10 Stoic Lessons It Took Ryan 10 Years to Understand

Ten years after publishingThe Daily Stoic https://store.dailystoic.com/pages/the-daily-stoic-10, Ryan shares what he’s learned, what he missed, and what he sees differently now. Thenew 10th Anniversary Edition of https://store.dailystoic.com/pages/the-daily-stoic-10The Daily Stoic https://store.dailystoic.com/pages/the-daily-stoic-10https://store.dailystoic.com/pages/the-daily-stoic-10is out NOW! 👉 Grabhttps://store.dailystoic.com/pages/the-daily-stoic-10your copy here: https://store.dailystoic.com/pages/the-daily-stoic-10 🎟️https://www.dailystoiclive.com/DAILY STOIC LIVE https://www.dailystoiclive.com/| Ryan Holiday is coming to a city near you https://www.dailystoiclive.com/! Grab tickets here https://www.dailystoiclive.com/ | https://www.dailystoiclive.com/ 🎙️AD-FREE https://dailystoic.supercast.com/| Support the podcast and go deeper into Stoicism by subscribing toThe Daily Stoic Premium https://dailystoic.supercast.com/ - unlock ad-free listening, early access, and bonus content:https://dailystoic.supercast.com/ ✉️ FREE STOIC WISDOM https://dailystoic.com/dailyemail | Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email athttps://dailystoic.com/dailyemail -- Stop online threats before they become real-world attacks. Visit ironwall.com/DAILYSTOIC and request a free Risk Assessment to see exactly how exposed your executives are. Hosted on Acast. See acast.com/privacy https://acast.com/privacy for more information.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Ryan Holiday?

  We were looking to spruce up our, our front porch. The weather's finally getting better. We wanted to spend some time hanging out outside with the kids. So we got these awesome hammocks and we actually got them from today's sponsor, Wayfair. If you drove by our, our house, you'd see us out there with our kids reading. We've got this new kitten all hanging out in the hammocks. It's been awesome. And that's because on Wayfair, you'll find quality materials that stand up to real life. They sell furniture and decor that's built to last. And when you shop with Wayfair Verified, it's your shortcut to durable pieces that are hand vetted by product specialists using their 10-point quality inspection. They've got thousands of products at every style and budget, whether you're simply replacing an appliance or transforming your home from top to bottom this holiday season. Wayfair's got great

• 0:43Ryan Holiday?

  reviews as well. So you can find more than 20 million verified five-star reviews from real shoppers. Find pieces made for real life and get even more value with Wayfair Rewards. Join Wayfair Rewards today and get 5% back on every purchase. Head over to wayfair.com to shop all things home, W A Y F A I R dot com.

• 1:07Ryan Holiday?

  10 years ago, I published this book, The Daily Stoic. I was 29 years old and I had been studying the Stoics for over a decade. I'd already written The Obstacle is the Way and Ego is the Enemy. I knew enough about philosophy that I could write a couple hundred page book about it, one Stoic entry for every day of the year. But there's a difference between knowing something and really understanding it. So here we are on the 10-year anniversary of The Daily Stoic. There's a new addition. And I was thinking about some things that I have learned since The Daily Stoic came out. What has the last 10 years of Stoicism taught me? Because in those 10 years, I've become a parent. We lived through a pandemic.

• 1:48Ryan Holiday?

  We lived through political unrest, 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. The words from the Stoics haven't changed, although we did put a bunch of new quotes and entries in the book. But I have changed. My understanding of them has changed. It's gotten deeper and better. And that's what we're going to talk about in today's episode. So you can pick up where I leave off.

• 2:18Ryan Holiday?

  I think when I first came to Stoicism, I came to it like a lot of young people, especially young men come to it today, right? I was young. I was ambitious. I, I wanted to know what, what Stoicism could do for me, how it could make me more productive, how it could make me more resilient, how it could make me tougher, how it could make me wiser. And, and the Stoics have so much to teach us in this regard, right? I, I was drawn to how the Stoics could help me control my emotions, how it could help me handle adversity, how it could help me stay focused. And, and Stoicism is really good at answering those questions. If Stoicism helps you with that, awesome. But you can't leave it there. Because the

• 3:01Ryan Holiday?

  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. It wasn't until we were sitting down and looking at the completed first draft of The Daily Stoic that, that it hit me that Marcus Rios talks about the idea of the common good something like 80 times in meditations, right? 80 times is a lot. 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, has to help you become

• 3:45Ryan Holiday?

  a better parent, a, 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. And as I've gotten older, as I, as I've reflected on the book, as I've seen what it has done for people, I'm more interested in that, how I can be of service, what I can do, what Stoicism is asking of me. With the success of the book, which is about ideas that, that are not my own, I've had to wrestle with this. I even have a, a card on my wall next to my desk. It says, "Are you being a good steward of Stoicism?" Meaning, am I living up to the obligations and responsibilities I have? Am I doing what Stoicism asks of me?

• 4:35Ryan Holiday?

  Obviously, I, I wrote an entire book around this idea from the Stoics that every obstacle is an opportunity. But an opportunity to do what? I think when, when people hear that phrase, certainly when I heard that phrase for the first time, I interpreted it in, how do you bounce back? How do you use this as a chance to grow? How do you use this as a chance to be more successful? Something bad happens, how do you, how do you turn that into something that's good for you? You get fired, how do you, how do you use that as a chance to start your own business, right? Someone rejects you and you use that as motivation to, to prove them wrong. Somebody beats you and you use that as motivation to come back bigger and better next season. Again, great. You, you turn adversity to advantage. But one of the things I've come to understand with the passage of time is

• 5:18Ryan Holiday?

  that, that the Stoics meant this on a, on a deeper, a more profound, a more philosophical level. When Marcus Rios talks about this specifically, he says, "Use this thing as an opportunity to practice other virtues," right? He's not saying that every obstacle and every difficulty is a chance to, to, to be more successful. He's saying it is a chance for you to be the person that you're meant to be. That might be painful, might be unpleasant, might be really, really hard, but it's an opportunity for you to grow as a human being, right? Somebody treats you badly. Yeah, you can use that as motivation or you can use that as a chance to practice patience and forgiveness. Your business failed. Yeah, maybe that's a chance for you to bounce back even better. It's also a chance to practice

• 6:02Ryan Holiday?

  acceptance and humility. So when we're talking about opportunities, we don't just mean professional opportunities. We mean chances to grow, to learn, to be kinder and wiser, to be a better human being generally. That's in a way, a much more elastic formula, but it's also a more profound and meaningful formula.

• 6:30Ryan Holiday?

  When The Daily Stoic came out, I was sort of at an inflection point in my career. It was, it was early enough. Some of my books had come out and done well. Some of them had done not so well, but, but they certainly hadn't blown the doors off by any means. I was working really hard. I was taking every chance. I didn't know that The Daily Stoic could work. I actually trusted my agent, Steve Hanselman, who I wrote the book with, when he said, "Hey, I, I think this is worth taking a shot on." I was willing to take a lot of shots on goal at that point in my life. But then the book came out and it started to do well. And then it started to do really well. And then it started to do even better, like better than anyone could have imagined. And this is a, this is a pretty timeless trajectory, right? At the, 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.

• 7:12Ryan Holiday?

  Marcus Rios mentions this in Meditations. He says, you know, "Ask yourself, is this thing essential?" Because so much of what we do and say is not essential. And the ability to say no, to eliminate the inessential, Marcus is saying, gives you the double benefit of doing the essential things better. And that was a really challenging thing for me. It wasn't until, in some ways, the pandemic forced me to say no to everything, that I really realized the costs of all the things that I was saying yes to. And I had to commit to this Stoicism thing, this philosophy thing. I ended up closing down my marketing company. I said no to a lot of the speaking I was doing, a lot of the traveling I was doing, a lot of the consulting I was doing. And I had to say, "Hey, what's really moving the needle for me? What's really meaningful to me? What is the thing that only I could do? What are the things that if I didn't do, wouldn't get done?" And I don't just

• 7:57Ryan Holiday?

  mean this professionally. I also mean as a person, right? We're so willing to say yes because this cool inbound opportunity comes. But who are we saying no to? What are we saying no to? I have on my wall, a picture of my kids, 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, that discipline isn't just saying yes. It's not just working harder, but it's also having the discipline to say no, to not do the things that you shouldn't be doing. To get to the place that Seneca defines as euphemia or tranquility, he says, where you, you have a sense of what your path is and you're not distracted, he says, by the paths that crisscross yours, right? The keeping up with the Joneses, or in, in his case, he says, "The people who are lost, who are wandering this way or that way." You want to make sure that

• 8:41Ryan Holiday?

  your discipline is not compulsion, that you have the strength to say no, to do the things that actually need to be done, and the strength and discipline to not do the things that you shouldn't do anymore.

• 8:54Ryan Holiday?

  And this connects to another thing, especially to those who are ambitious, who are driven, which is you always want more. And Seneca defines this, though, as a form of poverty. He says, "Poverty is not just having too little, it's also wanting more." And with the success of this book and the success of my other books, I had to remind myself, "Hey, what was the goal here originally?" The goal originally was to write one book. And then the next goal was, "Oh, what if, 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. And then here I am, I've written several. I, I wrote this book that became a bestseller that put me in a different tax bracket, that gave me security, gave me purpose, gave me a mission, that gave me an audience. But how quickly we move the goalposts and how

• 9:36Ryan Holiday?

  quickly we make our happiness dependent on those moved goalposts. Marcus Rios talks about ambition. The problem with ambition is that it's so often tied to things that are outside of our control. And it's funny though, the same year that, that The Daily Stoic came out, and, and it did sell well, a friend of mine, Mark Manson, put out a book, The Subtle Art of Not Giving a Fuck, that sold probably more in that year than this book has sold in its lifetime. There's always going to be people that have sold more than you, that have done better than you, that make your accomplishments seem very small in comparison. But if you let that make you feel small in comparison, then you are stealing from your, yourself, the reality of the success that you've had. And so this sense of what enough is, what you were actually after, what's actually in your

• 10:21Ryan Holiday?

  control, is really, really 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. And the Stoics teach us so much, and 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.

• 10:47Ryan Holiday?

  In 2016, if you had asked me how I thought the next 10 years would go, or how I wanted the next 10 years 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 go like this. I wouldn't have asked for the political disturbances. I wouldn't have asked for things that happened to me personally and professionally. I wouldn't have asked for it to go the way that it did, which is kind of the point, right? 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. One of the things I've come to appreciate from the Stoics, Epictetus talks about this, I think, most movingly, given that he experienced the most adversity of the Stoics,

• 11:29Ryan Holiday?

  is that the key is to wish for things to go the way they have gone, to see them as uniquely faded and designed for you because they have set you up to be who you are. Again, if you had 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. And in fact, if someone else had been in his place in that moment, the world might have turned out very differently. And perhaps if they'd gone the way that he wanted, he would have failed that test and been an underwhelming or a disappointing figure. The key, Seneca says, is that fortune is going to behave exactly as she pleases. Can't be surprised by this. All we can do is prepare. All we can do is be ready.

• 12:12Ryan Holiday?

  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 were looking to spruce up our, our front porch. The weather's finally getting better. We wanted to spend some time hanging out outside with the kids. So we got these awesome hammocks and we actually got them from today's sponsor, Wayfair. If you drove by our, our house, you'd see us out there with our kids reading. We've got this new kitten all hanging out in the hammocks. It's been awesome. And that's because on Wayfair, you'll find quality materials that stand up to real life. They sell furniture and decor that's built to last. And when you shop with Wayfair Verified, it's your shortcut to durable pieces that are hand vetted by product specialists using their 10-point quality inspection.

• 12:56Ryan Holiday?

  They've got thousands of products at every style and budget, whether you're simply replacing an appliance or transforming your home from top to bottom this holiday season. Wayfair's got great reviews as well, so you can find more than 20 million verified five-star reviews from real shoppers. Find pieces made for real life and get even more value with Wayfair Rewards. Join Wayfair Rewards today and get 5% back on every purchase. Head over to wayfair.com to shop all things home. W A Y F A I R dot com.

• 13:29Ryan Holiday?

  Violent threats against executives are growing at an alarming rate. When a company experiences backlash, executives are the first people that are blamed. And people try to track them down through their address, the personal details that are available online. So that backlash can lead right to someone's front door. The team at Ironwall knows this better than anyone. They've protected some of the most targeted executives and individuals on the planet for almost two decades. As a white glove enterprise security service, they protect your people with continuous personal data removal, proactive prevention tools and human-led emergency support. If someone goes looking for your executives, Ironwall ensures they hit a dead end. So here's what to do. Go to ironwall.com/dailystoic.

• 14:13Ryan Holiday?

  You fill out a quick form and you can request a free risk assessment. Their team will show you just how exposed your executives are and how to lock it down before the threat reaches their front door. Ironwall.com/dailystoic. Learn how to stop online threats before they become real world attacks. The link is in the show notes.

• 14:35Ryan Holiday?

  There's no question that Stoicism is an individualistic philosophy. At its core is like, hey, is this up to me or is this not up to me? It's about understanding that you're not the center of the world and you're certainly not the ruler of the world. It's about looking inwards and, and getting a handle on your thoughts, on your actions, on your opinions. But that doesn't mean that a Stoic is the lone wolf. And in fact, as I've seen the popularity of Stoicism grow, I've been dismayed by this version of it that appears particularly on the internet about like, I'm not bothered by anything. I don't care what anyone else does. I don't care about anyone else. You're entitled to your opinion. I'm entitled to mine. We're all these kind of self-contained indifferent individuals. And that's not Stoicism at all. In fact, the Stoics are quite clear.

• 15:18Ryan Holiday?

  We quote them over and over again in the Daily Stoic, like, we are made for each other. To the Greeks, an idiot was not a stupid person. An idiot was a person who is not participating in public life. As I said, Marcus Aurelius talks about the common good 80 times in meditation. So he says, a good life is good character and acts for the common good. That is to say, what are you doing for your neighbors? What are you doing for your community? Not just how are you fighting for you and your family? But how are you fighting for all people? How are you committed to the ideas of justice and duty and responsibility? And 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,

• 16:00Ryan Holiday?

  I've just become much more rooted in that idea. Stoicism is not about needing nobody. It's not about becoming indifferent to everything and everybody but yourself. It is not a recipe for being a better sociopath. It is in fact, a toolkit to be disciplined and strong and courageous in the pursuit of justice, in the pursuit of service, in the pursuit of being a good person who's trying to make a better world.

• 16:30Ryan Holiday?

  One of the interesting things about Daily Stoic as, as a book, accidentally, as a page a day thing, is that it mirrors what Stoicism is supposed to be. It's supposed to be a daily practice. Seneca, in one of his letters to Lucilia, said like, my goal is to find one thing every day, just a little thing that makes me better, that makes me smarter, that fortifies me against poverty, that, that, that helps me prepare for my ultimate death. That's what philosophy was. He's saying that the path to wisdom is these little things, little by little. Xeno said something similar. He said, you know, 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. It could have been exploring them at length.

• 17:12Ryan Holiday?

  But in fact, by being a page a day, one thing every day that you review in the morning or you review at night. And then, you know, of course, people with the Daily Stoic Journal, sitting down and writing about these passages, reflecting on them. That's 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.

• 17:44Ryan Holiday?

  I will tell you, it is a strange experience to pick up something that you wrote 10 years ago when you were in your twenties. Now that I'm in my late thirties. Going through this manuscript and seeing things I wrote a long time ago, I mean, there's parts of it that are mortifying, parts, parts of it that were cringe, parts of it that I understand and think about totally differently. Now, the, the words in here are the same for the most part, although we added some quotes. But I've changed. We never step in the same river twice. This is Marcus Aurelius quoting Herakles. We're always changing. And that's why it's important that we read and reread and read. I just 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. Like, it's not until the middle of the pandemic that I'm reading Marcus Aurelius

• 18:29Ryan Holiday?

  and I just, all these allusions and in some cases, direct references to a plague that he was living in, fully landed with me. It's not until I had kids that I was able to understand just what a theme it was to the ancients in this time of infant mortality, just worrying about your kids, something terrible happening to them all the time and how they would manage that. The point is, there's 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, change and grow with the ideas.

• 19:05Ryan Holiday?

  One of the themes that appears in the Stoic writings more than almost any other theme is this idea of memento mori. Remember, you are mortal. I actually carry this little coin with me, memento mori. 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. And the idea for the Stoics, this meditating on mortality, it's supposed to be sobering, it's supposed to wake you up. I think some people found that depressing. And I, I found it a little depressing at first, but I've come to understand it as I've gotten older, that actually meditating on your mortality, it doesn't just give you urgency, it gives you the present moment. One of the most haunting and in some ways uncomfortable passages from the Stoics, Epictetus and Marcus Aurelius both talk about, as you tuck your children in at night, tell yourself they may not make it until the morning.

• 19:50Ryan Holiday?

  Now, obviously, reading that, before I have kids, I, I guess I took that to mean, hey, attachments can be kind of 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, some scary moments, like during the early days of the pandemic, I've come to understand that what Marcus Aurelius is saying there, what Epictetus is saying there is, 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. So 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.

• 20:34Ryan Holiday?

  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. I only get to do this drive in traffic so many times. Don't rush through it.

• 21:05Ryan Holiday?

  I was just talking to Steve Hanselman, my co-writer, about this. One of the things we wanted to change in the book is that we didn't talk enough about virtue in it. It actually kind of jumps out at me. If I was doing the whole thing over again, I probably wouldn't have split it up into thirds. I would have split it up into quarters. I would have done a quarter on courage, a quarter on discipline, a quarter on justice, a quarter on wisdom. Instead, we have it around these three Stoic disciplines: perception, action, will. But these four virtues are the key to Stoicism. And in fact, it's funny, we didn't have this quote in the original book. But on the October 1 entry, we quote Arius Didymus, who is laying out those four Stoic virtues.

• 21:45Ryan Holiday?

  He says, "There are four primary virtues: practical wisdom, self-discipline, courage, and justice." And that's from Arius Didymus, who was the teacher of the Emperor Augustus, the first Emperor of Rome. Some people know these as the cardinal virtues, and maybe they think because the word cardinal in Christianity that it's about, you know, a high-ranking religious priest. But no, cardinal comes from the Latin cardus. These are the essential disciplines of life. Zeno formulates them for the first time. You know, he says, "These are distinct, yet inseparable virtues." Courage in pursuit of what? Has to be pursuit of justice. How do you know what the right thing is? Well, that gets you into wisdom. How do you know what the right amount of something is? Well, that's discipline and temperance. So all these virtues are related to each other.

• 22:30Ryan Holiday?

  But Stoicism without these virtues, without these ideas, particularly the North Star of justice, is just a recipe, as I've said, for being a better sociopath. And that's not what Stoicism is. The final lesson here, I think, is embodied in these two editions, and then some. This is the first draft, which was itself the result of many, many, many drafts. This is the 10-year anniversary edition. And yet, even sitting in this room, recording the audiobook, there were notes and changes that I was making. 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. When The Daily Stoic came out, I'd been studying Stoicism for a decade.

• 23:12Ryan Holiday?

  Now I'm two decades in, but hopefully, my understanding of it will be better at three decades, and four decades, and five decades. When I do a 25-year anniversary edition, I hope there's even more things to change. I hope there's many new things that I've learned. There's a story about Marcus Aurelius. He's seen leaving his palace. 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, but even as an old man, even as a philosopher king, he is still learning. "I am still learning about Stoicism. I am still reading new things about Stoicism. I'm still understanding these things in a new way." That is the journey. "You cannot learn that which you think you already know," Epictetus said. "If you think you understand it, if you think you got it, if you think you graduated,

• 23:56Ryan Holiday?

  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. Thanks for watching. This is the new edition of the book. You can check it out. If you want a signed, numbered first edition, you can grab that from the link below or at dailystoic.com/ds10.

• 24:32Speaker 01

  When your workday is constantly disrupted, your workflow isn't flowing. It's come to a grinding halt. You don't need an assistant, you need superpowers. Superhuman Go, from the makers of Grammarly, is built for how you actually work. No new tabs, no switching apps, no losing your place. Go handles busy work like finding documents or summarizing email threads, so you can focus on the work only you can do. Try Superhuman Go, from the makers of Grammarly. Find out more at superhuman.com.