Podcast

#128 Ryan Holiday- A Stoic Life

The Knowledge Project

Last highlighted May 18, 2022 Source ↗ ← All highlights

Introduction The knowledge project podcast sharpens your mind by helping you master the best f what other people have already figured out. Ryan holiday is a prolific author in modern philosopher. We talk about how he writes a book a year, how stoicism can help us make better decisions,. The value of journaling and the four virtues, courage, self control, temperance and justice. It’s time to listen and learn. Transcript: Ryan Holiday What I love about Stoicism, what gets me excited about it is that all of the Stoics were active, elite professionals at whatever they did. And Stoicism was a guiding force, a thing that allowed them to do that. To me, what I love about Stoicism is that it’s very much philosophy for the world. I mean, it’s literally founded, one, by a merchant who loses everything in a shipwreck. And two, it’s founded in the Athenian Agora, like in the center of Athens, in the marketplace where it’s battling from day one limited attention from busy people who have actual lives. Shane Parrish Welcome to the Knowledge Project Podcast. I’m your host, Shane Parrish. This podcast sharpens your mind by helping you master the best of what other people have already figured out. If you’re listening to this, you’re missing out. If you’d like special member-only episodes, access before anyone else, transcripts, and other member-only content, you can join at fs.blog Check out the show notes for a link. Ryan Holiday is here today. Ryan is a prolific author and modern philosopher. His books include The Obstacle is the Way, The Daily Stoic, and most recently Courage is Calling. I wanted to talk to Ryan not only to learn more about stoicism and deepen my understanding, but to also learn more about his process for writing and reading. We talk about how he writes a book a year, how stoicism can help us make better decisions, the value of journaling, and the four virtues, courage, self-control, temperance, and justice. It’s time to listen and learn. The Knowledge Project is sponsored by Metalab. For a decade, Metalab has helped some of the world’s top companies and entrepreneurs build products that millions of people use every day. You probably didn’t realize it at the time, but odds are you’ve used an app that they’ve helped design or build. Apps like Slack, Coinbase, Facebook Messenger, Oculus, Lonely Planet, and many more. Metalab wants to bring their unique design philosophy to your project. Let them take your brainstorm and turn it into the next billion dollar app from ideas sketched on the back of a napkin to a final ship product. Check them out at metalab.co. That’s metalab.co. And when you get in touch, tell them Shane sent you. This episode is brought to you by 8sleep. Great sleep is the ultimate game changer. I use this every night and love that 8sleep gives me just the right temperature every time. Fall asleep faster than ever using the Pod Pro Cover by 8sleep. It’s the easiest and fastest way to sleep at the perfect temperature. It pairs dynamic cooling and heating with biometric tracking to offer the most advanced but most user-friendly solution on the market. EightSleep users fall asleep up to 32% faster, reduce sleep interruptions by up to 40%, and get more of a restful sleep overall. It’s the total solution for advanced recovery so you can take on the next day feeling refreshed. You can get $250 off the Pod Pro cover by heading on over to eightsleep.com/Farnham Street. The Knowledge Project is sponsored by Fellow.app. Arguably the biggest time waster for me in business is an unproductive meeting. You know, the ones that have no agenda, no clear takeaways, and no accountability. After selling his last company, my friend Aiden swore that he would never attend another meeting without an agenda. He adopted this motto, no agenda, no attenda. So Aiden and his co-founders built a tool to make meetings productive and delightful for everyone. It’s called Fellow. It’s simple, it’s beautifully designed, and it helps you stay organized by connecting your calendar to collaborative meeting agendas and action items. It’s a game changer for all your one-on and team meetings. And the best part, you’ll never have to attend a meeting without knowing exactly what the purpose is, who’s going to do what, and what the outcomes are. Go to www.fellow slash Shane to get 60 days of free access. Again, that’s fellow.app slash Shane for 60 days of free access. Let’s start with your book writing process. You’re prolific, man. You do like a book a year. How do you do that? (Time 0:00:00)
Is There a Daily Cost to Getting Longer? Exercising might be an hour a day cost, but it’s going to improve the odds that you can do what you do longer. The real cost is not money, it’s in how many years of being able to do this it cumulavely deprives you of,. let leswitch gers, the little bacas. I’ve got to imagine, like a fierstaf curry, having a father who is a professional athlete helps you understand this. Most of the time, though, you’re a first generation at whatever you do, especially at like, the alete level. Transcript: Shane Parrish The other point that you mentioned a while ago was sort of longevity, which I think is often something where we have to pay a cost today to get longevity, but we don’t want to pay that cost. An example is sort of like eating healthy might be difficult for you. It’s not for you personally, but like exercising, right? So exercising might be an hour a day cost, but it’s going to improve the odds that you can do what you do longer. And if you look at the best sort of like professional athletes, their entire life, like Tom Brady’s life is organized around playing football as long as you possibly can. And whatever support staff that needs from like a personal chef to sort of his personal trainer and all of this being involved in his life. Like he looks at that as like, this is enabling me to do what I do. I need to work out every day. I need to stretch. I need to get a massage. I need my life organized in a way that’s maximizing that. And he’s also looking at it from longevity, right? So there’s a daily cost to this stuff where you might be able to maximize your sort of like immediate value by writing twice as fast, burning yourself out, you know, killing your marriage, Not seeing your kids, and you get these immediate rewards. And we often sort of like, I feel like we have this conversation with ourselves. And we say, Oh, I’m going to do it until I reach this point. And then I’m going to quit, right? Like, I’m just going to do it for this book. But like, as you said, that appetite is sort of never fulfilled and you can never walk away. And then you sort of end up burning out and flaming out, which limits your, you know, where you reach your potential and limits what you’re capable of doing. Ryan Holiday I worked on this book. I know you had them on the pockets with Chris Bosch. And one of the things I was asking him about for letters of a Young Athlete, because I’d heard that LeBron James, you know, spent something like a million and a half dollars a year on his Body, like trainers, massages, medical treatments, etc. And he was like, Oh, yeah, it was crazy. You know, the rest of us were like, we’re young, we don’t care. We want to we want to play video games on the plane. And he’s like doing yoga, he’s taking ice. You know, he was he was always doing. And here he is still playing. And the rest of the big three is not in the league anymore. A certain amount of that is luck. Like, obviously, you know, Tom Brady has the benefit of not getting hit to the degree that other quarterbacks have or no real catastrophic injuries. But the investment in the body and sustainability is like really huge. I’ve got to imagine like if you’re Steph Curry, having a father who is a professional athlete helps you understand this is like you come from a lineage of people who’ve done this before. Most of the time, though, you’re a first generation at whatever do, especially at like the elite level. So it’s hard to like really pick up these sort of pro habits, whether it’s investing or hiring or scaling or shortcuts or, you know, taking care of yourself. But like you have to figure these things out because the real cost is not money. It’s in how many years of being able to do this it cumulatively deprives you of. Shane Parrish Let’s switch gears a little bit because (Time 0:38:09)
How Do You Decide the Problem? “I do tend to find we often spend too much time thinking about the decision, instead of just fucking making it and dealing with the consequences,” he says. “As a writer, for instance, i like to do things in order… But if you’re telling me that i’m starting to get damned up over here, i’m n a pivot.” The author is currently working on a book about self discipline. Transcript: Shane Parrish I want to get into some more meaty questions here. What do you know about making decisions that most people miss? Ryan Holiday I do tend to find we often spend much time thinking about the decision, instead of just fucking making it and dealing with the consequences of it. So I there’s a story I tell about George Marshall, where he goes, don’t fight the problem, decide the problem. So I tend to find in my thing, like, I’m a big believer in momentum. And I’m a big believer in crossing things off list. So sometimes this costs me because I’ll be hastier than I should have been. But like, what will be frustrating to me, especially with someone I work for, I’d be like, I’ll bring something up, be like, hey, you have to decide whether we’re doing this or this, right? And then like, three days later, three months later, I’ll check in on and they’ll be like, Oh, I’m still thinking about it’s like, okay, but you just cost us three months of not having It either way. And whatever the margin of error would be between one decision or the other is far smaller than whatever the opportunity costs of not having it done and moved on to the next thing are. Shane Parrish Totally. Do you want to go a little deeper on that in terms of like momentum and how that works for you and how you think about that in the context of decision making? Ryan Holiday Well, so as a writer, for instance, I’m all about momentum. So every day, like I told you about how I sort of work on books, but I break each thing up into smaller pieces. And so I want to have the sense that I’m things off, that I’m making forward progress. Let’s say I have a bunch of chapters that are right for this section. Now, there’s one section that I kind of knew what I wanted to do. And another section that I could do it this way. I could do it this way. I don’t really have the right example. Am I going to do the hard one first or the easier one first? In this case, I’m going to do the easier one first because stalling out is the main thing that I want to avoid. It’s not that I’m going towards the path of least resistance, but I’m going towards where I’m going to make forward progress. And so I like to do things in order. For instance, I like to do them according to plan. But if you’re telling me that I’m starting to get damned up over here, I’m going to pivot and maybe I will flash forward. And like the book that I’m working on now, which is about self-discipline, I didn’t have enough material to write the main chapter for the second part of the book. But I did know all the subsequent chapters I was going to write in the book. So I started with the subsequent chapters and then only last week did I circle back to put in the main thing. So instead of stalling out, going like, I can’t write until I do all this stuff, I wanted to have the forward momentum while I was working on the other stuff. So I’m just a big believer in momentum in that sense. Going (Time 0:41:17)
How to Accept the Things We Can’t Control? “How do we learn to accept the things we can’t control? I mean, you don’t really have any choice, i guess,” she says. “I think what the stoics are saying is, like, excepting that that it’s a fact on the ground does not lessen your obligation to prevent it from happening in the future.” She also talks about how idealistic people often put their preoccupation with how they want things to be puts them at odds with how they are. Transcript: Shane Parrish Back to stoicism a little bit, how do we learn to accept the things we can’t control? Ryan Holiday I mean, you don’t really have any choice, I guess. Like we have to go, well, I can’t accept this. And it’s like, well, does not accepting it mean that it didn’t happen? So what we’re really talking about is like the Stoics, they use this word ascent, not like ascent up a mountain, but A-S And it just means like you’re acknowledging that it happened. You’re like giving it permission to have happened. So when we’re talking about, well, I can’t accept things that are outside my control. You have accepted them. They have happened. You had no choice. Like no amount of objecting undoes them. What we’re really talking about is like whether mentally you’re OK acknowledging that they happened or that you’re at peace with the fact that they happened. And so if we think about it like that, I do think it becomes a little easier. Shane Parrish What about like sort of the people that focus continuously on? I’m thinking like the way the world should work versus the way the world does work. Yeah. Ryan Holiday This is like an important part of stoicism too, because if you have high standards, it’s very easy to expect other people to live up to those standards. And invariably they do not, right? I think we struggle with acceptance because it feels like you are saying that because it happened, it’s like good that it happened or that it should have happened. Right. When really, I think what the Stokes are saying is like accepting that it that it’s a fact on the ground does not lessen your obligation to prevent it from happening in the future, or it Does not mean that it was okay, like that it wasn’t immoral or unjust that it happened. Saul Alinsky, the activist says like, you know, the social organizer has to start with the world as it is for what it is, if they want to change it. I think the problem with a lot of idealistic people, particularly people who are interested in social change or social justice, is that their preoccupation with how they want things To be puts them at odds with how they are and actually makes it much less likely that you’ll be able to do anything with it. Look, I’m fascinated with ancient philosophy. If you told me I could write books that are much headier and go off into the weeds because everyone was well-versed in the basis of philosophy and we could have these really high-level Discussions about it, that would be cool with me. I mean, I would probably prefer that. But the reality is most people are not interested in philosophy. And so if I want to speak to them about philosophy, I have to meet them where they are and write and communicate accordingly. It’d be great if everyone spoke this language, but they speak this language. So talking to them in the language of your choice isn’t going to communicate what it is that you feel needs to be communicated. It is what it is. There’s (Time 0:44:08)
How to Accept the Things We Can’t Control? “How do we learn to accept the things we can’t control? I mean, you don’t really have any choice, i guess,” she says. “I think what the stoics are saying is, like, excepting that that it’s a fact on the ground does not lessen your obligation to prevent it from happening in the future.” She also talks about how idealistic people often put their preoccupation with how they want things to be puts them at odds with how they are. Transcript: Shane Parrish Back to stoicism a little bit, how do we learn to accept the things we can’t control? Ryan Holiday I mean, you don’t really have any choice, I guess. Like we have to go, well, I can’t accept this. And it’s like, well, does not accepting it mean that it didn’t happen? So what we’re really talking about is like the Stoics, they use this word ascent, not like ascent up a mountain, but A-S And it just means like you’re acknowledging that it happened. You’re like giving it permission to have happened. So when we’re talking about, well, I can’t accept things that are outside my control. You have accepted them. They have happened. You had no choice. Like no amount of objecting undoes them. What we’re really talking about is like whether mentally you’re OK acknowledging that they happened or that you’re at peace with the fact that they happened. And so if we think about it like that, I do think it becomes a little easier. Shane Parrish What about like sort of the people that focus continuously on? I’m thinking like the way the world should work versus the way the world does work. Yeah. Ryan Holiday This is like an important part of stoicism too, because if you have high standards, it’s very easy to expect other people to live up to those standards. And invariably they do not, right? I think we struggle with acceptance because it feels like you are saying that because it happened, it’s like good that it happened or that it should have happened. Right. When really, I think what the Stokes are saying is like accepting that it that it’s a fact on the ground does not lessen your obligation to prevent it from happening in the future, or it Does not mean that it was okay, like that it wasn’t immoral or unjust that it happened. Saul Alinsky, the activist says like, you know, the social organizer has to start with the world as it is for what it is, if they want to change it. I think the problem with a lot of idealistic people, particularly people who are interested in social change or social justice, is that their preoccupation with how they want things To be puts them at odds with how they are and actually makes it much less likely that you’ll be able to do anything with it. Look, I’m fascinated with ancient philosophy. If you told me I could write books that are much headier and go off into the weeds because everyone was well-versed in the basis of philosophy and we could have these really high-level Discussions about it, that would be cool with me. I mean, I would probably prefer that. But the reality is most people are not interested in philosophy. And so if I want to speak to them about philosophy, I have to meet them where they are and write and communicate accordingly. It’d be great if everyone spoke this language, but they speak this language. So talking to them in the language of your choice isn’t going to communicate what it is that you feel needs to be communicated. It is what it is. There’s (Time 0:44:08)
How Can We Learn To Manage Anger? How can we learn to manage our anger? I was thinking about this with a course that we made for daily stoic. The question about anger is, like, does it actually make you better at what you do? It may in the short term, right? And usually i tend to find that it’s pretty corrosive fuel. Transcript: Shane Parrish Going on to the next sort of topic, how can we learn to manage our anger? Ryan Holiday I was thinking about this with a course that we made for Daily Stoic. I was saying that like, just because you don’t have an anger problem doesn’t mean that anger is not a problem for you. Right? Like when I look at most of the mistakes that I made, most of the things that I regret, most of the things that I wish I could undo, usually anger is a pretty big part of that, right? Like anger was a driving factor in why I wrote the email and sent it, right? It was why I chose not to do X, Y, or Z, you know, it’s why I was speaking this way or that way. So I think, you know, the question about anger is like, does it actually make you better at what you do? It may in the short term, right? And to go to our point earlier about sustainability, is it fuel that can get you where you want to go over the long term or is it really corrosive? And usually I tend to find that it’s pretty corrosive fuel. So I think if we just start with like, let let me make sure I’m not lying to myself about my temper. Right? Because a lot of us tell ourselves like, oh, it’s because I really care or it’s what drives me. I’m not as bad as my boss or my dad or whatever. But like, if you really step back and you said like, what is this actually adding and what are the costs that it’s coming at? It usually becomes pretty illustrative that it’s not a positive force in our lives. What (Time 0:50:08)
The Key to Learning and Improvement is Reflection Journaling is the conversation we have with ourselves about who want to be and how far we are from that at any given moment. It’s also the codification of what we’ve learned, like anne frankline says: paper is more patient than people. And so instead vomiting that all over someone a, you know, because they left the tooth paste cap out, you processed it, and then you were just like, hey, i feel like we’re not in sink. What’s going on, right? Instead of like, what the fun is this?” Transcript: Shane Parrish Of the things a lot of the Stoics have in common, at least like Marcus Aurelius and a lot of, or maybe not Stoics, but more prominent people in life is that they journal. Ryan Holiday Yes. What we’re talking about is a lot of like sort of self-awareness and self-criticism, right? The sort of evaluation of how one is doing and how one could do better. And I think journaling is pretty much the most effective way we’ve found to do that. I mean, I think it’s a little bit there in meditation, but I mean, part of meditation is not thinking, right? And so I think journaling is just, as I have experienced it and I understand it, journaling is the conversation we have with ourself about who want to be and how far we are from that at any Given moment. Shane Parrish And I think that’s necessary from a reflection point of view, because I think one of the keys to learning and improving is not just sort of having this experience. It’s actually your reflection on this experience is what’s going to cause you to create an abstraction. And the abstraction is going to be your action. So if you think of learning as a loop, right, you have an experience. It could be yours. It could be this conversation that you’re listening to. It can be a book that you’re reading. It can be somebody at work. But the real key to that learning becomes the reflection. Like what were the variables that mattered? How do I digest this? How do I process this? How do I distill it? And so often what we do in day-to life is we consume other people’s abstractions without the reflections. And so we have this illusion of knowledge. So when we’re journaling, what we’re doing is we’re teasing out that illusion of knowledge, but we’re also taking our experiences and we’re translating them actively into sort of Abstractions that we can use that become actions that we can take. Ryan Holiday Well, look, it’s I think it’s also the codification of what we’ve learned. So like for a sports analogy, if just like instruction and then experience was enough, why would players ever watch game film, right? Like they were there when it happened. Obviously, they know what happened, but it’s not true, right? You break it down. You need to look at it minutely. You need to evaluate yourself, not in the moment, but from a distance. And I think it’s in the pages of a journal that we have the ability to go, well, here’s what you want to be, but here’s who you were today. You knew today was a travel day and you thought about not being anxious, you know, being patient, going with the flow. And here we are the next day or that evening. And you’re like, but you had a meltdown, didn’t you? Right. Why did that happen? What triggered you? What could you do differently next time? How do you think other people saw this? Right. And so that sort of ability to reflect and analyze and discuss is really important. And I think the other part is it’s not just our behavior. There’s an Anne Frank line I love where she says paper is more patient than people. It’s also like the things that I’ve thought or believed or been frustrated with people about that I’ve kept like by writing them down in the journal, I felt like all the all the ferocity Of that feeling went away. And so instead of vomiting that all over someone, you know, because they left the toothpaste cap out, you processed it. And then you were just like, hey, I feel like we’re not in the sync. What’s going on? Right. Instead of like, what the fuck is this? You know, like, so, so you’re able to, you’re able to, to, to get it out in a safe place. It (Time 1:01:24)
The Indecision Make Is Taking You Out of System Writes the decision down at night that you’re about to make, then read it in the morning and see if it still makes sense. Lincoln would write these letters that he would leave in the drawer of his desk rit and almost never send. And so i think about like, there’s almost never been aa like a firm or a strict or, a negative like mal that i’ve had to send that I haven’t made some changes to. Transcript: Shane Parrish Also sort of slows you down, right? So in decision-making, we, we advocate sort of an approach when we work with people on improving their decision-making about write the decision down at night that you’re about to make And then read it in the morning and see if it still makes sense to you. And what you’re really doing is you’re doing a couple of things, right? Like you’re processing whether you comprehend that in a way that you can explain it to yourself. You’re checking in with your rational and emotional self. You’re taking yourself out of system one. You’re putting yourself in system two when you go the night and you read it in the morning. Most of the time you’re like, oh, that, you know, maybe that doesn’t make sense or that wording isn’t quite right. And you can sort of self-correct. And I think that it also helps you reflect on the decision. What are the variables that matter? How are you thinking about it? And you’re getting out of that sort of like instinctive response and you’re putting yourself in a situation where you’re improving the odds that you’re at least using reasoning. Ryan Holiday No, and this is true in communication as well. Like the two or three biggest scandals of Truman’s presidency are basically letters. He was a reasonably controlled and decent person, but when he got upset, he would write say things that he shouldn’t say, that upon reflection, he regretted saying, but he’d already Put it in the mail by the time that reflection could have happened. Lincoln, conversely, would write these letters that he would leave in the drawer of his desk, right? And almost never send. And so I think about like, there’s almost never been a, like a firm or a strict or a negative like email that I’ve had to send that upon sitting on for 24 hours or sometimes like a week that I haven’t made some changes to. That’s not to say that I don’t send it. I almost always do send it. But I just realized that what was talking was less me trying to solve the problem and me venting about the problem. And I’m not even saying it fixed the situation. But I think about it, it’s like, look, they’re still probably going to be an asshole in response to what I have to say. If they were, if they weren’t, we probably wouldn’t be having this conversation. But I know that if someone else were to look at it, if I were to evaluate it against my own conscience, if it were to be public, that I know that I didn’t provoke this, that this came from them. And there’s no evidence that no one can go, hey, you’re both to blame here, right? Because I took the time to reflect, be in control of myself and not let passion dictate. (Time 1:04:57)