’ve lost count of how many there have been!

It can feel like there is an election on a quarterly basis.

And look, if I find it hard to find the time—someone with complete control over my schedule who works a block and a half away—I don’t know how other people do it.

But I always feel a little flutter in my chest when I walk into the basement of the courthouse and vote and see all the people. That’s what I felt two nights ago. I’d just landed after 24 hours of travel from Australia and snuck in to vote a few minutes before they closed for the night. Not just the people but also the volunteers taking the time to make the mechanisms of democracy work.

I might not agree with all these people. They might not agree with me. We might even be cancelling each other out. Still, it’s just a lovely sight.

Voting is the least you can do as a citizen…and at the same time, it means a lot.

A few years back, an election for city council in my little town was decided by two votes.

Two votes!

That’s one couple who stayed home. Or one couple who decided to go to the polls. I read a while ago about a guy named Anton DiSclafani in Alabama who shared a story about voting in a primary where his political beliefs were vastly outnumbered. Yet, despite the odds, his vote became the deciding one. It was literally determined by a single ballot!

This happens way more than you think. Even in presidential elections. Famously, in 2000, the state of Florida which decided who would enter the Oval Office, was decided by 537 votes out of nearly six million cast. In 2008, a U.S. Senate race in Minnesota was decided by 312 votes. In 2020, a congressional race in Iowa was decided by 6 votes. A 2017 state legislative race in Virginia ended in a tie—they eventually had to pull a name out of a bowl to decide who won. The 2016 US presidential election, which saw some 135 million votes, was decided by roughly 77,000 ballots across three states. Michigan, with an adult population of 7.4 million, was swung by just 10,000 voters.

It’s not always so dramatic but considering the very big debates—and hot feelings—about a couple big data centers they want to build out here in rural Texas, I find it interesting that our county commissioner elections are regularly decided by five thousand or so votes…in a county with roughly 100,000 people. Sometimes candidates run unopposed!

People want to have a say in specific issues—they pile into emergency meetings, fill up the comments section on Nextdoor, and pass around petitions—but when they had a chance to have a say just a few months prior, they stayed home.

The single most important practice in Stoic philosophy is differentiating between what we have control over and what we don’t. And the Stoics accepted that a lot is not in our control. We don’t control the weather. We don’t control the economy. We don’t control the traffic. In the political sphere, we don’t control the bottomless greed and grievances of some politicians. We don’t control the bottomless incompetence of others. We don’t control the corruption or the dark money that has flooded politics. We don’t control how much of the population doesn’t bother voting. We don’t control the gerrymandering and voter suppression. We don’t control who ultimately gets elected.

That’s all outside of our control. But the act of casting a ballot is in our control. We control whether or not we engage in the democratic process. And the Stoics are explicit on this point: the philosopher, they said, is obligated to contribute to the polis, and to participate in politics. This is an essential difference between the Epicureans and the Stoics (Seneca said, “Epicurus says: ‘The wise man will not engage in public affairs except in an emergency.’ Zeno says: ‘He will engage in public affairs unless something prevents him.’”)

When I talked to Sebastian Junger on the Daily Stoic podcast not too long ago, he told me he’s often asked how to feel necessary, how to feel like you’re making a difference, in a great big world where any one person’s contribution can seem insignificant. “And it’s actually surprisingly easy,” Junger said. “I always say there are three ways to be a meaningful part of society. None of them are heroic, but if no one does these things, there is no society. First, donate blood. Second, serve jury duty if called upon. And the final one is, vote. You don’t have to vote, but if you don’t vote, you kind of deserve what you get.”

I try to do all those things. I’ve never actually been called to a jury but I give blood every two months or so…and these days it seems like I have to vote that often as well. It can be a little bit of a pain to do either, but it matters. It matters to the person who gets your donation. It matters to you to be the person who gave the donation.

It’s also the grown-up, responsible thing to do.

Don’t boo.

Don’t complain.

Don’t tweet.

Be an adult.

Make the time.

Go read up on the candidates. Check them for the virtues necessary in a leader. Examine their platform for bullshit and demagoguery. Drive over and wait in line. Understand no one will check every box, but pick the one you can best trust with the responsibilities of power and the common good. Accept that your vote, statistically, probably won’t decide things. Be OK with that and do it anyway.

Do your job. Make your contribution to society.

It adds up. It does matter.

Vote.

I’d put in my hours.

482 weeks.

3,379 days.

That’s how long I’d been studying the Stoics when I sat down to write the Daily Stoic. I was 29 years old and I knew enough to write a couple-hundred-page book, one Stoic entry for every day of the year.

But there’s a difference between knowing something and really understanding it. That’s an important Stoic idea: you don’t read the Stoics once or study them at some point in your life. You are always studying them. You are always learning from them. You’re always understanding them in a new way.

That was ten years ago.

1,042 weeks.

7,294 days.

175,056 hours.

I can hardly believe it’s the ten-year anniversary of *The Daily Stoic.* What have the last ten years of Stoicism taught me? In those ten years, I’ve become a parent. We lived through a pandemic. We lived through political unrest. I’ve learned new things. I’ve met new people. I’ve lost people. I’ve been through some stuff, as I’m sure you have too.

I was lucky enough that the publisher let me go back and update the book based on those lessons for the 10th Anniversary Edition. The words from the Stoics haven’t changed—although we did put a bunch of new quotes and entries in the new book—but I have changed. My understanding of them has gotten deeper and better. And that’s what I’d like to talk about: the Stoic ideas I understand very differently now than I did when I wrote The Daily Stoic ten years ago.

Stoicism asks something of you

When I first came to Stoicism—at 19—I came to it like a lot of young people, especially young men, come to it. I was ambitious. I wanted to know what Stoicism could do for me: how it could make me more productive, more resilient, tougher, wiser.

I was drawn to how the Stoics could help me control my emotions, handle adversity, and stay focused. If Stoicism helps you with that, awesome. But you can’t leave it there, because the point of Stoicism isn’t to make you more productive. It’s not to make you richer. The Stoics believed that the purpose of the philosophy was to make you a better person.

Stoicism isn’t just about what it can do for you. It also asks a lot of you.

Looking at the completed first draft of The Daily Stoic, it hit me: Marcus Aurelius talks about the common good something like eighty times in Meditations. That is more than he addresses almost any other topic, including so many of the ones he has become famous for.

So Stoicism has to be about making you more courageous, making you more just. It has to help you become a better parent, a better neighbor, a better citizen—as we quote Marcus saying in the book, a better forgiver of faults, a better friend in tight places.

When I was younger, I was more interested, selfishly, in what Stoicism could do for me. As I’ve gotten older and seen what the book has done for people, I’m more interested in how I can be of service, what Stoicism is asking of me.

With the success of the book, which is about ideas that are not my own, I’ve had to wrestle with this. I even have a card on my wall next to my desk that says, “Are you being a good steward of Stoicism?” Am I living up to my obligations and responsibilities? Am I doing what Stoicism asks of me?

Every obstacle is an opportunity—but to do what?

When I wrote The Obstacle is the Way in my twenties, I took that Stoic idea to mean there’s always some way to turn adversity into advantage. The simplest idea at the center of the book is that there are hidden advantages in every problem, that businesses and teams and people can take seemingly impossible situations and triumph over them.

But what I’ve come to understand in the intervening years is that the Stoics were getting at something more profound than the fact that every downside can be flipped into some kind of advantage or transformed into a success story. The “opportunity” the Stoics saw inside adversity, big and small, was the opportunity to practice virtue.

In the new edition’s October 1st entry, we added a quote from the lesser-known Stoic Arius Didymus, laying out those four Stoic virtues: “There are four primary virtues: practical wisdom, self-discipline, courage and justice.” Marcus called them the “touchstones of goodness”—guiding principles for how to act, who to be, and how to respond in any situation.

And there really is no situation that we can’t use as a way to practice these virtues. Even the hardest, most tragic, most heartbreaking moments of life—a terminal diagnosis, a crippling injury, losing your livelihood, burying a loved one—can be transformed by endurance, by selflessness, by courage, by kindness, by decency.

Have the discipline to say no

When The Daily Stoic came out, I was at an inflection point in my career. Some of my books had done well. Some had done not so well. But they certainly hadn’t blown the doors off.

I was working really hard, taking every opportunity, saying yes to everything. But then the book came out and started to do well, then really well—better than anyone could have imagined. It’s a pretty timeless trajectory: at the beginning of your career, you’ve got to say yes to everything so you can get to a point where you start having to say no to almost everything.

Marcus Aurelius says in Meditations to ask yourself, is this thing essential? Because so much of what we do and say is not essential. That was challenging for me. It wasn’t until the pandemic forced me to say no to everything that I realized the cost of all the things I was saying yes to.

I ended up closing down my marketing company. I said no to a lot of the speaking, traveling, and consulting I was doing. I had to say, Hey, what’s really meaningful to me? What are the things that only I can do? What are the things that, if I didn’t do them, wouldn’t get done?

I have pictures of my kids on my wall—my oldest on the top, my youngest on the bottom—and in between is a sign that just says “No.” It’s a reminder that when I say no, I am saying YES to them.

You want to get to what Seneca defines as euthymia, or tranquility, where you have a sense of your path and you’re not distracted by the paths that crisscross yours. Keeping up with the Joneses—or, in his case, the people who are lost, who are wandering this way or that way.

You want to make sure your discipline is not compulsion. That you have the strength to do the things that actually need to be done, and the discipline to say no to the things you shouldn’t do anymore.

Know what enough is

If you’re ambitious, if you’re driven, you always want more. You always want to sell more books. You always want to do more.

Seneca defines this as a form of poverty. He says poverty is not just having too little. It’s also wanting more.

With the success of my books, I had to remind myself: Hey, what was the goal here originally? To write one book. And then the next goal was, what if I could write about this philosophy that I love? So I wrote one book about Stoic philosophy, and I thought that would be it.

Now I’ve written several. The Daily Stoic became a bestseller that put me in a different tax bracket, that gave me security. It gave me purpose. It gave me a mission. It gave me an audience.

But how quickly we move the goalposts. And how quickly we make our happiness dependent on those moved goalposts. Marcus Aurelius talks about the problem with ambition: it’s so often tied to things outside our control.

It’s funny: the same year that The Daily Stoic came out—and it did sell well—a friend of mine, Mark Manson, put out a book, The Subtle Art of Not Giving a Fck,* that sold probably more in that year than The Daily Stoic has sold in its lifetime.

There will always be people who have sold more, done better, who make your accomplishments seem small in comparison. But if you let that make you feel small, you’re stealing from yourself the reality of the success you’ve had.

Knowing what enough is, what you were actually after, what’s in your control, is important. Because you could succeed beyond your wildest dreams and still be miserable, still feel insecure, still feel inferior. And that’s terribly, terribly sad.

Sometimes success can teach us, if we’re willing to listen, what actually matters, what’s actually up to us, and whether we’ve actually succeeded in what we set out to do.

Wish for things to go the way they have gone

In 2016, if you had asked me how I thought the next ten years would go, or how I wanted them to go, I wouldn’t have guessed any of this. I certainly wouldn’t have asked for a pandemic. I wouldn’t have asked for the market to behave the way it did. I wouldn’t have asked for the political disturbances. I wouldn’t have asked for some of the things that happened to me personally and professionally.

Which is the point. You don’t get a choice. Nobody asked. The world is going to do what it’s going to do. We have to figure out how we respond to it. That is the basis of Stoic philosophy.

Epictetus talks about this most movingly, given the adversity he experienced: the key is to wish for things to go the way they have gone. To see them as uniquely fated and designed for you, because they have set you up to be who you are.

If you asked Marcus Aurelius, did he want his reign to be defined by a plague and famine and flood and war? He would have said, “Of course not.” And yet, this is why we admire Marcus. This is what made Marcus great.

If someone else had been in his place in that moment, the world might have turned out very differently. And perhaps if things had gone the way he wanted, he would have failed that test and been an underwhelming or a disappointing figure.

Seneca says fortune is going to behave exactly as she pleases. We can’t be surprised by this. All we can do is prepare. All we can do is respond well. All we can do is use this as an opportunity to be what we could only be in these circumstances.

We are made to be of service

We quote the Stoics over and over again in The Daily Stoic: we are made for each other. The phrase “common good” appears more than 80 times in Marcus Aurelius’ Meditations. He said that a good life is simply about moving from one unselfish action to another, that our only job is to do good for other people.

As I’ve gotten older, as I’ve had kids, as I’ve built businesses, as I’ve interacted with the millions of people who are into Stoicism, I’ve become much more rooted in that idea. Next to my desk, I have a notecard taped to the wall that says, “Am I being a good steward of Stoicism?”

Am I living up to my obligations and responsibilities? Am I using the success that this philosophy has brought me to introduce more people to the philosophy? Am I making positive contributions to the common good?

That question guides everything I do. How we spend our time and money. The content we make. The decision to stop spending money on advertising. The causes we support. The injustices we speak out about. Not all of these decisions are good for business. Some are not popular. Some make people mad. Some have probably cost us business.

But the filter isn’t if I am making good business decisions. It’s if I am being a good steward of this philosophy that’s given so much to me. If I am being of service. If I am doing good for others.

Find one thing every day

The Daily Stoic, as a page-a-day book, mirrors what Stoicism is supposed to be: a daily practice.

Seneca, in one of his letters to Lucilius, said his goal was to find one thing every day. Just a little thing that makes him better, that makes him smarter, that fortifies him against poverty, that helps him prepare for his ultimate death. The path to wisdom is these little things, little by little.

Zeno said something similar: well-being is realized by small steps, but it’s no small thing.

The Daily Stoic could have been just a collection of the greatest hits of the Stoics. It could have been our favorite selections. It could have been some of the best essays, exploring them at length.

But by being a page a day, one thing every day that you review in the morning or at night—and, of course, people with The Daily Stoic Journal sitting down and writing about these passages, reflecting on them—it mirrors what Stoicism is.

That’s what Marcus Aurelius was doing in Meditations. Digesting one thought, one idea, one lesson every single day. Sometimes the same lesson over a period of time, trying to get better as he goes. That’s what Stoicism is as a practice.

Read and reread

It is a strange experience, now that I’m in my late thirties, to pick up something I wrote ten years ago, when I was in my twenties.

As I went back through The Daily Stoic, I found parts that were mortifying, parts that were cringe, parts that I understand and think about totally differently now.

It was the philosopher Heraclitus who said that we never step in the same river twice. Because we are always changing. It’s equally true that we never read the same book twice—because while the contents don’t change, we do. Our circumstances change. The world changes. That’s why it’s important that we read and reread. I couldn’t have anticipated how much my understanding of the Stoics would evolve as I went along. And I couldn’t have fully understood all that I was missing.

For this anniversary edition, Steve and I revisited every page, adding new translations, new stories, and revised meditations. My understanding of the Stoics has gotten deeper, and I wanted the book to reflect that.

It wasn’t until the middle of the pandemic that I was reading Marcus Aurelius and all these allusions—and, in some cases, direct references—to a plague that he was living through fully landed with me. It wasn’t until I had kids that I was able to understand just what a theme it was for the ancients, in this time of infant mortality: worrying about your kids, about something terrible happening to them, and how they would manage that.

That’s what I wanted to bring to the new anniversary edition: another ten years of reading these ideas, thinking about them, and trying to live by them. Along with Steve Hanselman—my coauthor who translated all of the book’s Stoic quotes—I went through it page by page, asking what could be clarified, improved, or added.

There are some things you can only understand at different points in your life. And so you have to read and reread, read and reread, go back to the ideas over and over and over again. You change and grow with the ideas.

Don’t rush through it

One of the most common themes in the Stoic writings is memento mori. Remember you are mortal. I carry a Memento Mori coin with me. It has a quote from Marcus Aurelius on the back: “You could leave life right now. Let that determine what you do and say and think.”

For the Stoics, meditating on mortality is supposed to be sobering, supposed to wake you up. I found that a little depressing at first. But I’ve come to understand, as I’ve gotten older, that meditating on your mortality doesn’t just give you urgency. It gives you the present moment.

In one of the most haunting passages from the Stoics, Epictetus and Marcus Aurelius both talk about this: as you tuck your children in at night, tell yourself they may not make it until the morning.

Before I had kids, I took it to mean that attachments can be a source of vulnerability. This is like the Zen Buddhist idea: the cup is already broken. Is that what that practice is?

Now, having done hundreds and hundreds and hundreds of bedtimes with my kids, particularly in some scary moments like the early days of the pandemic, I’ve come to understand what they’re saying: Slow down, man. Why are you rushing through this? This could be your last bedtime. Be present for it. Enjoy it. Soak it in. You don’t have anywhere to be. You are where you’re supposed to be in this moment.

On the one hand, memento mori can help you speed things up, give you urgency. But on the other hand, it can help you slow things down. Savor this second. Savor this moment.

At 29, memento mori made me go faster. At 39, it reminds me: don’t rush this. Because what are you rushing towards? You are rushing towards death. You are rushing towards the end of this.

Even in the best-case scenario, your kid’s not going to be four forever, not going to be five forever, not going to live in your house forever. You only get to do this so many times. I only get to make so many videos. I only get to write so many books. I only get to do the dishes, do this drive in traffic, so many times. Don’t rush through it.

You don’t graduate from philosophy

The final lesson is embodied in the original and ten-year anniversary editions of The Daily Stoic. The original was itself the result of many, many drafts. Ten years later, there was still more to revise. Even recording the audiobook for the new edition, I was still making notes and changes.

Stoicism is an evolving thing. Your study and understanding of it is an evolving thing. It is not something you studied. It is something you are studying.

As I said earlier, when The Daily Stoic came out, I’d been studying Stoicism for a decade. Now I’m two decades in. But hopefully my understanding of it will be better three decades in and four decades in and five decades in. When I do a 25-year anniversary edition, I hope there are even more things to change, many new things I’ve learned.

There’s a story about Marcus Aurelius. He’s seen leaving his palace, and a friend asks him, “Where are you going?” And he says, “I’m off to see Sextus the philosopher to learn that which I do not yet know.”

He’s saying that we have to remain a student. Not just a student when we’re young. Even as an old man, even as a philosopher king, he is still learning.

I am still learning about Stoicism, still reading new things, still understanding these things in a new way. You cannot learn that which you think you already know, Epictetus said. If you think you understand it, if you think you’ve got it, if you think you’ve graduated, that is the second it stops for you.

Don’t be a know-it-all. Focus on what you don’t know. Focus on all the things you want to know. Keep learning. Keep growing. Keep coming back to the same ideas and getting new things out of them.

You don’t graduate from philosophy. You practice it. Even if you teach it, you remain a student. Seneca said: “We learn even as we teach.”

I have learned so much talking and writing about Stoicism, writing this new edition, writing the Daily Stoic email for the last ten years, making videos, doing the Daily Stoic podcast. And I still have so much left to learn.

I’m still struggling every single day to apply it all a little bit better to my life.

In the middle of Rome, there stands one of the great trophies of history, the Column of Marcus Aurelius.

The nearly 100-foot monument was put up to commemorate Marcus’ victories during the Marcomannic Wars. It is covered in carvings depicting scenes of his armies marching, crossing rivers, laying siege to cities, fighting battles.

It’s a towering celebration of Marcus’ achievements, literally carved in stone.

But you know what? Marcus didn’t get to bask in all this glory. He died before the column was finished.

And then, in the sixteenth century, Pope Sixtus V had the monument restored and put Saint Paul on top instead. They even added a new inscription at the bottom, attributing all of the victories to the wrong emperor.

I was thinking about all of this a couple months ago, standing beneath the very monument. It was a little over 5 kilometers into what would be the furthest I’ve ever run in my life—50 kilometers (31 miles) through the streets of Rome, stopping at some of the most important Stoic sites in the world along the way.

Why did I run a 50K by myself through the streets of a foreign city during the hottest part of the year—literally the hottest it has ever been in Europe?

Because it’s hard.

And doing hard things is good for you. That was the whole point. Do we do hard things because we want to impress people? Because we want to beat other people? Because we want a medal or a trophy?

No. As Marcus’ victory column is a pretty good reminder, doing things for a trophy is a terrible reason to do things.

That’s why I like doing challenges like this, more than races or competitions. There was no starting gun for this run, no official course, no medal waiting for me at the end. I picked the start time. I picked whether it would start at all…and certainly whether I would finish. I like things where the victory is what I get out of it.

A few kilometers after the column, I got lost. I did a one-mile loop in completely the wrong direction. I was already trying to run farther than I had ever run before and now I’d added an extra mile. But I knew something like this was going to happen. When we do hard things, we have to be prepared for them to be harder than we’re anticipating. If you go into something thinking, This is all the gas I have in the tank. This is all I’m capable of doing. I need everything to go right, you’re in a really vulnerable position. Everything is not going to go right. As Seneca said, the unexpected blow lands heaviest. If I was lost and disoriented and mad at myself right then, this would have been harder than it was.

Instead, I figured out where I screwed up, turned around and kept going. What else are you going to do? From there, I ran up to the Campidoglio and the equestrian statue of Marcus Aurelius, past the Colosseum, through Circus Maximus and eventually out toward the Appian Way.

Almost thirteen miles in, I stopped at what is supposedly Seneca’s tomb. We don’t know for certain. There are no inscriptions identifying it, and two thousand years is a long time and stuff starts to disappear. The last time I had been there was about thirteen years earlier. I had a picture of myself from that trip.

We see ourselves every day, so the passing of time can be invisible to us. Then you come back to a place you haven’t been in a long time. I looked at that old picture of myself. I feel the same. I feel great. I feel better than I did then. But you look at it and you go, Oh, I have more gray hairs now. I have more wrinkles. I can see the last ten years. Marcus Aurelius talks about time being this vicious, unrelenting, ceaseless, almost merciless flow of events, faster and faster and faster, taking us with it.

Standing there at Seneca’s tomb, I wondered if he knew that his plays would still be read two thousand years later. I wondered if he knew that his grave would get worn down by events and eventually forgotten.

By the time I got to the turnaround point, I was 15.64 miles in. I felt pretty good. I was hydrated (Rome is filled with little fountains of fresh drinking water). The shade had been nice. But it was getting hot and I was way behind schedule. It was already 8:40 in the morning, three hours and forty minutes after I’d started.

I hadn’t quite budgeted for how long all the stopping and filming was going to take. Whenever I’m preparing to do something challenging, I like to try to talk to and learn from someone who has done something similar before. Googling around before this run, I found a guy named Luke Tuttle who had run 53 kilometers into Rome and written about it on his blog. So I reached out. I had a million questions for him, and the conversation was so great that we turned it into an episode of the podcast.  He gave me some really good advice: Just let it take however long it takes. You’re not gonna be glad you rushed through it. Take your time. Stop. Admire the sights. Soak it in. If you have to walk, you have to walk.

The point isn’t to win at your hobbies. The point is to do it, to have fun doing it, to experience it, to be there for it. You don’t rush through other things that are pleasurable, and then for some reason, physical activity we try to get done as fast as possible.

It was funny: I wasn’t racing anyone. There wasn’t even a race. Other than trying to beat the full heat of the sun it was impossible to be “behind schedule.” So I took a break, turned around and started running back.

Eventually I got to the point where there were seven miles left. You know you’re doing something hard when you think, only seven miles left. That’s one of the great things about doing hard things. You push yourself, you raise your threshold higher and higher until what used to seem like a lot now only seems like a little.

A few miles later, I’d officially done a marathon. I still had five-ish miles to go. At that point I was thinking about something Epictetus said: Whatever difficulties you face, understand what resources you have inside you. How was I going to get through the last five miles? With the same willpower and strength and training that got me through the first twenty-six.

Honestly, this is my favorite part. They say you’re not really pushing yourself until you get to your limits. It’s after you get tired and keep going that the muscle and strength and fortitude are earned.

It’s a little like working on a book. The first two-thirds, sometimes even the first 80 percent, is the really hard part. You don’t know if you’re going to make it. You don’t know if the thing is going to work. Then you reach a point where you know you’re going to make it as long as you don’t quit. You’ve crossed most of the difficulties off. You have some momentum. You’re in a rhythm.

You have this sense of what you’re capable of because of what you’ve just done. You just gotta see it through.

Somewhere around mile 29.5, I lost it. That was apparently my limit. I was fucking dying at the end. Whatever graceful ideas I had about finishing strong disappeared. I staggered into this little restaurant stand alongside the Tiber and asked if they had water and took Apple Pay. They were incredibly confused about this person stumbling about and slurring his words. I drank two water bottles and then basically  limped the rest of the way.

The whole thing took much longer than I thought. It was much harder than I thought. I got lost. I stopped more than expected. The last couple miles took everything I had.

And then my son popped out from an alleyway and spontaneously joined me, which was just the best. Some thirteen years earlier, somewhere along the Appian Way, I had asked my wife to marry me. And now I was back, finishing this run on that same ancient road with my nine year old son jogging along for the last couple hundred yards.

That’s why we do hard things.

I started the morning knowing I was going to try to run further than I ever had in my life.

Six and a half hours later, I knew a little bit more about myself.

About where my limits are.

About what I’m capable of.

About what I’ve got in the tank.

That was the trophy.

And that one I get to keep.

Before we get into today’s piece…tomorrow I’m hosting a live Q&A session with everyone in the Read to Lead course over at Daily Stoic. Today is the last day to sign up and get your invitation—I hope to see you there! 

Reading is a good thing. 

Every book teaches us something, makes us a little smarter and wiser, right?

And not enough people read enough…

So learning how to read faster is the answer?

No, it’s not. 

Speed reading is not only a scam. It’s missing the point. 

I get this a lot. Because I talk about reading quite a bit, people assume I am a speed reader. I’m not. Across all the other great readers I’ve gotten to know and all the great readers throughout history I’ve studied, I can’t think of anyone who attributed how much they read to how fast they read. I can’t think of a single example of a “speed reader.” 

I just spend a lot of time reading.

Because it’s important. Because I enjoy it. 

I like food. I like music. I don’t rush through those either. Nobody tries to have sex faster, do they? Don’t most people try the opposite?

But here we are with people listening to audiobooks at 2x or 3x speed. Here we are with speed-reading courses that will teach you special techniques to blaze through books. Here we are with rapid-reading apps that flash words at you faster and faster to up your words-per-minute rate. Here we are with people hung up on how many books they read instead of how much they get out of the books they read.

Great readers take their time. Great readers read deliberately. Great readers read actively. I think of people like Joan Didion and Emerson, who filled hundreds of commonplace books with handwritten passages and quotes and ideas from the books they read. People like Montaigne and John Adams, who were lifelong producers of “marginalia,” covering the margins of their books with notes, comments, questions, disagreements, free-form musings, curiosities they wanted to investigate further. People like Major George Patton and Octavia Butler, who were dyslexic and had to struggle just to make sense of the words on the page and still were voracious readers.

People who read a lot of books spend a lot of time reading. There’s no way around this. “The best way to read quickly,” as Tyler Cowen has said, “is to read lots. And lots…Reading quickly is often, in a margin-relevant way, close to not reading much at all.” 

In Wisdom Takes Work, I tell a story about a samurai warrior named Banzo, who sought an education so that he could impress his father. Told by a great teacher that mastery would take ten years, he was aghast.

“I can’t wait that long. What if I work extra hard?”

“OK,” the master said. “Thirty years.”

“But I will do whatever it takes to make it go faster,” Banzo pleaded.

“In that case,” the master said, “it shall take seventy years. A student in a hurry learns the slowest.”

The whole point of reading is that it’s hard, but that the hard is worth it. The whole point of a book is that there is a lot in there and it will take time to get it out. There is a payoff and that payoff is priceless wisdom. In one of the first passages in Meditations, Marcus Aurelius wrote that one of the most important lessons he learned in life was to invest in his education and to always regard “the resulting costs as money well-spent.” 

That seems to be another thing great readers have in common: they regard all the time (and money) spent reading as well-spent. A big part of how I manage to read as much as I do has come down to identifying as a professional reader, and by that I don’t just mean I read as part of my job as a writer or a bookstore owner, but that I see reading as my job.

It makes me a better person. It makes me a better parent. It makes me a better husband. It makes me a better boss. It makes me better at everything I do. So I take it seriously. I invest in it.

That’s the idea behind Read to Lead: A Daily Stoic Reading Challenge—which we are re-launching right now. It was designed for people who want to take their reading more seriously. Not to read faster. Not to sound smarter. Not to impress people with how many books they’ve finished. But to actually get better. To accumulate a mass of true wisdom—that you can turn to and apply in your actual day-to-day life.

There are no shortcuts, no hacks, no way around it. 

To be a great reader, you spend a lot of time doing it—slowly, patiently, attentively, without trying to make it go faster, without being in any hurry.

P.S. If you want to learn to get more out of every book you read, Read to Lead is for you!

It was painstakingly designed to distill everything I’ve learned about being a great reader to help you learn in a few weeks what took me nearly two decades to figure out.

Across 15 challenges (at a pace of one every three days), I’ll walk you through the best of what I’ve learned about reading: how I read, how I choose what to read, how I retain more of what I read, how I work my way through difficult books, and—most importantly—how I take what I read and put it to use in my actual life.

Along with the 15 challenges, you also get access to a private community where you can connect with fellow readers, an instant 20% discount at The Painted Porch Bookshop, and, of course, lots and lots of book recommendations.

Check it out here!

It’s clearly a timeless tendency because Seneca tells us a story about it from two thousand years ago. 

People have always wanted to get something for nothing. They’ve always wanted to get the results without doing the work. 

Especially when it comes to knowledge. 

“Wanting to appear a well-read man,” Seneca writes about a rich but lazy Roman named Calvisius Sabinus, “he thought up the following short cut: he spent an enormous amount of money on slaves,” each one tasked with mastering a different body of work. 

One had to know Homer by heart. Another had to master Hesiod. He had a slave for Sappho, another for Pindar, and one for Simonides—one for each of the ancient Greek poets that an upper-class Roman was supposed to know inside and out.

At dinner parties, Sabinus kept these learned but enslaved Romans at his elbow, ready to feed him quotes, references, and facts to impress his educated friends. And he would insist, Seneca tells us, that summoning knowledge on demand from one’s staff was no different from summoning it from one’s mind. Indulging this notion that any readily available capability was effectively one of your own, a friend suggested Sabinus take up wrestling.

“But I am weak and frail,” Sabinus replied. 

“Don’t say that,” the friend teased. “Consider how many perfectly healthy slaves you have!”

I know it isn’t, but I like to think of this as a parable about AI. It would be nice if someone could do your learning for you, if something could do your thinking for you…but that’s just not how it works. 

Even now. Even as LLMs can do incredible things. 

Because as I’ve said before, the point isn’t to have the information, it is to be the person who has done the work to get the information. You can pay someone to lift something for you…but that won’t make you strong. 

I think about this with my own writing. I am in the middle of working on a biography of someone who wrote thousands of letters, gave hundreds of speeches, sat for oral histories, published his own books and was the subject of countless newspaper reports, classified documents and contemporaneous accounts…and so did the people he was closest to or worked for and with. It would be wonderful if I could just download this into my brain—or I guess my research assistants’ brain—but there is really no way to escape the great Robert Caro’s dictum that you have to “turn every page.”

So my researcher can help me track stuff down, scan stuff, put it in little binders, but ultimately, I have to touch it all. Every damn page. I have to read it all. 

But I don’t mind. I don’t mind because 1) Reading is amazing. I love doing it. Why would I want to skip the best part of my job? 2) Because it is my job, I’m pretty good at it.  

I was lucky in that I had someone teach me how to read well. Marcus Aurelius talked about how “mastery of reading requires a master.” For Marcus, his teacher Rusticus was that master—the one who taught him “to read attentively—not to be satisfied with ‘just getting the gist of it.’” 

For me, Robert Greene was my master. I started as his research assistant, and his rigor as a reader and researcher was legendary. He taught me to go way beyond the “gist.” He taught me to hold what I read—and what I brought him—to a very high standard. Finding the perfect quote or story for whatever he was working on wasn’t enough. Where did it come from? What was the context? Was the source itself legitimate? Does it hold up across other sources? Was I settling for the first thing that seemed relevant or confirmed what I wanted? 

He sent me down rabbit holes. He asked me to go find papers and old works that were, in the days before Google Books, harder to locate. He had me transcribe interviews (something no one does anymore). He introduced me to writers and thinkers I had never heard of. He taught me how he used notecards and how he organized his library. Most of all, he modeled for me what a disciplined, curious and well-read person can be. 

To be a great reader, it’s not enough to read—you have to question, challenge, verify, and mark things up. You have to put books through the wringer and authors on trial. You have to go chase things down, follow footnotes, look up references, look up words you don’t know. You have to have a practice of capturing information and organizing it so it can be drawn on when you need it later.

Sadly, too many people are not taught how to be great readers—and never find the masters who can show them. That’s the idea behind Read to Lead: A Daily Stoic Reading Challenge—which we are re-launching right now. It was painstakingly designed to distill everything I’ve learned about being a great reader—from Robert, from trial and error, from the habits of other great readers I’ve gotten to know, from studying how history’s greatest readers read—to help you learn in a few weeks what took me nearly two decades to figure out.

Read to Lead takes place across 6 weeks at a pace of one challenge every three days (15 challenges and more than 30,000 words of exclusive content), with each challenge built around a specific practice for becoming a better reader. And no, there are no hacks, tricks, or shortcuts. You will not learn how to be a speed reader—that’s a scam. We are not going to show you how to use AI to get out of having to pick up a book. We are not going to tell you to play your audiobooks at 3X speed. We are not going to show you how to shut off that little voice in your head so you can supposedly race through pages faster.

The whole point of reading is that it’s hard, but that the hard is worth it. There is a payoff and that payoff is priceless wisdom. Reading is not about impressing people or winning some game of mental gymnastics. It’s not about winning trophies for your shelf. It’s not about collecting random pieces of information. It’s about accumulating a mass of true wisdom—that you can turn to and apply in your actual day-to-day life.

Valuable things are usually hard-won. Wisdom, a sound and strong mind, is one of them. “The greatest educational fallacy,” James Stockdale would say (himself sent to Stanford as an adult, where he learned to think critically and philosophically), “is that you can get it without stress.” 

No, the road to wisdom is long and rocky.

It’s one beset by obstacles, dead ends, and pits of despair.

One with staggering peaks and terrifying wonders.

One where there is always more ground to cover.

One that, above all, you cannot have anyone—or anything—else travel for you.

P.S. If you’ve never had a Rusticus or a Robert Greene show you how to be a great reader, I tried to build Read to Lead to give you a way to learn from those kinds of masters.

Across 15 challenges (at a pace of one every three days), I’ll walk you through the best of what I’ve learned about reading: how I read, how I choose what to read, how I retain more of what I read, how I work my way through difficult books, and—most importantly—how I take what I read and put it to use in my actual life.

Along with the 15 challenges, you also get access to a private community where you can connect with fellow readers, an instant 20% discount at The Painted Porch Bookshop, and, of course, lots and lots of book recommendations.

And I’ll also be hosting a live Q&A session on September 23 (just sign up by September 22 to get your invitation). It’s one of my favorite things to get the chance to talk about all things books and reading with everyone in the course.

I’d love for you to join us!

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

You did it dude! 

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

It’s the best. 

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

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

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

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

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

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

The 2026 course takes place across 6 weeks at a pace of one challenge every three days (15 challenges and more than 30,000 words of exclusive content). You also receive an instant 20% discount to use at The Painted Porch, access to a private community where you can connect with fellow participants, and, of course, lots and lots of book recommendations.

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

In March 2025, we found two ten-week old puppies dumped on the road near where we live out in the country.

One was white with spots. The other was mostly black with some white on her chest and paws.

Both were emaciated, covered in flea bites, and scared of the thunderstorm that was just starting. 

We took them home and as you can imagine our kids begged for us to keep them. I remembered many years ago reading about “the black dog bias”—that for some reason darker dogs are considered scarier and less likely to be adopted—so we decided to keep that one and found a home, almost immediately for the other. 

It was a good thing because my kids had fallen in love with “Oreo.” 

Like every parent of all time, I was assured that they would take care of her and walk her. And like every kid who has ever made that promise, mine have not exactly followed through.

But I’m not mad, because it means I have to take her for two walks a day (on occasion I succeed in bribing or threatening the boys to come too). Of all the ways Oreo has changed our lives, that’s been the best part. She’s “forced” me to do more of something I love to do. Something I know is really good for me, for anyone.

Walking is good exercise, of course. It burns calories. You get vitamin D from the sun. If the research is correct, apparently getting several thousand steps a day comes with all sorts of benefits for your health and longevity. But I don’t care about any of that. I don’t mind those things, but I walk for the philosophical and psychological benefits.

For centuries, thinkers have walked many miles a day because they had to, because they were bored, because they wanted to escape the putrid cities they lived in, because they wanted to get their blood flowing. In the process they discovered an important side-effect: it cleared their minds and helped them make better work. Literally, the name for the students of Aristotle was the Peripatetics—from the Greek peripatein, “to walk about”—because he did most of his teaching on walks.

Nietzsche’s, Thus Spoke Zarathustra came to him on a long walk. As he would later say: “It is only ideas gained from walking that have any worth.” The choreographer Twyla Tharp talks about going for “mindless mental wanderings” each day. Ernest Hemingway would walk along the Paris quais whenever his writing stalled. Charles Darwin built several walks into his daily schedule. The poet William Wordsworth walked as many as 180,000 miles in his lifetime—an average of six and a half miles a day since he was five years old! 

Even spiritual revelations seem to come on foot. Dorothy Day was a lifelong walker, and it was on her strolls along the beach on Staten Island in the 1920s that she first began to feel a strong sense of God in her life and the first flickerings of the awakening that would put her on a path toward sainthood. It’s probably not a coincidence that Jesus himself was a walker—a traveler—who knew the pleasures and the divineness of putting one foot in front of the other. Indeed, it’s no coincidence that many of the greatest expressions of faith and devotion involve long walks (i.e. pilgrimages) to holy sites around the globe.

The Buddhists speak of “walking meditation,” or kinhin, where movement after long periods of sitting, particularly through beautiful settings, can unlock a different kind of stillness than traditional meditation. In a beautiful letter to his bedridden and depressed sister-in-law, Søren Kierkegaard wrote: “Above all, do not lose your desire to walk. Every day I walk myself into a state of well-being and walk away from every illness; I have walked myself into my best thoughts, and I know of no thought so burdensome that one cannot walk away from it.”

In my life, I’ve been repeatedly gifted with ideas—from the muses, from my own subconscious, I don’t know—on walks. It was on a walk in Bastrop State Park with the kids when I got the idea for The Stoic Virtue Series. I’ve solved business problems and personal problems on walks. My wife can recognize it in my eyes and knows not to say anything when I return from a walk, rushing into the house and heading to the pile of notecards I have on the counter at all times. He’s probably come up with something…don’t interrupt or he’ll lose it and be a mess after. 

I’ll tell you what I’ve almost never thought—except a couple of times in the Texas summer—I have never returned from a walk and regretted it. Walks haven’t solved all my problems, but they rarely make them worse. And even when they haven’t changed anything, they’ve changed my mood—which is usually most of the problem anyway. 

Sitting at our computers, we are overwhelmed with information, with emails, with one thing after another. On a walk, the mind, relieved of all those inputs, can wander, drift, reflect, process, imagine, make connections, have ideas, or simply get a little peace and quiet.

Kierkegaard tells the story of a morning when he was driven from his house in a state of despair and frustration—illness, in his words. After an hour and a half, he was finally at peace and nearly back home when he bumped into a friendly gentleman who chattered on about a number of his problems. Isn’t that how it always seems to go?

No matter. “There was only one thing left for me to do,” Kierkegaard wrote, “instead of going home, to go walking again.”

And so must we.

Walk.

Then walk some more.

Anyway, I’ve got to go now. Oreo is scratching at the door. 

I’ll see if the kids want to come, but either way, I’m walking.

You know, not everything has to be big. 

I realize that the impulse, especially when it comes to business, is to try to grow everything to the absolute biggest it can be.

This is not a new, but it’s certainly a defining trend of our age. After all, all this drama about data centers is being driven by hyperscalers—companies built around taking things that work and scaling them as far as they can possibly go.

But I hate that philosophy…or at least, it’s not what I practice in my life. 

In 2019, I could have started just about any kind of business. A bunch of my friends were starting tech companies. Others had been making a fortune investing, flipping real estate, trading crypto. 

I was the crazy one who decided to open a small bookstore in rural Texas. 

What’s crazier though is that the bookstore worked. And yet do you know what I get asked, probably once a week? “When are you going to open another location?” At least three struggling bookstores have reached out about us acquiring them. 

What strikes me isn’t that people ask—it’s how instinctively they ask. As if expansion were the only logical next step. As if the point of having one successful thing is to have two. Then four. Then forty.

On an episode of The Daily Stoic podcast a little while back, Nate Silver called it “the obsession with scale.” We were talking about how the venture capitalist mindset—where success is defined by scaling 1000x—has seeped into how ordinary people think about their work. About what it means to have a successful podcast. A successful newsletter. A successful creative career. A successful anything.

“In the content space,” Silver said, “VCs tend to analogize content creators or media startups to tech companies. When it’s actually more like running a restaurant. You can run one really nice restaurant. If you’re very lucky, you can even franchise that to a couple of locations and you can write a cookbook and you can get on Iron Chef or whatever. But it doesn’t have to scale beyond that. Unless you want to be a Chipotle or something, which is fine.”

It is fine if you want to be a Chipotle. There’s nothing wrong with building something large if that’s genuinely what you set out to do. But in my experience, most people actually don’t really think at all about what they’re setting out to do. They don’t sit down and consider what success would look like for them, what “enough” would feel like, what winning their particular game would mean. And because they’re not clear on what they actually want, they end up chasing growth indiscriminately. More followers. More subscribers. More platforms. More revenue. More locations. More, more, more—until eventually their thing collapses under its own weight. Or it succeeds and doesn’t fail…but it is an enormous, life-consuming burden. 

“Do Not Go Past The Mark You Aimed For” is one of the most important laws in ​The 48 Laws of Power​. It’s about knowing where you’re trying to go and when you’ve gotten there. It’s about knowing what game you’re playing and when you’ve won. It’s about having the discipline to choose the target and not blow past it. 

I think about this with myself. ​I write books about Stoicism​. If I wrote about something with more mass appeal or if I wrote romance novels or if I ghostwrote celebrity memoirs, maybe I would sell more books, make more money, or be known by more people.

But that wasn’t the mark I was aiming for. If it were, I certainly wouldn’t have chosen an obscure school of ancient philosophy as the means to try to get there.

Or, could The Daily Stoic make more money if we got into t-shirts and hats and supplements and energy drinks and cheap merch? Probably. Could we license the brand to some conglomerate and cash out? I bet we could find a buyer. But if the point of all this was to endlessly raise the ceiling on the amount of money coming in, I would have selected a different line of work a long time ago.

So many people think they have to live a life they don’t want for a long time so that eventually, off in the distant future, they can live a life they do want. They need to make millions or get famous or earn their big break. Then and only then can they…

I’ve always found it’s better to think about what my ideal ordinary day looks like. That, at least, is the mark I am aiming for: for that ideal ordinary day to be most of my days. When an opportunity comes along or I’m faced with a decision, I ask myself: Will this get me closer to that ideal or further away? Will it give me more of the days I actually want to have, or fewer of them?

A really cool job opportunity? I’ll consider it. But wait, it means moving my family to D.C., wearing a suit most days, being on someone else’s schedule—and I won’t be able to write much? Never mind. I could make a lot of money investing in startups? Sounds great. But I’d have to read pitch decks and go to meetings all day? You know what, I’ll pass.

You might ask: “But isn’t this a privileged way to live?” Yes, I do feel very privileged that for me happiness is relatively cheap. My ideal day doesn’t require me to be rich or powerful or important. It just requires that I be good enough at something to sell my services on the open market and strong enough to say no to things that are beyond my needs. That is a privilege, and it’s more accessible than we think. There are plenty of billionaires who don’t have it, plenty of ordinary people who have never lost it.

So it doesn’t take some enormous amount of money. Nor do you have to be famous or well-connected or wildly successful.

It takes discipline. 

The discipline to figure out what you actually want your life to look like.

The discipline to turn down cool, lucrative opportunities. =

The discipline to say no to the investors, the acquirers, the well-meaning people who have ideas for how you can really blow this thing up.

The discipline to not go past the mark you aimed for.

The discipline to not scale.