The School of Greatness - How Fortune Favors The Brave w/Ryan Holiday EP 1171

Episode Date: October 4, 2021

My guest today is Ryan Holiday. He’s one of the world's foremost writers on ancient philosophy and its place in everyday life. His books The Obstacle Is the Way, Ego Is the Enemy, The Daily Stoic, a...nd Stillness Is the Key have sold millions of copies and been translated into over 30 languages. He’s now written a new book called Courage is Calling: Fortune Favors The Brave.In this episode we discuss how fear is actually a good thing, why people struggle to have courage and how to overcome that, how thinking about our own mortality can help us rather than hurt us, the biggest lessons we can learn from stoicism when it comes to finding peace, wealth, developing discipline, and so much more!For more go to: www.lewishowes.com/1171Check out his website: www.dailystoic.comDaymond John on How to Close any Deal and Achieve Any Outcome: https://link.chtbl.com/928-podSara Blakely on Writing Your Billion Dollar Story: https://link.chtbl.com/893-pod 

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Starting point is 00:00:00 This is episode number 1171 with New York Times bestselling author Ryan Holiday. Welcome to the School of Greatness. My name is Lewis Howes, a former pro athlete turned lifestyle entrepreneur. And each week we bring you an inspiring person or message to help you discover how to unlock your inner greatness. Thanks for spending some time with me today. Now let the class begin. Welcome back, everyone. My guest today is Ryan Holiday.
Starting point is 00:00:32 He is one of the world's foremost writers on ancient philosophy and its place in everyday life. And his incredible books, The Obstacle is the Way, Eagle is the Enemy, The Daily Stoic, and Stillness is the Key have sold millions of copies and been translated into over 30 languages. And he's now written a new book called Courage is Calling, Fortune Favors the Brave. And in this episode, we discuss how fear is actually a good thing for us, why people struggle to have courage and how to overcome that in your life, how thinking about your own mortality can help us
Starting point is 00:01:05 rather than hurting us, the biggest lessons we can learn from stoicism when it comes to finding peace, wealth, and developing discipline, and so much more. And if you're enjoying this, make sure to share this and spread the message of greatness to a friend that you think would be inspired by this as well. And if this is your first time here, click the subscribe button over on Apple Podcasts right now and leave us a rating and review, letting us know the part of this episode you enjoyed the most or the part that really inspired you the most. And a big shout out to the fan of the week. This is from Susie who left a review over on Apple Podcast that said, this podcast continues to inspire and change my life. It's educational. It's therapeutic. Thank you, Lewis
Starting point is 00:01:43 and Team Greatness. Every time I listen, there's always a takeaway. Definitely one of my favorite podcasts. And to add, I don't usually leave reviews. So that's how much this show has helped me. So big thank you to Susie for being the fan of the week. We appreciate you and your constant support. Okay. In just a moment, the one and only Ryan Holiday. Welcome back, everyone, to the School of Greatness. Very excited about my guest, Ryan Holiday, in the house. My man.
Starting point is 00:02:13 Good to see you. So good to see you. You are changing millions of people's lives with your book, with your work, with your articles, with your content. Now you're this YouTube star as well. Have you even known each other for 10 years? I was thinking that. I was like, when did I meet you? It was like 2011, I think.
Starting point is 00:02:29 Was it Tim Ferriss' event, 2011? Neither of us had books. Neither of us had online platforms in any way. Both of us had big EOs. And then you wrote. I don't know about that. But I do think sometimes people think like that either it's random luck that you just get lucky or they think it's like impossible to do.
Starting point is 00:02:51 And I would say it's a good example that neither of those things are true. Right. And we've been consistent for, well, previous than 10 years. I mean, we were working very hard to get to where we were 10 years ago. Yes. But the last 10 years have been constantly showing up, self-discipline, consistency,
Starting point is 00:03:10 surrounding yourself with people wiser than ourselves. For sure. And overcoming fears, leaning into courage to put ourselves out there, taking risks. Yeah, I mean, like, so I identify as a writer that's the medium that i'm comfortable in that's like what and part of the reason i feel like i gravitate towards
Starting point is 00:03:31 writing is that i was less comfortable like being up in front of a room or putting myself out there like i wasn't a kid who like wanted to be in drama class or like be in front of people i was the quiet introvert writer so like even within the thing that you're good at, you're immediately, like the irony of success in any field is that it forces you to do a bunch of things that you are not good at. That are scared of.
Starting point is 00:03:57 Yes. So it's like you write, you think like, oh, now my job is writing. It's like, actually, no, you have to go talk about what you wrote in front of large groups of people
Starting point is 00:04:06 or you have to make videos. So like, all of that stuff, yeah, so as far as overcoming fear, it's like. It's kind of like the idea of the artist,
Starting point is 00:04:13 like the most talented musician in the world who's undiscovered who just like plays in his basement. You have to, you can't just become a master of your craft.
Starting point is 00:04:22 You have to learn how to promote yourself, put yourself out there, create content. Yeah. Be in relationship with managers, do deals and not rub people, show up on time, like all these other things you got to learn in order to get your craft out there. When you talk to writers or anyone like creatives, I just love doing this stuff. I just like, it's good.
Starting point is 00:04:40 It should just find its audience. Never works. I see it as like two consecutive marathons. So like you run the marathon, you win. You think they're like, oh, great job, Lewis. Like here's your medal. And you think they're like leading you over to the podium to like, you know, stand in front of everyone. And they're actually just leading you over
Starting point is 00:04:56 to like the second marathon that starts right now. Right now, start running. Yes, just back-to-back marathons, like making it, you put everything you had into it. You put your whole life on pause. You gave everything. You have nothing left. And if you do have something left, then you cheated.
Starting point is 00:05:12 You didn't put everything into it. And then they're like, now you have to go on the road. Now you have to write articles. Now you have to go talk to people. Now you have to make all these decisions about the cover or the title or release date. All the stuff that goes into creative work and then and then probably like the third marathon is just like and now you wait like now because it never happens as soon as you want like i started my first blog in 2006
Starting point is 00:05:40 i sold my first book 2011 wow my first new my the and then my first book in 2011. Wow. My first new... And then my first book about philosophy, The Obstacle is the Way, came out in 2014 and it didn't hit a bestseller list until 2019. Crazy. So it's on top of all that, then you just have to... Master your craft or acquire a skill and become really great at it. Then learn how to promote and market it and get it out there in the world. Then wait another five to 10 years for it to actually get the results you want it to get. Yeah. It's like, it's like investing. Like
Starting point is 00:06:14 first you have to make capital, like earn wages. You have capital. Then you have to find the opportunity, the thing you invest in. Then you have to wait. To wait five, 10 years till you make some money. Yeah. Compounding returns, interest., then you have to wait. To wait five, 10 years till you make some money. Yeah. Compounding returns, interest. You just have to let time do its work. And I don't know if you're like me, 10 years ago, I invested in a lot of things that never made money, that I lost all the money. So you have to make a lot of mistakes through the lessons of promoting marketing or putting yourself out in the second marathon. Yeah.
Starting point is 00:06:41 In the third marathon of just waiting around for time to pass. And then what if your thing is like really ahead of its time, right? Then you have to wait even longer. They don't care. So yeah, you have to wait longer. I kind of feel like Masking Masculinity for me was a little ahead of its time. It came out like right when Me Too was happening and they're like, oh, we don't want to listen to a guy talking about vulnerability. We just want to yell at men or expose the men who have actually done the really hard things, the really bad things. And men weren't looking to find the answers or seek within. And so now I see it happening like a second wave four years later where people are
Starting point is 00:07:17 like finding it, buying it, sharing it. They're like, wow, this is really powerful to understand this. Well, there's this expression that nothing is more powerful than an idea whose time has come. And so the difference I found, yeah, like you work really hard, you make something, it's objectively good, but then timing is not perfectly right. It doesn't fail. It's like a single, but then we have something and it's exactly time to the moment, then it's a home run, or your thing is just kind of floating there waiting for the moment. So like I saw this during the, I've been writing about stoicism and so resiliency and obstacles and also stillness these things they they worked but then you know march 2020 they take on a different relevance to people and six years ago they weren't as powerful yeah and now also suddenly people have time right and so to do a
Starting point is 00:08:04 daily meditation. Yeah. So then it's like, then, yeah, you can either get a second life or a third life. And so I think the important part is like, you do the work, you put yourself out there, you have to trust that it's going to work. Sometimes it does, sometimes it doesn't. But yeah, it's a grind. I have a thesis that if you want to overcome your fears, you have to go all in on it. I don't think you can outthink your fear.
Starting point is 00:08:30 You have to go all in on your fear in order for the fear to start to disappear. Okay. And you've got to have a lot of courage in order to face the thing that you're insecure about, that you're afraid of, people judging you, that you're afraid of failing or falling down on your face. But once you overcome it, or at least you're able to face it in a comfortable stance, maybe you're never fully comfortable, but at least you're like, I can do the thing. That's when I feel like your greatest gift can come to the world. Or that's where I feel like there's so much reward on the other side. But it's extremely scary to face our fears. Why do you think it's so hard for people to face their insecurities, their shame, their fears, their
Starting point is 00:09:12 doubts? Well, if it wasn't scary, then like courage wouldn't need to be there. So like, it's good that you're afraid, right? Like if, I guess one way to think about it is like, if there wasn't a risk, let's say it's starting a business. If like, all you had to do was like have an idea for business and then it was guaranteed that you'd be successful, then everyone, there'd be a lot more businesses, right? Like everyone would do it. It's so the fact that it's scary is partly what makes it valuable because most people are not going to get over the fear. So when you think about things that are scary or challenging, you could think about it like a heavy weight. If the weight is easy to lift, you're not going to build any muscle.
Starting point is 00:09:54 So that you have that sensation of fear or hesitation or doubt, one way to think about it is that it's a positive sign. Like Steven Pressfield talks about that the resistance you feel is commensurate with, like, the value. So, like, you're not afraid to do things that don't matter. You're only afraid to do, like, big things that matter. So the harder or the scarier it is, the more valuable that thing is for you sometimes? I think I would say a lot of the times, not all the time. Maybe it's scary because you're about to implode
Starting point is 00:10:27 or drive off a cliff for no reason. It's not that fear has no place, but it could be a sign that you're on the cusp of something. And so when I think about it, I go like, okay, if I'm not pushing myself, if I'm not scared,
Starting point is 00:10:43 that's probably a sign that I'm just doing something that I'm already really comfortable with and therefore not growing. So I think it's good. It's a good sign. But I think the reason it's scary, you said you can't like outthink it. I don't know. I disagree a little bit. What I would say is that oftentimes the reason we're scared about it is because we haven't really thought about it. So we have these kind of like vague fears, you know, like, well, I don't want to do it because. And then you're like, because why?
Starting point is 00:11:15 Like, tell me what you're really thinking. The worst thing that will happen because I got made fun of because I get my money. It's actually not that big a deal. I talk in the book. There's a story about Pericles. He's this great Athenian general. And he's leading these troops in a naval convoy and there's this that suddenly like there's an eclipse and like imagine living eclipse yeah thousands of years ago you don't know what an eclipse is just all of a sudden the middle of the day right and so everyone's scared and they thought is this like an omen is Is this the gods? Are they angry?
Starting point is 00:11:48 And there's a similar story where like thunder happens. And they're like, what is that noise? What's going on? And he just goes like, so it's plunged into darkness. And he grabs his cloak and he puts it over this guy's head. And he goes like, are you scared of this? The guy goes, no. And he's like, but it's just darkness. He's like, what does it matter if the darkness is because the
Starting point is 00:12:05 sun disappears or because like i put you know my cloak over your head so i think some of the times we're scared because we haven't really thought about what it is and so it's kind of this enormous boogeyman that if we actually took a minute and we broke it down and we thought about it it wouldn't be as scary as it was. So I agree that you want to go head on, but part of head on is just like, what am I actually afraid of here? Like, what is this? And oh, it's not nearly as big as you think it is. I hear you there. For me, I guess the thing that I'm thinking of is like, when I was a teenager, I was terrified of talking to girls. Sure.
Starting point is 00:12:46 And I wasn't able to outthink it and be like, okay, they're just going to laugh at you and then you're going to be fine. I almost needed to like experience it and realize physically I'm okay. Yeah. Same thing with salsa dancing. I was like fascinated by watching salsa dancers, but I was terrified to get laughed at. Sure. And to look like out of place and not in the right cultural fit. laughed at. Sure. And to look like out of place and not in the right cultural fit. And for months,
Starting point is 00:13:12 I was paralyzed with the idea of like looking silly, making someone else look bad, getting laughed at, not fitting in, not belonging, all these things, just not understanding the language of salsa dancing. And finally, I did it for the first time in the middle of, I don't know, probably a hundred dancers. And I was shaking, trembling, terrified. And I remember after about 10 minutes, I looked up and no one cared. No one was watching me. No one's looking at me, but I don't think that I've been to outthink it because the fear was in my body. And it was almost like I needed to physically do the action and feel it until I was like, okay, I'm still not comfortable in this situation, but like Batman, he had to live in the cave. He didn't just say, well, let me just think I'm a bat.
Starting point is 00:13:51 He was like, I need to become the bat. I need to live with the bats and let them swarm around me and realize I'm not that afraid, or it's okay. I can learn to embrace this discomfort as opposed to outthink the fear. I remember one time I was sitting in a cafe on Houston Street and you walked by and you- In New York?
Starting point is 00:14:09 Yeah, it was like, it had like a glass of wine and all of a sudden I heard this knocking on the store. It was you. Yeah. And you were like, hey, I'm going salsa dancing. You wanna come? And I just remember thinking like, I would literally rather die than do that
Starting point is 00:14:20 because that's the same thing. It's terrifying. But I do think physically experiencing it can be really valuable because you realize yeah it wasn't what you thought it was but it is interesting so like you you're afraid of salsa dancing tiger girls at the same time you were playing football at an elite level you were going up for passes getting smacked by someone running full like you could literally still scary though i mean you could literally die yes like you could literally. It's still scary though. You could literally die. Like you were not afraid to be hit basically by like a car.
Starting point is 00:14:50 Right. And yet you were scared of what people thought. So it's like, it's funny because we think that when we think about courage, we tend to think of physical courage as being like the end all be all. I almost feel like it's easier to run into a building that's on fire than it is to like go up
Starting point is 00:15:04 and talk to your crush when you're like terrified of the rejection because maybe physical instincts would be like i'm gonna go rescue this person out of a car out of a crash like i would just get up and go but i would be like as a teenager this girl's gonna laugh at me and all my friends are gonna laugh at me and i'm not gonna be accepted and no one's gonna love me and i'm not going to be accepted and no one's going to love me and I'm going to die alone. Well, there's war heroes that run for political office that then are afraid to vote against their party because people will be mad at them or they could lose their job. So different types of courage, right? Yeah. So we often think of physical courage as the end all be all, but I would actually argue that moral courage is hardest and more rare. And the tricky thing is that people will have one and not the other.
Starting point is 00:15:48 And it could go in either direction. But that's really the tricky thing. What has been the hardest, before you wrote this book, because I feel like every book you write, there's always something in you of like, I've got to write this because I know I haven't been fully mastered this thing yet. Of course. So where were you lacking courage in your life before or during writing this book? Was there parts, or maybe it was years ago that you've mastered now, but what was the thing maybe that was the hardest for you to have courage around?
Starting point is 00:16:16 So, I mean, I've gone through scary things in my life, whether it was dropping out of college, the decision to leave the corporate world to become a writer. These are all scary things. And even the decision to go from the marketing track i was on to writing books about an obscure school of ancient philosophy like that was you know i took a major uh hit in the advances you know it didn't work right away i you know i was worried whether people were gonna like it or not but i do one of the last stories in the book i talk about when i was at american apparel and i think one of the scariest things that people face is like if i do this i could lose my job
Starting point is 00:16:53 right even though this might be a job they're thinking about quitting like at that very moment there's some we had this huge mental block between quitting and being fired right um and i was thinking the story i tell is i was thinking about leaving american apparel to become a writer and then i get asked to do this sort of unethical thing at work and i say i'm not going to do it i don't do it but that was as far as i took it i didn't want to stop like i i didn't want to go toe to toe to stop it from happening right and you just did it said i'm not going to do this but you knew it was still happening i said that's a bad idea i'm not going to do it find somebody else and i but i could have said like that's not right don't do that right and i didn't have to watch as it happened. And I think back, I go, why?
Starting point is 00:17:46 And it was like, well, you didn't want to lose your job. Right. A job that I left shortly thereafter anyway. And I think what I think about in retrospect is like, why did I want to keep a job that you could get fired from for doing the right thing? And so when we, I think it's, the reason I tell the story
Starting point is 00:18:07 is that I wanted to make an important point, which is the excuse, I was worried about X or I was afraid of Y does not age well. Like when you look back, you're never glad that you chickened out. Like you never are. That's the truth.
Starting point is 00:18:26 And so, yeah, I think I don't want the book to come across as like, you know, I'm super brave. This is my story. The story is, the book is here are inspiring people throughout history whose courage is calling to us to be better. And like, I actually end the book, not with a story of courage, but a story of sort of a failure of courage. Because I think that's really like it's funny if you should be afraid of anything, it should be afraid of like you should be afraid of betraying your principles of falling short. Absolutely. Of not doing what you know is the right but hard thing at the time. How does someone develop their principles or their values if they're not clear on them? Or if they were taught different values by their parents, by society, by friends,
Starting point is 00:19:15 in high school, college, how do they get clear on those core things? I mean, I think you develop them as you go. And that's why you can't be too hard on yourself when you fall short, because that's one of the ways you are learning. That's how you learn, yeah. hard on yourself when you fall short because that's one of the ways you are learning. That's how you learn. Yeah. By being a coward.
Starting point is 00:19:28 Yes. Because by making the mistake of being a coward, you learn through pain. Yes. You should have done it differently. And you learn, oh, like the self-preservation that you were following, it's not a guarantee anyway. You know what I mean? Like you're like, oh I don't wanna mess this up, I don't wanna piss off this or that, and it's like, you're assuming that it's yours anyway,
Starting point is 00:19:55 that you have control of it, and you don't. And so it's kind of like, the Stoics talk about memento mori, right? One of the benefits of memento mori is like, actually life is too short to try to hang on to it too tight anyway. Yeah. But I think you develop your compass. One of the ways I think you do it is like, who are your heroes?
Starting point is 00:20:15 Like, who do you look up to? The models, yeah. What would they do in this situation? What is the code that they lived by? That could be your grandparents. It could be your spouse. It could be Jesus. It could be Marcus Aurelius, it could be anyone from history. It could be a character from your favorite book. What would they do? I think that's a really key
Starting point is 00:20:35 way to do it. Interesting. But this book and then the series of books is built around what's called the cardinal virtues, which are actually the virtues in Christianity, in Stoicism, actually appear in a bunch of different philosophical schools. But the idea is courage, self-discipline, justice, wisdom.
Starting point is 00:20:55 So to me, that's kind of what I, those are the principles that I try to live by. And I think every situation that we face calls for one or all of those things. Where do you think people lack courage the most? In what parts of their life? Is it in just being honest with themselves? Is it in how they lie to other people?
Starting point is 00:21:18 Is it in how they don't stand up for what's right? Or at least what they believe is right. Is it physical courage emotional courage you know i think it's all of the above and and and i think it's important it's like no one is like fully brave or fully a coward right like it's more like day in and day out what do you do right but i think one of the places we struggle with the most is like if courage is rare, courage in pursuit of the right thing is rare still. So the virtues are interrelated, right? Like one of the stories I tell in the book is, okay, think about Michael Jordan, the decision for Michael Jordan to walk
Starting point is 00:21:59 away from basketball. And play baseball. Immense courage, right? Think of the amount of people who told us a bad idea, told him he couldn't make it, wasn't going to work. I think of the money he left aside, right? Real courage. But contrast that with Maya Moore leaving equally dominant in the WNBA. She leaves at the height of her career, not to go play a different sport, not to go on some spiritual pursuit, not to go on some spiritual pursuit, not to, you know, spend time with their family, but to free a man wrongly convicted who's spending his life in jail. So courage is important, right? The courage to like, oh, I'm going to quit my job and start a company. Great. Very courageous. But the person who quits a job to dedicate themselves to some meaningful cause
Starting point is 00:22:45 that's to me the level above uh i and i so i think it's it's courage but courage in pursuit of what right we all know people who are savvy investors they're great at taking risk managing risk they're bold they're making cool but is it in service of their bank account or is it in service of doing something that matters? Right. Where do you feel like you struggle the most with courage still? I think that's a good example. The story I'm telling is where I continue to struggle. It's really hard to say or do things that you know will have financial or career repercussions for you. Right. Right? So, like, I think early in my career, I was like, oh, I guess I've said this to people.
Starting point is 00:23:45 I was like, happy to be here or happy to be wanted. So I would go like, oh, this is the opportunity. I'm excited, grateful. Let's do it. Not like, does this align with my values? Do I feel like this makes the world a better place? But so it wasn't greed so much that was motivating me, but a fear of what would happen if I said no. So like I often find myself saying yes or not objecting or being like fully articulating what I think and feel.
Starting point is 00:24:18 Because like I don't want to be on the outside or I don't want to rock the boat. Right. So I think what I've been working on is just like, this is what I think, this is what I feel needs to be done. Like come what may, I'm trying to get to a place where that is consistently who I am and what I do. But it's scary because like, first off, what if that's, what if the opportunities dry up because of it, right? And then I think as I've gotten older and you have more responsibilities, you realize it doesn't just affect you. It affects the people who work for you. Your kids, your family. Exactly, exactly.
Starting point is 00:24:57 So people will, you know, people will go along to get along, right? And that's, like, so one of the things that's done is given me some empathy i try to i have a chapter in the book about like basically never question the title of the chapter is never question another man's courage meaning like we'll we watch we're like why are these bums in washington like why is the mayor doing this or like why isn't why isn't lebron james speaking up about you know he's like why is it lebron james speaking up about what's going on in china right and it's like why don't you speak up about what's wrong in your industry right so it's like it's very easy to get in this trap where you're criticizing other people's courage or lack thereof.
Starting point is 00:25:47 Instead of doing what we should be doing, what we should take from these examples is like, what am I putting on the line? You know, what deals am I torching? How am I stepping up? Exactly. Like you, we look at a politician, we go, why won't they vote for this or that? Who cares if they don't get reelected?
Starting point is 00:26:06 And it's like, well, they care. And so it's like, when have you gambled your career? What stands have you taken where you're like, this is unpopular, but I feel morally obligated to do it. And I'm willing to accept the consequences of that. What happens if the consequences are really bad and you are broke for years and you don't have opportunities for years? You know, even if you want to self-start and just no one's, you're just so excommunicated from whatever society or community or families that you are part of that now. Okay, I stood up for what I was courageous, but what did I get for it? My own personal pride and loneliness? I mean-
Starting point is 00:26:47 Well, there's a tension there. So like at American Apparel, so I didn't do that, right? And, but by not doing that- You kept your job. I kept my job, but which didn't just benefit me. I was then later in a position when the company had more leverage over the founder and the owner to actually make it
Starting point is 00:27:09 right in a way that worked, right? So, you know, noble failure, what good is that, right? Like, if you take your stand too early, if you're the person who, like, you and I both have an audience, right? If we had earlier on in our career maybe taken certain stands, that audience wouldn't be there to then talk about whatever the important thing is. The problem, the trap is we say, oh, I'll do it later. I'll do it later. I'm still building. I'm still working.
Starting point is 00:27:41 And then you never do it because now it's actually more expensive. Right. Now we have more to, we think like you, we think like, oh, that guy's a Senator. He should be able to, or this woman's the governor of the third most popular state. Like she should, but actually the hard part is as you get bigger, it's more to lose, right? Like you go, oh, this, this decision could cost me a billion dollars. A lot. Not that I ever have a decision. But actually, it doesn't get easier as you get more successful. It can get harder. So you actually need more courage as you go.
Starting point is 00:28:15 It's easy to be the guy on the sidelines saying how things should go. But then when you have, again, when you have people dependent on you, when you have influence, when you have something you've worked your whole career for, it's scarier. So you need more. So what is something from the Stoics that everyone should learn right now to help them have more courage and live a greater life? If there are three things that everyone could take away from the Stoics to improve the quality of their life right now, first, what would that be? I got some good ones.
Starting point is 00:28:48 So one of the questions we ask ourselves when we're like afraid of something, when we're thinking about, we go, but what about me? What would I do if, right? Like we're worried. And Marcus Aurelius goes, you'll meet that with the same weapons you've met all your other problems. So remembering that like, hey, you've been all your other problems. So remembering that like, hey, you've been scared before and you're still here, right? So we often, often what our fear is
Starting point is 00:29:11 really doing is underestimating or undercounting how good we actually are at what we do. Like you're not, you're, you're not suddenly tomorrow going to be a helpless loser. You're the same person you are today. And what will you do? You'll figure it out. Just like if you quit your job, you'd be like, I'm quitting and I'm going to go find a new job. But if you got fired, that suddenly feels like disempowered, whereas the other one feels very empowered. So remembering what you're capable of, to me, is really important. Okay, that's good.
Starting point is 00:29:43 So remembering what you're capable of, to me, is really important. Okay, that's one. Number two, the Stoics say that we should always be training. So one of the reasons I think it's important to have, like, a physical practice, one of the reasons it's good to seek out adversity and difficulty is so when stuff happens, you're ready. Epictetus, one of the early Stoics, he's actually a slave. And he says, like, you want to get to a point where when stuff happens, you're able to say, like, this is what I trained for. Right. Like, you knew this could happen. Man. And you did the work.
Starting point is 00:30:20 Yes. Before you go into the next one, it's right when the pandemic happened, I was like, this sucks. And yet I've been training for this for the last like 12, 13 years of my life. Yes. Because in 2008, when I, well, in 2007, I got injured and had surgery. And then 2008, the housing crisis, and there were no jobs for someone like me without a college degree that was ignorant from school. I was like, I better develop myself so that when this happens again in five, 10, 20 years, I'm ready to take on any adversity. Maybe it's not fun and it's still challenging, but I'm prepared and ready. And I spent 13 years training for that moment. And I felt a sense of, kind of weirdly, I felt a sense of peace that gave me the energy and the clarity to take action and shift where I needed to. And lead from a place of courage as opposed to, and I wasn't perfect, but lead from a more calm, peaceful place as
Starting point is 00:31:10 opposed to frantic, fearful place. Well, look, preparation makes you brave, right? You prepared so you were ready. And then I think also because you remembered what you felt then, you were also in a position to lead and understand what people who were not as prepared needed to hear. Yeah, what they're experiencing. It sucks. So you can have empathy like you talked about. You can connect with people in that way. Okay, so always be training, always be learning something new, training yourself physically, mentally, emotionally. And the third one would be this stoic exercise of memento mori, which basically means remember you will die. I actually carry a coin in my pocket that says this.
Starting point is 00:31:51 But I think when you realize like, hey, life is already short and fragile. Like I don't need to, if I'm spending my time cowering in fear or worrying, I'm acting as if I have a certain power over things that I don't. There's this famous Stoic story where, like, the emperor sees this Stoic philosopher he hates, and he's like, I'm threatening you to death, or I'm sentencing you to death. And he's like, I was already sentenced to death. At some point.
Starting point is 00:32:22 Yeah. He's like, you have no more power over me than I had, than life itself has. Than Mother Nature. Yeah, just me dying. And so realizing that life is fragile. I think sometimes people can miss this. Like, memento mori doesn't mean like, oh, like, don't wear a motorcycle helmet or pretend the pandemic is not real. That's not what it's saying.
Starting point is 00:32:44 the pandemic is not real. That's not what it's saying. But it's saying like, hey, focus on the parts of safety and concern that are in your control. But if you're wasting your time being afraid, that's something I thought a lot about in the pandemic. It's like, look, I don't know, especially early on, we don't know where this is going. Don't know what it means. Don't know what is ticking clock is in anyone's body, right? What pre-existing condition you might have or bad piece of luck you got. So you take it seriously. But within that, what are you doing with your time, right? Like, what are you going to spend your time on? So if you're spending that time worrying, stressing, watching the news all day. Yeah, what you're actually doing is rejecting the life that you have
Starting point is 00:33:29 in front of you at this moment. It's kind of like a longer eclipse. It's like there's an eclipse that's happening. We don't know what this is, but you can sit there and worry and fear for those five minutes of your eclipse or whatever, or you can look up and enjoy it and do something with your time
Starting point is 00:33:45 and make the most of this and prepare and strategize and organize your time. Yeah, James Stockdale, who spent seven years in a prison camp in Vietnam, who reads the Stoics, he says, you know, he gets there and he goes, I never lost sight of the fact that I controlled the end of the story.
Starting point is 00:34:06 Right. So if he got out, that he would control the end. He would decide what he said and that I could turn this into something that in retrospect I would not have traded for. Isn't that crazy? That's incredible. It's like Mandela as well. It's like 25 years or something. 25 years or something. So I think we have, it takes courage to say, this thing happened to me and I wouldn't have chosen it. I didn't want it. But now that it's here, I'm going to face it.
Starting point is 00:34:34 I'm going to apply all my training and experience towards it. And then I'm not going to waste my life being bitter, resentful, afraid, passive about it. And I'm just going to get to work turning it into something. Yeah. I'm not sure if this is 100% true or accurate, but I heard someone say that Bhutan is like the happiest country. Really? I'm not sure if you've heard of this. It's because, I don't know if everyone does this or just some people do this, they focus on their death five times a day.
Starting point is 00:35:07 Interesting. They think about their death five times a day. And so there's an app, I think it's called Croaked. Yes, I've seen this. Or You Will Croak or something like that, where five times a day, I had it for a while, it sends you a reminder you're going to die with an inspiring quote that has you reflect on your death five times a day to remind yourself.
Starting point is 00:35:27 Do you have this on your phone? No, no. Did I give you one of these? This is what I carry in my pocket. Let me see. Oh, nice. You should just carry that. It's like a nice weight.
Starting point is 00:35:34 So I spin it. And the idea is- You could leave life right now. And the rest of that quote, so Mark Sweeney says, you could leave life right now. And then he says, let that determine what you do and say and think and so that so to me the the power of meditating
Starting point is 00:35:51 on your death is that it puts everything in perspective right um it doesn't make things meaningless it actually makes them meaningful because in it says like if this doesn't matter i shouldn't be doing it and if it does matter i should be doing it as if it is the last time that you get to do it right like i think one of the things i don't know about you but like as like an ambitious or driven person i find myself like rushing a lot right like like gotta go gotta go there, this is taking too long, I don't wanna wait. I even found myself, like my son, he often like naps in the car. So it's like, you're in the car as long as he's asleep.
Starting point is 00:36:35 And I'll find myself like you're behind a slow driver, and you're like, I gotta get around this. And then I'm like, but I'm not going anywhere, right? Like I'm rushing. And so what I've started to remind myself is like, what are you rushing towards? You're rushing going anywhere, right? Like I'm rushing. And so what I've started to remind myself is like, what are you rushing towards? You're rushing towards death, right? Not just because speeding isn't safe,
Starting point is 00:36:51 but you're rushing towards, like as you're rushing out of a moment, you're rushing away from life. Seneca talks about, he says, don't think of death as happening in the future. Think of death as happening right now. Really, why? The time, he says says because the time that passes belongs to death Right like so when you when you die, you're like you've lived 80 years, but you also that's 80 dead years
Starting point is 00:37:15 That can never come back So if you think about the time that passing as being death happening like you're every minute you're getting closer to death passing as being death happening. Like every minute you're getting closer to death. You don't want to rush through a moment. You want to fully experience the moment. Even if you're waiting in line or behind a car or impatient. This is life. And when you're rushing, you're rushing away from it or you're rushing toward death. And so you slow down and you go, okay, I've been alive 34 years. And so you slow down you go, okay. I've been alive 34 years Why do I have to like did I was I alive for 34 years or was I rushing right? Or was I rushing away to to get to 35, but maybe I die at 35, right? You don't know so so if you if you just go like the present is here
Starting point is 00:37:58 I'm gonna be controlled enough and courageous enough to just This is enough. This is it doesn't need to be anything or anywhere else i'm just going to be here and i'm not going to rush away and i kids have really been helpful for this because you're like oh not only am i rushing potentially like towards death but you're at the very least they will never be this age again. So as you're trying to, as you're trying to get this over with, you, you, you have to intellectually.
Starting point is 00:38:29 You miss those years. Yeah. And eventually you're going to, you'll be like, oh, if only they were five again. Right? Like,
Starting point is 00:38:35 you know, but you, when they were five, you wanted it to be over. And so. The screaming, the crying, the pooping or whatever it is.
Starting point is 00:38:43 It's like, oh, I wish they could do this on their own. But you look back and you don't really want that. Yeah. So I want them to stay there forever. You're like, of course, but it captures this moment. Yeah. And this is true even for the shitty stuff. Like even when you're stuck in traffic, even when you're home with the flu, even like.
Starting point is 00:39:02 So true. It's like I don't know if you think about this. I mean, you've always just been like talented and successful your entire life. Unlike me, where I struggled and went through pain for years. But I feel like, especially the years after my dream was over playing football and I was like, well, who am I?
Starting point is 00:39:19 What is my identity? What is the value I add to the world if this was my value? How can I just survive and thrive in this world without that value or identity anymore? I remember just being in a state of uncertainty for a while and wanting to get out of it, wanting to have a job, wanting to launch a business, wanting to have money, wanting to have an audience, wanting to have a book, all these different things, wanting to have something. And when I look back and I'm like, man, those moments were really meaningful of what I was living and
Starting point is 00:39:52 learning moment day by day, the struggle, the pain, the adversity. I'm recreating that in other ways just by trying to get to the next level, but I'll never live that aspect, those moments again, the specific time. And when you got those things, was it as magical as you thought it would be? It never is. Yeah, I mean, it wasn't as fulfilling. It was cool to see like a full circle and reflect back, but it was never like, oh, this is, I've made it, you know?
Starting point is 00:40:19 You never feel like you've made it. And so that, like, I talk about this a little bit in some of my stuff where, like, what will happen is you get to the medal stand, right? New York Times bestseller, Olympic gold medal, you know, All-American, whatever the thing is, right? And there's an anticlimactic-ness to it. Very.
Starting point is 00:40:41 After 10 minutes, you're like, now what? You talk about this in the School of Grades. You're like, now what? So the problem is people can learn, you're like, now what? You talk about this in the school of grades. You're like, now what? So the problem is people can learn. You can go two ways. You feel the now what. So you can go, now, oh, I've got to find something really meaningful. I've got to go bigger.
Starting point is 00:40:53 Well, no, no. So either you look at that and you're like, oh, it was never about accomplishments. It was always about being present and meaning and connection and the friends you made along the way. Right, right. Or you go, oh, it's that I have to do it again. Or, oh, it wasn't a million dollars. It was a billion dollars. Yeah, yeah.
Starting point is 00:41:13 And so you can see why that moving in the goalposts creates really successful people. But they are rarely happy people. Happy or fulfilled. Yes. Or peaceful inside. Yes. Or peaceful inside. Yes. And I think it's the journey I'm on, what I'm trying to do,
Starting point is 00:41:30 I would like to be proof that it is possible to be world-class at what you do and come from a place of contentment and fullness, not have to do, not being like, I just need this, then I will be good. Because you're never, ever good. There's always going to be some writer better than you or someone that writes a book in a way that's different than you or some, whatever.
Starting point is 00:41:53 There's going to be someone more talented, more successful, richer. Of course. I mean, you meet someone, there's a story about Joseph Heller and Kurt Vonnegut. Kurt Vonnegut wrote slaughterhouse five joseph heller wrote catch 22 two of the great writers of the 20th century and they're at this party and you've been at parties like this where like you're at a much richer person right like like one of those you're like why am i here and and kurt vonnegut is teasing joseph heller and he says like you know this guy made more money this week than your book will make
Starting point is 00:42:26 in its entire life. And he says, yeah, but I have something he doesn't have. And he's like, what could that possibly be? And he says, I have enough. Ooh. And it's not that that guy just wrote Catch-22 and then he sat on his ass. He wrote other
Starting point is 00:42:42 great stuff. He did great work. He just wasn't coming at it from a place of craving. Like, you know, we have that word thirst. Like he wasn't thirsty. He was quenched, but he was doing it because he actually liked it. I remember the first time one of my books hit number one, I was mowing the lawn at my house
Starting point is 00:43:02 and my agent, Steve, called me and I was like, now I have to finish mowing the lawn at my house and my agent steve called me and i was like now i have to finish mowing this lawn you know like it was like okay at a 10 minute moment yeah still here like pushing this thing and then you realize like oh it's never gonna be i don't know what i thought it was gonna be but i didn't think it was gonna be that and i feel grateful that i didn't think oh i have to have back-to-back number ones that will be it you know it's interesting i remember steve when steve called me because we're the same agent and when i hit number i didn't hit number one but i went hit the new york times bestseller list and i remember for like an hour just being like wow this is something i dreamed about but then after an hour like calling
Starting point is 00:43:40 everyone and like congratulations i was like did anything change? Like nothing really changed. I accomplished a- Don't throw your parade. Yeah, there wasn't like opening up the gates and money dropping down or people calling me. It's like a few people noticed and a few, okay, you do one post on Instagram and then people compliment and then people move on.
Starting point is 00:43:58 And time moves on, you know, it's- On this book, I'm actually thinking about that because you know, when you do a book, there's this whole lane of prioritization of like, how do you get on the list? Yes. And it takes a lot of your time and energy. Man. And why do you do it?
Starting point is 00:44:11 It's obviously there's some business reasons, but part of it is, if not ego, it's this like people said that's important. So you're like, that's as good a target as any. On this one, and I'm a little bit of a thing with my publisher where I'm like, no, I just want to like get as many books in people's hands as possible so i'm like ignoring all that but there is a kind of a fear there because it's like the one benefit of that strategy is that the success is clear and objective and recognizable by other people yes so like the book's going to come out i i know it's doing well i already know the track that it's on but like i'm not saying i'm gonna get condolences but there are people are gonna be like oh i guess it didn't work as well you know like so so it's kind of been like all your books they like didn't hit right away it's
Starting point is 00:44:53 like two years later now it's number one but and it's crushing just the idea of like hey i you have to determine what success is to you and to not base it on what other people. That's so hard. That's courage. It's hard to do that. I'll tell you what. For me, the last two years, I've been working on developing a new book. But I've also been like, gosh, do I do the traditional publisher thing? And I've been having these conversations.
Starting point is 00:45:18 But I'm like, I just want to let that go and just write a good book that people are impacted by. Right. But it's like, oh, do you worry about the advance and what people are going to ask you about it? Or do you not care about that at all? Yeah. Self-publish it and just try to help as many people as possible. Is there a balance? And literally, it has been holding me back until the last, like, six weeks.
Starting point is 00:45:38 The last couple of years, I've been in this limbo. I think, one, because I've been trying to trying to like build my business and the pandemic and shifting. But this has been on my mind, this conversation for two years during all this. And it's not until now where I'm just like, okay, I need to get clear and I just need to take action and do it from the highest level place possible. Do things that are smart as well for business, but also just do what's going to help as many people. Well, it's a safety net, right?
Starting point is 00:46:05 To do the conventional, like, this is how it's done is safer. Because, like, then no one's going to be like, what an idiot. Right. Or like. Oh, he's falling off the wagon. Yeah. He's a loser. It didn't work.
Starting point is 00:46:19 You know, he's on the decline. Yeah. And so the decision to, like, do stuff that you care about, that requires sort of like burning the boats behind you and just going like, I'm on this journey. And I think it's particularly hard in today's world where there's view counts and likes. There's so much more public quantification of what's done. And when I talk to sports teams,
Starting point is 00:46:45 I sometimes say that I'm a little bit jealous. It's obvious whether they're doing a good job or not. You're jealous? Of who? I love the clarity of sports. Win, lose. Win, loss. Track and field, yes.
Starting point is 00:46:58 Did you get the height or not? Yes. But the reality is, in the world that the rest of us exist in... It's like a committee, and how many people like it. You're running your own race. You have to decide what success is.
Starting point is 00:47:10 And that means criticizing yourself when you fall short of your own metrics. And it also means congratulating yourself on a success that perhaps other people don't recognize. Right. The success could be just, I'm proud of this chapter I wrote in this week or this month, even though no one's going to see it. No one's like buying this, but I'm proud of the work that I'm putting in, the effort, the energy, the process.
Starting point is 00:47:34 I've tried to get to, I would say that on my first book, I was 10% this is a success because I made it and it was the best I was capable of. And 90%, let's see what the results are like let's see how it does and i would like to think that as i've gone forward that slowly flipped and that i'm now 90 it's already a success because it exists even if no one buys this it's my best work yeah yeah and then 10 like bonus, like, hey, it worked, won awards, got recognition.
Starting point is 00:48:09 But isn't it the, like we talked about in the beginning, there's kind of like three levels to like a book. There's the master of writing the book, which you've become one of the greatest writers of our time and distilling wisdom, ancient wisdom, and creating practical examples on how you can actually do this for today's life. And millions of people have read your books. But you could master writing the book, but you also have to master doing the marketing and promotion and putting yourself out there and communicating it.
Starting point is 00:48:38 And then master being patient. Maybe put out the great book and no one cared about it right now for a few years, but then you'd be patient and people start buying it. Well, I think you want to rank them. So the Stoics say that their first task in life, the most important task in life is what is up to me and what is not up to me. Like separating things into the category of, is it in my control is it not in my control so as i look at like any project or business or whatever i prioritize based on like what's most in my control to what's least in my control so like the first mastery the of the the thing itself like is it
Starting point is 00:49:18 the best album the best video the best you know live event it could possibly be. You have as much control over that as you're going to have of anything because that's yours. So like there you have the ability to get most of the win before it's even out. Then marketing and promotion and communicating and talking about it, that's like more something you have influence over as opposed to something you control, right? Because it's like, what's happening in the world? You know, like how on point or trend is your thing? You know, are you, but it's also, are you willing to put in the time? Are you willing to, so many people just think they're better than that. And so they don't do it. And then the third part is the patience or
Starting point is 00:50:05 the time it's like you got a the audience will like it you imagine your Herman Melville you write Moby Dick it gets savaged everyone's like this is not just not good this is horrible horrible you should be we're offended that you did it and then only like towards the end of your life and after your life does it finally get the recognition you deserve. So that part's the least in your control and you have to be somewhat detached from that. Right.
Starting point is 00:50:33 Because if you're sitting, if you wake up every day and you're like, is this the day that people finally recognize me for all my contributions? You have handed your happiness over to something that's not up to you. It's true. It's funny as you were saying that. I grew up in a religion called Christian science that a woman discovered this religion and wrote a book called Science and Health. And just the
Starting point is 00:50:56 same time back in the late 1800s when Mark Twain was around. And they were kind of like frenemies, I guess. And Mark Twain wrote an entire book trashing this woman, Mary Baker Eddy, and her findings of the science behind healing. It was essentially like the science of Jesus' healing. Here's how it works. Here's how the mind works and how we can heal ourselves. And he wrote an entire book bashing her and the religion called Christian Science, which was like this critical of her work because she kept writing the same book with expanded updates every year, like so many different editions of the same book. And it kept hitting
Starting point is 00:51:38 number one and he had to write new books all the time. So I think he was frustrated that this woman kept writing the same book over and over with like, here's more finding and research and science of how the mind and body is healed through the mind. And it's funny, like she just kept going because she was focused on the work and healing people one at a time and the message spread. But I think it's interesting that, um, for a reason, for a reason that came up for me, because the more you put your work out there, the more criticized it's going to be open to. There's more people that are going to be willing to criticize it. And I think a lot of people aren't ready for criticism. They're not trained to deal. No one teaches you how to deal with criticism when you have an audience.
Starting point is 00:52:21 No, no one teaches, because it's a champagne problem that a lot of people never get to yes so there's not like a lot of instructions but it is inevitable and like you have to realize one i've realized a couple things one is like critics are almost always louder than your fans like people who dislike something are much louder than the people who are like why is that pretty good why is that i think it's one feels more strongly than the other like the stuff i like i'm like cool right you know but then when you really hate something you're like i need them to suffer the how i am suffering so a lot of times i think you're just just different levels of enthusiasm even if you know even if 10 of the people hate it and 90% of the people liked it, you're going to
Starting point is 00:53:07 hear more from the 10%. Yes. How do we prepare ourselves to have courage knowing that criticism will come to us? This is why it's really important to know what you were trying to do or what your success is, what success was. Because a lot of times i will see negative reviews of my work it'll somehow get to me and i try not to i try to like keep it at uh a distance anyway but it always gets yes and sometimes the thing people will be criticizing negatively will be exactly what i they'll be like you know uh there's no original ideas in this book. This is just Ryan popularizing ancient wisdom. And it's like, hey, bro, that's exactly what I was trying to do.
Starting point is 00:53:50 Right, right. Like, you're just saying, like, what is this guy? He has brown hair. It's like, that's it. Yeah, that's what I meant. Like, and it's actually even less than that. I love when people say nothing new here.
Starting point is 00:54:03 Yeah. Like, I mean, there's no original idea here. This is just regurgitated or something. But how many original ideas are there? It's kind of like repackaging and purposing something that you can learn it in a different way and understand it in a different way, right? When in my case, I'm specifically not trying to have my own ideas, but to tell you the best ideas from the past. So you have told me that I have succeeded. You've not like what you think you're criticizing me, but you're really
Starting point is 00:54:31 saying I didn't want what you were selling. Cool. Right. So, so when you have a sense of what you're trying to do, then you're able to integrate the criticism. So if someone instead said, you know, Ryan got stoicism totally wrong for the following reasons. Well, now we're at least in the same universe as far as the intention of the work. So now I can go like, well, is this person right or not? But at least we're aligned. Like, I'm trying to get here. You're mad at me for not being over here. Right. Well, I didn't want to go over there.
Starting point is 00:55:07 So we're just, we just shouldn't be friends, you know? So I think really understanding what you're trying to do is great. And then the third one is just like remembering that it's almost has nothing to do with you. Right. Like the criticism has nothing to do with you. It's something going on with them like
Starting point is 00:55:25 all sometimes you'll get like a nasty email and i just go sometimes i like to reply i hope this made you feel better right and and they'll be like i had no idea you would respond i thought this wasn't a real person you know blah right then you realize like oh this person has a life or they're going through something and they thought they were just shouting into the void and you happen to hear it you know so realizing that like hurt people hurt people you know that this is like this doesn't really have to do with you the way that they're making it seem like it has to do with you can be and just because someone's criticizing you doesn't mean you have to take it in no i think a lot of people take it in and they are so affected by it and impacted by it. And that then holds them back from putting
Starting point is 00:56:08 their work out there and creating more because they're afraid of something penetrating and getting in and then holding on to this anger or criticism of other people. Well, there's an exercise from Marcus Freelance that I think about. It's not specifically about this, but I think we can apply it. He goes like, is a world without shameless people possible? No. He's like, a certain amount of people are going to be this way or that way, right? And he's like, so when you meet one of them, you're not like, what is this? You're like, one out of 100 is this person? Is this the kind of person? I just met one. Makes sense. Mathematically, it makes sense, right? Just like you see a tall
Starting point is 00:56:45 person, a certain percentage of people are tall. You're not like, where is this tall person coming from? So like, was it ever possible that you would please 100% of people 100% of the time? Absolutely not. So when you come across someone that is unhappy with your work, you got to go, this checks out mathematically, right? Like, when you look at a YouTube video, you're like, oh, it did a million views, it did 50,000 upvotes, and a thousand downvotes. You're like, who are these thousand people? You're like 1,000 out of a million. Mathematically, that's pretty good, good. You know, that's actually great. Yes. And so again, just reminding yourself that mathematically a certain amount of people, they're just not,
Starting point is 00:57:32 you're not for them. They're not for you. What do you think the Stoics would think about in terms of the law of attraction, manifesting abundance and self-discipline kind of that category? I think about this a lot because people ask me that question because as stoicism has become popular with self-help stuff there's overlap so the stoics are very here's where they would agree marx really says our life is dyed by the color of our thoughts which i think is a beautiful way of... Dyed. Dyed. Like dyed the color green. Yes. Like if you have positive thoughts,
Starting point is 00:58:09 you will see positive things in the world. If you see everything as nasty and bitter and unfair and crappy, that's what you will see in the world. So our perceptions do color our reality, for sure. But the stoic disciplines are the discipline of perception but the next discipline is the discipline of action perception meaning like how you perceive and look at the
Starting point is 00:58:32 world how you tell yourself what you wish for what you think about but then the next discipline is the discipline of action yes so like i don't i don't think the stoics say like oh if you just see everything positive it will be positive. Right. It's that the positivity sets up the action which can make the positivity real. So I think where I get frustrated with people on manifestation or the law of attraction is this idea of, like, write yourself a check for a million dollars and it will be true. Yeah. Right.
Starting point is 00:59:03 Wait. No. Go do the work, right? So if you want things, like when the Stoics see an opportunity inside of a disaster, they're not just sitting around going, oh, this will solve itself. They have to get to work on that thing. Yeah, I've always seen the law of attraction.
Starting point is 00:59:21 I mean, the word action is in attraction. It's like of taking action to attract what you want. But I think perceiving at first is, I didn't know that was the first principle is perception, perception, action. And the third is will. So like what you endure, what you put up with, um, kind of like your disciplines, your, your willingness to endure hard things, challenges that so much of life is outside of your control, that suffering is inevitable. Um, you know, just, just, just the hard parts of life. Those are the three disciplines. What do the Stoics think about in terms of accumulating wealth? I mean, I don't know what they were accumulating back then, but the riches of the world. So the founder of Stoicism is a merchant named Zeno,
Starting point is 01:00:03 who loses everything in a shipwreck. And he washes up in Athens with nothing. And he walks into a bookstore. When was this? What year is this? Like 300 AD. Okay. Right around the time of the death of Alexander the Great.
Starting point is 01:00:18 So he walks into this bookstore and he hears somebody reading philosophy. He goes, what's this? And it changes his whole life. And he would say later, I made a great fortune when I suffered a shipwreck. Meaning he traded worldly goods for real goods, which is wisdom, happiness, purpose, all of that. But the Stoics were business people and generals and politicians. Seneca is like the second richest man in Rome. What the Stoics said was that money isn't good or bad, that it was an indifferent, not indifference, but an indifferent, meaning it just was. So if you had it, you should use it. If you didn't have it, you weren't deprived of anything.
Starting point is 01:01:05 You just didn't have this thing. Now, obviously the Romans lived in a time where things were much more hierarchical and people had a lot less control and ability to start a business. Right. It wasn't decentralized. It was like classes and hierarchy. Yes, and you inherited certain status and things. So they were a little bit more passive than we are today. But I think the idea that money is a tool. If you have it, you should use it. If you don't have it, you shouldn't spend all your life obsessing about it.
Starting point is 01:01:42 But I like to think of the Stookes as being more or less indifferent to it. So what would be the approach if someone was trying to create more wealth and earn a bunch? I mean, like, you know, I don't have that much money, but I'd like to have a more comfortable or financially abundant life where I'm not stressing about money.
Starting point is 01:02:01 Maybe I'm not going to be a billionaire, but... Well, I think that's the problem. A lot of people think of money as this independent good. So they will suffer in life to potentially have lots of money in the future. Right. That, by the way, the Stoics say isn't guaranteed. Right. And you can lose it too. You can't take it with you when you die. Right. And so often people will trade time for money, a priceless resource for a less valuable resource. Interesting. And so Seneca talks about how, like, if your neighbor stole money from you or, you know, built their property onto your property, you'd be very upset. But if they wasted your time, you'd be like, oh, whatever, this is what they do.
Starting point is 01:02:48 Right. So I think also, though, the Stoics would go, what is your actual most valuable resource? It's time. It's your independence of mind. It's your autonomy. So I think sometimes, especially people who are like really frugal, which the Stoics were humble and didn't care a lot about fancy things. I think you can get to a place where you're often valuing money more than it's actually worth. Like you're trading your happiness to accumulate this thing that isn't going to give you what you think it's going to give you. Right. I mean, you're a guy who's driven and successful and wants to keep creating. You've got a nice ranch. You've got cattle and geese and horses and whatever you have on your farm.
Starting point is 01:03:35 You've got family. You've got a bookstore now, a thriving bookstore. You've got all these businesses and you're a team. So obviously money is in your life. You want to have it to sustain a lifestyle. What is your thought process, whether it be on a daily or maybe quarterly or yearly basis of like, okay, do you think I want to reach this financial goal this year? And then how do you approach making money in terms of a philosophical point of view in your daily practices? I will say like as an artist, one of the things I one of the ways I thought about money that's been helpful to me is I want I didn't come from money.
Starting point is 01:04:16 I didn't inherit money. And so I'm not like independently wealthy, but I want to invest and save and earn in a way where I can make the choices I want to make independent of money. So because I had a corporate job and because I was successful as a marketer and I kept my needs minimal, I was in a position in 2012, 13, when I sold my first philosophy book, The Obstacle is the Way. I said, so I just sold, I just done Trust Me, I'm Lying, which was a bestseller. I'd done this little book called Growth Hacker Marketing. So basically did two marketing books. I said, I have this idea for a book about an obscure school of ancient philosophy.
Starting point is 01:05:01 And my publisher offered me half what I got for my first book. So if I had been, let's say financially irresponsible, or I was primarily valuing money as like success, I would have not been able to accept that. But because I was in a place where I'd saved, I'd invested, I had multiple revenue streams,
Starting point is 01:05:28 and I didn't drive an Aston Martin, you know, I was able to go, whatever. Like, that's the book I want to write. So it doesn't really matter what you think it's worth. I know what it'll be worth in the long term. And so I, as I've- So how do you think about that now then? I think about like, I want to create revenue streams or investments that allow me to do what I want creatively, personally, and professionally, and not have to think like, where does the money come from? Right? And I think you and I both know people who are extremely wealthy, who don't actually have that freedom because their lifestyle is at X.
Starting point is 01:06:14 Or, you know, like there's two ways to be rich, right? It's that one is to have lots and lots of money and the other is to like not need lots and lots of money. You know? And so if you can kind of split that difference, I feel like you're in a great spot. Like you're talented. You demand to be paid what you're worth. You know, you invest intelligently.
Starting point is 01:06:34 You are creative. You work hard. And like what you need to feel good is, you know, attainable. Then you have freedom. Like To me, success is autonomy. So if making lots of money makes me feel less free, like I got to keep all this thing going, then I feel like I'm becoming less successful. If I'm at a place where I'm like, this is what I want to do, and I'm able to do it, I'm like, that's good. Right. What would the Stoics be investing in these days? That's a good question.
Starting point is 01:07:09 If the Stoics were around today, where would they put their money? To help their money work for them so they could have this lifestyle of autonomy, freedom, peace, flexibility, creativity, abundance. Would they be investing in crypto? Would it be back in their own business? Would it be real estate? Would it be, I don't know, something more safe? I think it's really hard to answer that because the Roman world was so different. I mean, this is a world where slaves are doing most of the work and, you know, it's a colonial empire that's like pillaging all
Starting point is 01:07:40 these different... It wasn't a good place in good place and they're just stealing and yeah yeah but but i think the i to me the idea of the the best investment i ever made was the decision to move to a little bit of property outside of a big city why is that um so in 2015 i bought a small farm outside austin and you were living in Austin. I was living in Austin. Near town. In town, yeah. You came to my house once.
Starting point is 01:08:09 You saw my goats. The goats. And we need more space for the goats. Yeah, they can't run around enough yet. So we moved. We bought about 20 acres, and now it's about 40 acres right now. Wow, that's cool. About 30 minutes from Austin.
Starting point is 01:08:21 But it was the best investment. I'll give you a couple reasons. One, it's a quiet place for me to write that I'm not looking around what other people are doing. I'm not distracted. There's not a million things to do. It's quiet and it's a little bit apart. If I need to do something, I can, but I'm not like right in the thick of it. Number two, easy access to outdoors, like being outside, being in nature, doing stuff as opposed to, you know, sitting in, you know, rooms all the time. That's really important. And then, you know, the pandemic happens and all of a sudden, you know, my friends who had great apartments in the city are like, I can't do this. Whereas we were like, this is amazing.
Starting point is 01:09:06 Right. We're set up for years. Yeah. And, and we got food here. We got to like, we could hunt. But like, you know, every morning I take my kids for a walk on a dirt road. Every evening we take the same walk on the dirt road. We're outside, we have space. So I think, but that's what it was for me. I'm not saying that needs, but I would say like find where you're happy, like what your place needs to be. And that, I think one of the reasons a lot of people I know have moved in the last 18 months is since they were finally home for an extended period of time, they realized they hated their house or they hated the city they were in.
Starting point is 01:09:49 And they were only there for career reasons or financial reasons or scene reasons. And life is too short to live somewhere that does not make you happy. You say scene reasons, is that what you said? Scene. Yeah, being in the scene. This is the scene, this is where the parties are, I want to get invited to stuff.
Starting point is 01:10:08 And that's just not a good reason to live somewhere. Right. Where should you live? Somewhere that makes you happy? Yes. Somewhere that makes you happy, somewhere that gets the best work out of you. So I write better out there than I do in other places. And so knowing what your space is, than I do in other places. And so knowing like what your space is
Starting point is 01:10:26 and then investing in that space. So that's something I've struggled with too. You asked like, what do you do with money? I think it's like, how are you investing in- Your environment. Your environment, just like LeBron James spends a million bucks a year on his body. Like, what are you investing in?
Starting point is 01:10:41 Like I was for a long time, I was like like all i need is like a laptop and like i'll grind it out you know and it's like by couches and be fine yeah and part of the reason we we opened this bookstore was like i was like i'm gonna kit out like my space like all my stuff's gonna be in one spot i'm gonna have all the technology I need. That was an investment that was well worth it. And so sometimes it's like we cheap out on the stuff that actually lets us do what we do. And if you're not going to spend your money on the thing you do for a living, what are you spending it on? That's a good point.
Starting point is 01:11:29 So they would invest in their environment, their space. I think so. They wouldn't invest in crypto. I mean, I don't know. Who knows? Maybe they would. I'm sure they would invest. Or NFTs. I'm sure they would invest in whatever they thought was a good investment. Yes.
Starting point is 01:11:40 So I don't want to make a pronounce. Right, right, right. Although I'm interested in all those things, I don't want to use this ancient philosophy, which is about, you know, self-actualization to apply so specifically to, you know, this or that, because I think it's more timeless than that. But I think they would be investing in what allowed them to do what was important to them. How would they use self-discipline in all of this as well? Well, self-discipline and courage are interrelated, right? Because too much courage, Aristotle says, is recklessness. Yeah, it's like, I'm going to jump out of this plane.
Starting point is 01:12:21 Yeah, right. I'm going to go around half-cocked. I'm going to get in fights that don't need to happen. I'm going to take risks that don't need to happen. I'm going to risk more than I actually need to risk, right? So also, I think if you're not a driven person, self-discipline is something you need. If you are a driven, ambitious person, you actually need self-discipline about your self-discipline. Tom Brady's struggle isn't like, how do I get out of bed this morning and be great at football?
Starting point is 01:12:50 It's like, how do I sit down and relax? Yeah, how do I keep this under control so I can be a good father? Yes. So I don't overtrain and hurt myself. So I don't go too hard on my teammates. Right. So I can sustain this over a long period of time, right? How can I be patient? So self-discipline, depending on where you are, what phase you are, manifests
Starting point is 01:13:14 itself very differently. Like for me, I'm more on the, I need to ratchet it down. I need to think about, you know, not forcing it. Like, so I'm here, I'm doing press for this book. You asked me before, you're like, what's the next book? Because I am always working on the next book. But I had to go like, okay, these two weeks, I am doing stuff for this book. Right. Now I'm already going to the next one. I don't need to be whipping myself for not doing the other stuff at the same time. That's not fair to the work, to me, to my family. So to be able to be like, I'm gonna turn this down and I'm gonna be present and I just actually do
Starting point is 01:13:58 the thing that's in front of me. Yeah, I feel like every writer feels inferior to Ryan Holiday because you always have, you've got the book out and you're have, you've like got the book out and you're like, well, I have the next three done. And those are coming out in six months and the next six months and everyone's like, how do you do this?
Starting point is 01:14:11 You're a machine. So for me too, it's like, if you told me I could put out a book every three months, like I might, like I'd be like, oh. But actually my struggle is more like, I gotta space them out for, even just for like- Let them breathe. Yeah.
Starting point is 01:14:25 That's harder for me to do than to not work. So we all have, it all manifests itself differently for different people. So what do the Stoics talk about when it comes to self-discipline then? Is there learning a discipline for yourself that works? Is it, what is the philosophy of self-discipline in general? Well, one of my favorite things for the Stokes in self-discipline would be the reminder
Starting point is 01:14:50 that it's called self-discipline, right? Like you can't hold other people to your standards. Mark Sprella says, tolerant with others, strict with yourself. Say again, tolerate? Tolerant with others,
Starting point is 01:15:03 strict with yourself. Oh, interesting. You like, for instance, Kobe Bryant struggles with yourself. Say again, tolerate? Tolerant with others, strict with yourself. Oh, interesting. For instance, Kobe Bryant struggles with this. He was trying to push his teammates to be like him. Rick Fox was like, dude, we're not all Kobe Bryants, right? And that is a lesson. That's not a lesson that most people have to learn, but that's a lesson that some people have to learn. Tolerant with others, strict with yourself. Yeah. You can only hold yourself to your standards. You can't be like, why isn't this person waking up at the time that I am? Well, it's because it's not their company. Right. Exactly. They don't care as much. They don't care as much. And they just haven't found that thing yet. And so you can only hold yourself to your standards. And I've struggled with that where it's like,
Starting point is 01:15:46 if you want to go around being disappointed and angry at people all the time, then sure, try to hold them to your standards. If you want to have friendships, if you want to have relationships, if you want to be happy, if you want to be encouraged, you got to be like, everyone's on their own journey.
Starting point is 01:16:01 They're all doing the best they can. And like, I'm going to meet them where they are. What about finding peace? How do the Stoics find inner peace? We tend to associate Buddhism with inner peace. But my book on stillness, which is called Stillness is the Key, the Stoics talk about this too. A lot, actually. Mark Stoics says you want to be like the rock that the waves crash over and eventually fall still around.
Starting point is 01:16:27 And so I love the idea that like the world is spinning faster than ever. It's noisier than ever. But like I'm going to be calm and chill and locked in. And actually, I think you know this from the sports stuff, is like the athlete is stillest when the game is the most intense. Most chaotic. Yes. Well, in order to perform at your highest level, that's when greatness comes about. Yeah. When there's 10 seconds left, the play is the last play of the game.
Starting point is 01:17:01 You fell down. You've got to get back up. You've got to make the play. Otherwise, you of the game, you fell down, you've got to get back up, you've got to make the play, otherwise you lose the game. It's almost like you learn how to calm yourself under the most pressure. Otherwise, you will not succeed at your goals. And you'll ask, like, LeBron James, what were you thinking? And he's like, nothing.
Starting point is 01:17:22 You know, like, that's when the training takes over. And I think you see this where, like, okay when the training takes over. And I think you see this where like, okay, the world falls apart 18 months ago. And like, actually, most of us did a really good job. We were like, all right, what do I got to do? You know, like, what do I do to keep people I love safe? What decisions do I need to make? What precautions do I need? We were just like locked in because it was, we knew it was serious. But then you're like, get a flat tire
Starting point is 01:17:50 and you're like, what the fuck am I supposed to do? You know, like, so it's like, it's like how like, if your arm got cut off, you'd go into like some state of calm. Yeah, you'd be like, okay, where's the hospital? Yeah. Go give me a belt and like call 911. Right. And like, you know, you, but.
Starting point is 01:18:07 You scrape your knee and you're like, ah. Right, right, right. You break, you jam your finger playing basketball and you're like, I don't know if I can work tomorrow. You know, like the minor stuff, because you have the luxury of freaking out, you do. So I think courage and self-discipline are related there. The ability to be like, my emotions want me to do X, but X is not helpful. What's been the hardest thing for you to overcome in the last few years in terms of emotional triggers that maybe used to or always tend to get under your skin? That you really learn self-discipline or stillness or meditation to become better at? Maybe you haven't
Starting point is 01:18:46 perfected it yet, but like it still bugs you when this happens or that happens, but what's the emotion you've had to learn to master the most? I mean, I think all, I would say the majority of driven people struggle with temper, like your temper, because you want things to be a certain way. You want it to be done yesterday. Yes. A certain way. Yes. And so you get frustrated that they are not, that it's not how you want it to be, how you asked it to be, how you would do it.
Starting point is 01:19:16 So I think the one I'm constantly struggling with is, is, is anger. Really? Not like, not like, I would say like, I don't have an anger problem, but anger is a problem. Right, right. Right, you know, like it's not the same. It's just not good. Right.
Starting point is 01:19:32 And just realizing that it almost never makes things better. I'm never glad that I lost my temper. Most of the things I regret have to do with my temper. It's like, why did I send that? Why did I say that? Now, I think as you work on it, there
Starting point is 01:19:55 are moments where you need to make a display of anger to accomplish something. But that's not the same as feeling it regularly. or as being out of control from your anger. Right. Like, um, coaches in the NBA will sometimes take a technical, like they'll get angry on purpose to like send a message to the ref or rile the team up. That's different than getting in a fight. Right. Um, and needing to be restrained right so um for me it's just like is anger going
Starting point is 01:20:27 to make this better what am i really upset about i would say anger is the big one and then the other one would be like just anxiety i think like the pandemic when all of a sudden i was doing a lot less stuff like what are you not i realized like oh i thought I was anxious about like needing to get to the gate before my flight, but I was really just anxious, period. So it's like, you know, like now that I'm not traveling and I'm still feeling the anxiety, nowhere to go, nothing to do, and the anxiety is still there. It's like, oh, anxiety is one for me. What do the Stoics say on how to let go of or heal anger and anxiety? What's the process of healing the anger challenge, temper challenge that I think a lot of people have faced or the anxiety anxious challenge? The anxiety one is my favorite. Mark Spiro says,
Starting point is 01:21:23 like, today I escaped anxiety. And he goes, no, because he's writing to himself. Like, you're looking at the journal of the most powerful man who ever lived. It's beautiful. Because I escaped anxiety. And he goes, no, I discarded my anxiety because it was within me. The anxiety was within you. Yes. Like, the anxiety is a creation.
Starting point is 01:21:43 Like, almost all the things that I am anxious about, nobody else cares about. They're not anxious about it in the same way. Or it's just like I imposed this deadline and it's arbitrary. And now I'm stressed about it, right? I just talked to someone on my team about this. I was like, okay, obviously I want this to get out by this certain date. And I'm worried that if we don't, the customers will be upset or worried or whatever. And I was like, so we're still going to work very hard to hit this deadline.
Starting point is 01:22:15 But here's the email we're sending out now explaining to people all the factors that are going into it, why it may take longer than expected, what the conditions the pandemic has created, so on and so forth, and just to be patient. And so now I still want to hit the deadline, but I don't have this sort of self-imposed anxiety or worry that there's all this stuff that people don't know about. And that, you know, like I'm just going to go like, hey, I'm going to manage my expectations. I'm also going to over- that you know like I'm just gonna go like hey I'm gonna manage my expectations I'm also gonna over communicate and then I'm gonna detach a little bit right okay so that's what the anxiety what about with anger what they say about letting that go anger would be
Starting point is 01:22:58 Seneca says getting angry is like returning a bite to a dog or a kick to a mule. You know, like so often what you're angry about, you're just really expressing this like, I wish that hadn't happened. Yeah. And it's like, okay. But it happened. It did. So like what is this accomplishing?
Starting point is 01:23:20 And so I think for me, I think a lot about like, who's being punished here? Mostly me, like I'm feeling. The anxious and angry person is being punished. Yes, I'm punishing myself by deciding to carry this around. And that I think the other thing that can be helpful is like, have you ever looked at yourself when you're angry? You don't look good. Like, yes.
Starting point is 01:23:43 You don't look good. You don't look good. You don't look good. And I think one of the scary slash things about being like a public figure or something is you're like, you can catch, you go like, what do you think people would think if they saw this? Right?
Starting point is 01:23:57 And that is a stoic exercise. Like, what would you look like? What would an indifferent person, like a person who didn't know you, just standing here in this, like, would you be doing this if people could see? Probably not.
Starting point is 01:24:12 And so just sort of going like, this is not a good look, man. This is not what you want to do. At the end of the day, do you look yourself in the mirror ever and ask yourself like, how did I do today? Did I show up to the standard that I want to of the Stoics or of my own standard today? Or how do
Starting point is 01:24:30 you process and assess your day, whether it was up to your standard or below your standard? Do you journal? Not consistently, but I do it. Yeah. I kind of like mental journal, you know, or verbal journal. Same thing. Yeah, yeah. Verbal journal. So for me, it's journaling. And I think it's almost impossible to separate stoicism and journaling. That's what it is.
Starting point is 01:24:51 Meditations is Mark Ceruleus' journal, right? Seneca's work survives to us in letters that he wrote to a friend, also kind of a form of journaling. So for me, like, I do that reflection. Obviously, in my work, I'm always thinking about these things, so I have kind of an advantage. That's one of the benefits of like you're always working through your stuff with guests or interviews. I'm always revealing my shame. Yeah. It's work that if you were a different kind of entrepreneur, you would have to have a different medium to do it in.
Starting point is 01:25:22 Right. But for me, the journal is like the private different medium to do it in. But for me, the journal is like the private space that I do that in. So like, what am I working on? Where am I falling short? What do I need to be thinking about? What am I proud of? What am I grateful for? I'm just trying to talk through that stuff on that page. And I would say the last year especially has been really good because it was overwhelming. It was not normal, right? Like it was more spent a year and a half in quarantine with two kids under, right? Like that's not healthy, right? Like that's not what anyone would choose. And so you do that. Like if you don't have an outlet, where does that go?
Starting point is 01:26:08 Comes out in anxiety, anger, fear, all those other places. So I think if you can work either in the morning or at night on a page, Anne Frank says, "'Paper is more patient than people." Just work it out there instead of vomiting it on people. On people, yes, on people. Just work it out there instead of vomiting on people. What are the exercises or the hobbies that you dive into in order to release anxiety and anger besides journaling? So every morning, it fluctuates a little bit, but I do some form of walking and
Starting point is 01:26:42 some form of physical exercise, an endurance thing and then usually i do some like training like three to four days a week also so it's like mostly physical walking running swimming so walking walking is not the exercise walking is like for the meditation and then i run swim or bike every day really And then I'll do like some kind of weight or body weight stuff a couple days or two. Really? Yeah.
Starting point is 01:27:09 You do like 10, 15 miles a day, I feel like. Don't I always see your Not that much. Your watch posts every day. I do run a lot. And then I've tried to merge like running and kid time.
Starting point is 01:27:19 So like I put them in the stroller. That's smart. This morning I ran with the kids. But I like to, to me because like my job is sit in the chair, like this morning i ran with the kids but um i like to to me because like my job is sit in the chair stare at a screen i want the hobbies to be the opposite of that outdoors or activities or physical yeah that's cool uh where would you like to be a year from now you had 18 months of this where you probably were faced with your anxieties or temper or whatever more frequently.
Starting point is 01:27:48 A year from now, where would you like yourself to be with your inner world? Well, you know, people, you probably heard yourself saying, I've heard a million people say, I can't wait for things to go back to normal. Right. And I want the opposite of that. Like, first off, normal doesn't exist. Yeah. Second, if normal does exist, normal caused this. So I want to preserve what has been maybe the largest lifestyle experiment in human history. Right?
Starting point is 01:28:18 Like, what does less look like? What does more family time look like? What does, you know, like, more focus look like? You know, what does that look like what is you know like right uh more focus look like you know all what does that look like for me it's like how do i preserve those things in an environment where i now can do other like it was easy to not travel for speaking for 18 months because like there were no live events right but now and i'm sure you're seeing this, like now the offers are coming in. And to be like, that's very generous, thank you, but I'd rather not.
Starting point is 01:28:51 Right. That's not just hard to do, it's scary to do. Because like there's a part of you that's like, what if five years I'm kicking myself because I need that now. Right. Or like, what if they never, what if they're offended? You know, what if I miss on this opportunity? You know, like FOMO is real. So how are you making your decisions
Starting point is 01:29:11 based on like travel and speaking and opportunities? Are you making them based on like, if you really want to do it or if it's a certain pay that's like absurd, you're like, okay, I have to do this because it makes sense now. I'm having to think about it. I mean, I was doing the math because I did my first in-person like a couple weeks ago.
Starting point is 01:29:31 And it was really safe. It was actually done by an air filtration company. So it was like couldn't have been us, who, by the way, is killing it as a business, as you can imagine. But I realized that on, on that night, I was ending a streak of like 530 consecutive bedtimes with my kids. Wow. That I'll probably never get ever again.
Starting point is 01:29:54 That you put them to bed. Yes. With my wife. I'm not saying I did this by myself, but like I was, I slept in the same house as my kids, did the same routine for 535 nights pretty impressive and i'll i mean i've probably never gone that many nights without traveling
Starting point is 01:30:12 in my whole life even when i was a kid right like that's impressive so i'll never get that again and so now really like opportunity costs are a hard thing to keep track of because they're hidden. And sometimes when you step away from something or you try it in a new way, you realize, oh, yes, this is lucrative. Yes, this is fun. Yes, this gets me attention or builds a business. But it comes at the expense of quiet evenings at home. Being more connected to the work. Being like, let's say,
Starting point is 01:30:49 if you travel in a week, your interviews that week are 5% less good. Right. It's really hard to notice that. But over a long enough time, that's actually a huge decrease in quality. Absolutely. And so I think for me, if I'm like, where am I a year from now?
Starting point is 01:31:08 I'd like to think my goal would be to be in a very similar head and spiritual place, even though life will have resumed some of the busyness and obligations that do you know, do have to resume. Sure, sure. What's the thing you're most proud of in the last 18 months? I mean, that bedtime streak is a big one for, I mean, that's like, it means a lot to me, but I would just say that like, you know, the world melted down and I was able to do good work
Starting point is 01:31:48 that I think mattered inside of it. I started this book, I'd sold it before the pandemic, but I started it on June 16, 2020. So in the middle of the most difficult world event of my life, I did good work. I'm proud of that. We got to get the book. Courage is calling. Fortune favors the brave. Isn't it usually fortune favors the bold?
Starting point is 01:32:16 Yes, it is. Why'd you change the brave? Because courage and bravery has sort of worked. But you know, that expression, which is a lovely Latin expression, you know, it's actually about this guy named Pliny the Elder, who's a naval admiral, and Mount Vesuvius explodes. And he went to rescue his friend.
Starting point is 01:32:36 So when he's saying, basically, he's trying to get into this harbor where his friend is trapped. And the pilot says, the the captain says we can't get in there it's too dangerous there's too many rocks and he says uh fortune favors the bold like head towards my friend so we think that that expression means like be a visionary like take risks you know do like the do the the bold thing. Which it does mean that. But he meant it in a selfless context.
Starting point is 01:33:11 And in fact, he dies in the course of the rescue. Which I feel like is a really important spin on a story that people would kind of miss the point on. It doesn't mean, like, plunge ahead. Don't think of the consequences. It means, like like dive into the water to save someone who's drowning. That's inspiring. Yes, fortune favors the brave. Courage, you know, something, courage is like,
Starting point is 01:33:36 for me, I feel like you should really lean into things that are hard for you to have courage on. You know, for me, it's easy for me to think of like, okay, if someone gets in a car crash, my reaction is stop the car, go out and go and pull someone out. Maybe it's because of my size. Maybe it's because of sports background. That's kind of like my reaction.
Starting point is 01:33:56 It's hard for me to tell my girlfriend something I don't want to tell her. It's hard to be like, man, this takes a lot of courage for me to be like, oh, I'm really going to be honest here. How is this going to tell her. Yes. It's hard to be like, whew, man, this takes a lot of courage for me to be like, ooh, I'm really going to be honest here. How is this going to impact her? Yeah. Is it going to change every,
Starting point is 01:34:11 you know, whatever it is. Sure. And I think it's important for us, I don't know if you have a practice or if you have this in the book
Starting point is 01:34:17 where like exercises on how we could start implementing courage on a daily process, whether it's say the thing that's hard for you to say to your boss or to your friend or to your process, whether it's say the thing that's hard for you to say to your boss
Starting point is 01:34:26 or to your friend or to your parent, whatever it is, or do the physical activity that's hard for you. Do you have any of that we can think about as well? Yeah. I mean, obviously the book is sort of breaking it down and going in the ways that we do that. But I, I, you know, there's that cliche, the simple ways, like that cliche about like do one thing every day that scares you yes it's kind of hard to beat that you know that's like sometimes these things are cliches for a reason like because i think if you build it as a habit you're gonna be more likely to do it when it counts um and so like when you've done scary i think this is your point about the pandemic. If you've been through stuff before, it's easy to know what to do. If you've avoided difficult things, if you don't have a practice of plunging ahead,
Starting point is 01:35:16 and even just turning the knob to cold in the shower. Who's in charge? I do the scary, hard thing because I'm in charge. You're going to be able to do that when you know when it counts hopefully what are the uh what are the the either the navy the army or the marine i can't remember who but what's the saying it's like we rise to our training we fall to our training we don't rise to our expectations or something or? Yeah, yeah. You think that it's going to be like, oh, my best, this situation will bring out my best self.
Starting point is 01:35:49 Maybe, but probably not. Right. It's what's your worst best? Your worst best. On your worst day, like how good can you be? Train for that consistently because you're going to fall down to that.
Starting point is 01:36:02 If you're better than that, great. Well, as a runner, you train your T-pace, right? You're like, what's 90% of your best, your all-out max capacity? Train at that. And then it becomes easy. And then so when it happens, and this is what we're talking about,
Starting point is 01:36:20 preparation makes you brave. You've done the work. Put yourself in a position where you're like, this is what this was all for yes get a few copies for friends i'm telling you courage is calling here's the thing every one of ryan's book becomes a bestseller at some point so whether it's gonna be best selling the first week or first year or first 10 years it's going to be it's going to be number one at some point i I'm telling you, let's support him in getting to number one sooner than later, even though it's not his intention right now, but it'll definitely help get the mess out to more people. And I think courage is one of the values that
Starting point is 01:36:57 humanity lacks the most. Having the courage to stand up for what's right. Even sometimes you might be wrong later in life, but like having the courage in that moment, like at least I stood up for what I thought was right. Having the courage to say the truth, having the courage to be in integrity with yourself, having the courage to just continue to show up as a good human being. It's not easy in a selfish world.
Starting point is 01:37:21 It's not easy to have courage and stand for what's morally right and what's the win-win-win for the situation. Now, how can I win at all costs? And where would we be without those people? If you think things are bad now, where would we be without those people in the past? And so you can be one of those people today. Absolutely.
Starting point is 01:37:43 Be a symbol of inspiration. So get the book anywhere books are sold. Amazon. What's also the best place for your site so they can learn more about this and all your books? Yeah. Dailystoic.com. I do a free email about stoicism every day. It's a great email list. And then my social media. At Ryan Holiday. At Daily Stoic. And if you want to see a YouTube sensation, go to your YouTube, youtube.com slash Ryan Holiday, right? No, Daily Stoic.
Starting point is 01:38:09 Daily Stoic, yeah. Some really great videos there actually from Stoicism and you guys do like great storytelling and visuals on that stuff. But now you're vlogging
Starting point is 01:38:16 so you're a superstar on the YouTubes and the TikToks. Yikes. This is a question I ask everyone at the end. It's called the three truths.
Starting point is 01:38:26 I think you've answered it before, but let's see if something comes up different for you. Imagine it's your last day on earth many years away and you've accomplished everything you want to accomplish. You're as old as you want to be, but eventually you've got to turn the lights off. And you've lived the life. But all of your written audio or video work has to go somewhere else. Okay. It doesn't stay in this world.
Starting point is 01:38:48 Okay. So no one has access to this interview or anything you've ever put out in your life. But you have a piece of paper and a pen. You get to write down three truths. Three lessons that you've either learned, that you've experienced, or that you want to share with the world. And this is all the lessons we would have to remember you by. Okay. From all your work or what you know about life, what would you say are those three truths for you? Let's start at the bottom. Life is very short, right? So memento mori, you've got a brief moment here right life is short to all accomplishments are
Starting point is 01:39:28 ephemeral what matters is what you do for the people you care about okay actually Jackie Robinson's tombstone is a life is not important except for its impact on other lives. So some version of that. Yes. Interesting. And then the first would be, what would I say? Do what you love. There you go. Do what you love. There you go. Do what you love.
Starting point is 01:40:10 Before I ask the final question, I want to acknowledge you, Ryan, for being an incredible human being. You constantly show up every year. I've known you for 10 years. Yeah. You constantly improve your life. You do what's right for you.
Starting point is 01:40:24 You invest in your family. You invest in your health. You do what's right for you. You invest in your family. You invest in your health. You invest in creating art for the world to be a better place. You do, and you're constantly acknowledging where you could improve. Anxiety, anger, temper. And for me, you're taking ancient wisdom and teaching it in a new, fresh, practical way while using your creative mastery, your writing, and your skill set. So I want to acknowledge you for always showing up, for being a leader in so many different ways in the world, writing being the most way that people see and read your writing, but in other ways behind the scenes that people don't know about that I do know about. So I acknowledge you for how you keep showing up, man.
Starting point is 01:41:08 You're a brilliant human being, extremely talented, probably one of the most talented writers I've ever met and of our time. So I really acknowledge you for all the gifts you have. That's very nice. Of course, man, of course. So if your wife doesn't tell you that every day, she needs to start telling you that, right? Final question, what's your definition of greatness? So if your wife doesn't tell you that every day, she needs to start telling you that, right? Final question, what's your definition of greatness? Definition of greatness. Fulfilling one's potential.
Starting point is 01:41:34 So I think it's very easy to define greatness by some sort of external standard, right? Like, do they have the most? Did they win the most? Did they get this or that, right? And I like to think that as you get better at what you do, you care less and less about that and more about, did you do everything you were capable of doing?
Starting point is 01:41:55 Did you take whatever hand you were dealt or set of assets you were given and did you play them for all they were worth? assets you were given, and did you play them for all they were worth? Right. Like, did you leave anything on the table? If the answer is yes, then that's not greatness. If you touched however briefly, the full, you tapped in however briefly to the full measure of your powers, that's greatness.
Starting point is 01:42:21 Maybe you get it for a whole career. Maybe you get it for one thing one moment you know but that that maybe nobody sees it but that's but greatness is that there you go right how they my man appreciate it the best thank you so much for listening i hope you enjoyed today's episode and it inspired you on your journey towards greatness make sure to check out the show notes in the description for a full rundown of today's show with all the important links. And also make sure to share this with a friend.
Starting point is 01:42:50 Leave us a review over on Apple Podcasts and subscribe over on Apple Podcasts as well. I really love hearing feedback from you guys. So share a review over on Apple and let me know what part of this episode resonated with you the most. And if no one's told you lately, I want to remind you that you are loved, you are worthy, and you matter.
Starting point is 01:43:09 And now it's time to go out there and do something great.

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