These 3 Books Changed My Life Completely

On today’s episode, Ryan discusses the 3 books that completely changed his life. Listen to find out what books had such a great impact on Ryan’s thinking, and why re-reading important books can give you new insights. This episode is also brought to you by HelloFresh, the meal-kit subscription that gets you healthy and delicious home-cooked meals, right to your doorstep. HelloFresh sends you meal kits in a way that fits in with your schedule and dietary preferences. Meals are seasonal and delicious, and save you and your family time and money on grocery shopping. Visit HelloFresh.com/stoic80 and use code STOIC80 to get $80 off, including free shipping.***If you enjoyed this week’s podcast, we’d love for you to leave a review on Apple Podcasts. It helps with our visibility, and the more people listen to the podcast, the more we can invest into it and make it even better. Sign up for the Daily Stoic email: http://DailyStoic.com/signupFollow @DailyStoic:Twitter: https://twitter.com/dailystoicInstagram: https://www.instagram.com/dailystoic/Facebook: http://facebook.com/dailystoicYouTube: https://www.youtube.com/dailystoicSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. 📢 Share | ⚙️ Manage Subscription

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

• 0:02Ryan Holiday?

  Welcome to the weekend edition of The Daily Stoic. Each weekday, we bring you a meditation inspired by the ancient Stoics, something that can help you live up to those four Stoic virtues of courage, justice, wisdom, and temperance. And here on the weekend, we take a deeper dive into those same topics. We interview Stoic philosophers. We reflect, we prepare, we think deeply about the challenging issues of our time, and we work through this philosophy in a way that's more possible here when we're not rushing to work or to get the kids to school, when we have the time to think, to go for a walk,

• 0:44Ryan Holiday?

  to sit with our journals, and to prepare for what the future will bring.

• 0:52Ryan Holiday?

  Hey, it's Ryan. Welcome to another weekend episode of The Daily Stoic. Today's episode is me riffing on three books that, if you've been paying attention, you've probably heard of. If you've been putting off reading, you should stop that. One is one of my favorite novels. One is one of my favorite nonfiction books. And the other is, I think, the greatest philosophy book ever written. And so I go into these books. I just thought it'd be fun to talk about why these things have resonated with me, the value you can get out of them, my interactions with them over time. I think one thing I don't talk quite enough about in this little session,

• 1:34Ryan Holiday?

  so I thought I'd preface it, is the idea of reading and rereading and rereading. I have a shelf behind my desk that I call sort of my life shelf. And these three books, each one of them sits prominently on that shelf. And by life, I mean they're books that... Not just guide you through life, but books you have to read throughout your life because you get something different from them each time. You know, when I read The Great Gatsby in high school, Gatsby struck me as heroic. When I read him in my twenties, it struck me, you know, slightly different. And when I read it again some more recently, you know, there was a tragic element that I that I experienced a bit more. And I I also thought a lot more about Nick Carraway.

• 2:17Ryan Holiday?

  And I I noticed there's a great little line about parenting at the beginning of that book. And it's not just because I've changed and I've gotten older, but I've read other books about Fitzgerald, about the twenties, about bootlegging, even even the, you know, I opened my book Conspiracy with a chunk, an observation that came from probably not the first, certainly I didn't notice this little observation the first time I read Gatsby in, you know, 11th grade. It was it was the reading and the rereading. And now I just have a much more complicated, but but profound connection with the material, with the characters and all of that. So it's not just about reading, but it's about rereading. And so even if you've read all three of these books, which I've got to imagine I've raved

• 3:01Ryan Holiday?

  about them enough times that that some of you listening have, but hopefully in hearing me describe why they've resonated with me, you'll see them from a slightly different or new angle, and the experience will even be more powerful. And maybe you'll be able to recommend them better to other people. So here are three books that you must read.

• 3:28Ryan Holiday?

  Everyone has a book that's changed their life, like something that just sort of hits you. Tyler Cowen calls them quake books, something that sort of shakes your whole existence. So I was thinking like three quake books that have changed my life. The first one, 40 Laws of Power.

• 3:44Ryan Holiday?

  I read this when I was in high school. I've gone through a bunch of copies. Someone stole my copy when I was working at American Apparel, which was the perfect place to read a book like this. The CEO of a company used to say, "Look," he would quote one of the laws. He said, "Look, we do good stuff for people. We make stuff in the US. But ultimately, people only buy our clothes because they like our clothes. Always appeal to self-interest, never mercy or gratitude." So again, you can be a good person in the world. Not that Dove was by any means that. But he was doing good because it aligned with the 48 Laws of Power, and that's an essential thing. So I've read this book dozens of times. It's been great. First law of The Law of Power, which I love, is "Never outshine the master. Always make those who feel above you comfortably superior. In your desire to please and impress,

• 4:29Ryan Holiday?

  do not go too far in displaying your talents, or you might accomplish the opposite: inspire fear and insecurity." So there's just a bluntness there where, you know, one of the laws is "crush your enemy totally" or "let others do all the work and take all the credit." So those obviously feel like deeply immoral things. Robert, who I've gotten to know, says they're not immoral, they're amoral. If I said, "Hey, gravity pulled an old lady down, shattered her hip, and then she died." Or "gravity pulled an airplane out of the sky, and everyone on board was killed." That feels deeply cruel, but we know that gravity simply is what it is. We don't have an opinion about gravity. We just accept it and we accommodate. And that's really like what the 48 Laws of Power is.

• 5:12Ryan Holiday?

  48 Laws of Power is about gravity, the rules of life. So Robert isn't saying you should steal work from other people. He isn't saying you should be the insensitive master who never lets anyone outshine them. He says you have to be aware, as you're working for someone, that they see themselves as the master. And if you're not careful, you will unintentionally offend them, and that may be your ruin. Right after college, I worked at this talent management agency, and I kept a copy of The 48 Laws of Power on my desk as I was working for Robert Greene. And in reading it, I raised some eyebrows. And one of the bosses started to get very paranoid, and ultimately, he and I ended up on a collision course. And I got fired. I was, even as I was studying The 48 Laws of Power, unfairly a victim of them.

• 5:54Ryan Holiday?

  So to me, the concept of the 48 Laws of Power is morally justified even just as as defense. What you really get from the 48 Laws of Power is a masterclass in history. You know, how to create compelling spectacles, how to make people realize what your worth is to them. How to deal with, you know, insecure people, how to how to counteract ego, how to how to just do all the things that you need to do in life. And there's so many good laws. Enter action with boldness, plan all the way to the end, make your accomplishments seem effortless. Play to people's fantasies, recreate yourself, keep your hands clean, concentrate your forces. Look, these are not morally dubious things at all. They're just things you have to understand if you want to be successful in the world.

• 6:36Ryan Holiday?

  So I think everyone who's trying to do anything that depends on other people, anyone whose job depends on the crowd, anyone whose job depends on the approval of a boss or banks or the media, you have to understand this book. And if you don't understand it, you are constantly going to be defeated, demoralized, outsmarted by people who intuitively or explicitly are following the principles of this book. So if you haven't read the 48 Laws of Power, you don't understand that the gravity that is operating in the world you're on. And you're going to be at the mercy of these unseen forces.

• 7:11Ryan Holiday?

  I wanted to go to my favorite novels, my favorite novel, What Makes Sammy Run by Bud Shulberg. You can see all the notes that I took here. Actually, the conclusion of my book, The Obstacle is the Way, is all about it. But this is a novel I've read three or four times now. I read it when I was 19. My mentor said, hey, you've got to read this book, and I did. And it just hit me in exactly the same place. To me, this is a book that that pairs well with the 48 Laws of Power. Forty Laws of Power is about ambition. And the novel What Makes Sammy Run is a cautionary tale about ambition. A guy gets everything he wants, but who does he have to become in order to do that? And basically sells his soul to do it. There's this great line in the book, he says, what a beautiful, bright light ambition can be when there's something behind it.

• 7:55Ryan Holiday?

  And would it puny? Flickering sparkler it is when there isn't. But ultimately, I'll spoil the ending. It's this great sort of Hollywood tale. It's kind of an Ari Gold-esque character. But if I spoil the ending, basically at the end, we think like, hey, somebody who follows the 48 Laws of Power, who's cruel, merciless, who does whatever it takes to win, ultimately, they'll get what's coming to them, right? Basically, at the end of the novel, the narrator is summoned to Sammy's house, and Sammy's just married like the most beautiful girl in Hollywood. And the narrator's just like, "I thought how unconsciously I had been waiting for justice to rise up and smite him with all its vengeance, secretly hoping to be around when Sammy got what was coming to him. Only I had expected something conclusive and fatal, and now I realize that what was

• 8:40Ryan Holiday?

  coming to him was not a sudden payoff but a process, a disease he had caught in the epidemic that swept over his birthplace like a plague, a cancer that was slowly eating him, the symptoms developing and intensifying success, loneliness, and fear, fear of all the bright young men, the newer, the fresher Sammy Glicks that would spring up and harass him, to threaten him, and finally overtake him. It was too late to hate or change him. He just was who he was."

• 9:13Ryan Holiday?

  What I think is the best book ever written, Marcus Aurelius's Meditations. I strongly recommend the Gregory Hayes translation. It's the most lyrical, the most accessible, and it's just, it's just an incredible document to think. I mean, so first off, this is a private journal, never intended to be published, and Marcus is writing to himself, and yet he opens it with debts and lessons. He opens it with gratitude, that he learned character and self-control from his grandfather, that he learned not to waste time on nonsense from someone. He learned kindness from Sextus, an example of fatherly authority in the home, what it means to live as nature requires, gravity without errors. This is my favorite line, he says, "To not display anger or other emotions, to be free

• 9:57Ryan Holiday?

  of passion yet full of love." So he writes, the beginning, it's just, he's just reiterating to himself the lessons that he's learned about the person that he wants to be, but then... He opens Meditations with Ivan, one of the great passages in all of history. "When you wake up in the morning, tell yourself the people I will deal with today will be meddling, ungrateful, arrogant, dishonest, jealous, and surly." But he's not just listing that people suck, and then he goes, "And they are like this because they don't know good from evil, and you have to understand that, and you can't let them implicate you in their ugliness." And to me, that's what Stoicism demands of us. That's who we're supposed to be as people. We're supposed to understand what the world is, but not be dragged down or destroyed by it. I think Marcus encapsulates all of Stoicism in this book.

• 10:42Ryan Holiday?

  He says, "Objective judgment now at this very moment, unselfish action now at this very moment, willing acceptance now at this very moment of all external events." That's all that you need. In case you think Stoicism is selfish, he says, "What injures the hive injures the bee." In case you think that Stoicism is about trying to become king, trying to become emperor, no, he says, "Ambition means tying your well-being to what other people say or do. Self-indulgence means tying it to the things that happen to you. Sanity means tying it to your own actions." It's also about self-control, though. He goes, "You don't have to turn this into something. You don't have to have an opinion about this." So in Meditations, what you get is just the wisest man of the world talking to himself about how to be a better person. And that's, to me, what Stoicism is about.

• 11:27Ryan Holiday?

  You're studying Stoicism, you're reading Marcus Aurelius, because it makes you better as a human being. You know, and it's incredible to think Marcus was writing this book during the Antonine Plague, 15 years of a horrible pandemic. He lost some of his own children, he lost friends. And yet Marcus goes, "No, it's not unfortunate this happened." He says, "It's fortunate that it happened to me, because I've remained unharmed by it, and that I can use this. Other people would have been shattered by it, but not me." A plague can kill you, but it only harms you if it destroys your character. He means that literally and figuratively. So, you know, I was lucky enough to read this book. I was 19 years old. This is my copy, I got it at Borders. You know, it just hit me in so many ways. He says, "It stares you in the face. No role is so well-suited to the philosophy you're in right now."

• 12:11Ryan Holiday?

  And that meant me as a college student, that meant... Me as an aspiring writer later on, that meant me as a husband. That means me as a father. That means me as a writer and an entrepreneur now. Everything we do is a chance to practice philosophy. And I think Meditations is all about that. And no one has perhaps written better or more eloquently about philosophy. And perhaps no one has been made better by philosophy more than Marcus. It's perfection of character to live your last day, every day, without frenzy or sloth or pretense. That's what Meditations is about. That's what we're doing. It says, "Straight, not straightened. Let it happen if it wants to whatever it can happen to.

• 12:53Ryan Holiday?

  It can't hurt me unless it, I interpret it's happening as harmful to me and I can choose not to." And then, this one has stayed with me in life, it says, "Don't be ashamed to need help. Like a soldier storming a wall, you have a mission to accomplish. And if you've been wounded and need a comrade to pull yourself up, so what?" And to me, this book is the perfect comrade. It's the perfect friend to open yourself up to. You get something new every time you open it. If you haven't read Meditations yet, you should. Don't get a free internet translation. Read the Gregory Hayes translation, although we have some good translations in The Daily Stoic as well. Look, again, greatest book ever written, I think. My favorite novel, What Makes Sammy Run. And I think one of the best nonfiction books of all time, one of the best looks of power

• 13:36Ryan Holiday?

  of all time, Forty Eight Laws of Power by the great Robert Greene. Read these three books. Can't do better than that. Hey, it's Ryan. Just a few days left to sign up for the Daily Stoic New Year, New You Challenge. It's our best thing. You get 21 custom challenges, almost 30,000 words, almost a full book's worth of content. You get a printable calendar. There's going to be a weekly check-in call from me. You get access to our Slack channel. Look, Marcus Aurelius says, "You could be good today, instead you choose tomorrow." Epictetus says, "How much longer are you going to wait to demand the best of yourself?" Will you do this with us? We'd love to have you. I'll be doing it there alongside everyone. It's one of my favorite things. I have all sorts of habits that I got from last year's and the year before, the other

• 14:21Ryan Holiday?

  challenges we've done. And remember, if you sign up for Daily Stoic Life, you get this challenge and the other ones for free. So I'll see you. Sign up at dailystoic.com/challenge.