The Rich Roll Podcast - Ryan Holiday On the Pursuit of Virtue

Episode Date: October 25, 2021

This cultural moment bears witness to a growing distrust of institutions unprecedented in our lifetime. With it comes an unraveling of healthy communication. Tearing others down has taken priority ove...r rising ourselves up. And binary thinking, divisiveness, and fear-based behavior have supplanted sense-making, appreciation for nuance, and mutual respect. For Ryan Holiday, the antidote is the pursuit of virtue—specifically, the virtue upon which all other virtues sit, courage: the ability to rise above fear and to do what’s right. Returning for his 4th appearance on the podcast, Ryan is one of the world’s bestselling living philosophers globally lauded for adapting Stoicism to the mainstream. His books—including The Obstacle Is The Way, Ego Is the Enemy, The Daily Stoic, and Stillness Is the Key—have sold over 4 million copies and spent over 300 weeks on the bestseller lists. Ryan’s expertise in mining the modern-day practicalities of ancient philosophy to live more optimally is coveted by some of the world’s most successful CEOs, political leaders, world-class athletes, and NFL coaches, and he’s here today to help us make sense of this current moment through the lens of his latest book, Courage Is Calling. This is a conversation about the challenge of sense-making amidst our national divide. It’s about the application of time-tested wisdom, the nature of virtue and why doing the right thing is always the right thing. We cover it all: the perils of individualism, responsibility as a counter-balance to liberty, fear, courage, partisanship, tribalism, and why virtue is both a craft and an action verb. To read more click here. You can also watch listen to our exchange on YouTube. And as always, the podcast streams wild and free on Apple Podcasts and Spotify. I relish my conversations with Ryan—he is a compelling thinker about things that matter, and this one is chock a block with practical wisdom, things we can learn from philosophy and history to make sense of today, and most importantly, to live and be better humans and citizens. Peace + Plants, Rich

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Starting point is 00:00:00 When we think about courage, it's like we all know what it is. We all admire it. We all know what it can do, and yet it's relatively rare. Like, it's one of those weird things where it's like we're all in agreement that courage is important, and then we're all sort of looking around being like, why aren't people more courageous? We seem to ask ourselves that question less, right? We all have strong opinions about the lack of courage of our elected officials or public figures or whatever, but we're very rarely holding ourselves to the standard
Starting point is 00:00:34 that we're asking them. The Rich Roll Podcast. I think it's fair to say that we live in a pretty confusing time, a time of growing institutional distrust, a time of erosion with respect to healthy communication, a culture in which taking others down has become more important than rising ourselves up, and a moment in which sense-making, appreciation for nuance, and mutual respect have been supplanted by binary thinking, divisiveness, and perhaps most of all, and most pernicious, fear-based behavior.
Starting point is 00:01:28 For today's guest, Ryan Holiday, returning for his fourth appearance on the podcast, the antidote can be found through the pursuit of virtue. And the virtue upon which all other virtues sit is courage. The ability to rise above fear, to do what's right, to do what's needed, to do what is true. Best known for pioneering stoicism to mainstream adoption, Ryan is considered one of the world's best-selling living philosophers. His books, which include The Obstacle is the Way, Ego is the Enemy, The Daily Stoic, Stillness is the Key, and several others, have sold over 4 million copies and spent
Starting point is 00:02:15 over 300 weeks on the bestseller list. Ryan's expertise, that being the mining of modern-day practicalities of ancient philosophy to live more optimally is coveted by some of the world's most successful CEOs, political leaders, world-class athletes, and NFL coaches. And he's here today to help us make sense of this current moment and how ourselves, we can live and be better through the lens of his latest book,
Starting point is 00:02:45 which is called Courage is Calling. More to add in a sec, but first. We're brought to you today by recovery.com. I've been in recovery for a long time. It's not hyperbolic to say that I owe everything good in my life to sobriety. And it all began with treatment and experience that I had that quite literally saved my life. And in the many years since, I've in turn helped many suffering addicts and their loved ones find treatment.
Starting point is 00:03:19 And with that, I know all too well just how confusing and how overwhelming and how challenging it can be to find the right place and the right level of care, especially because, unfortunately, not all treatment resources adhere to ethical practices. It's a real problem. at recovery.com who created an online support portal designed to guide, to support, and empower you to find the ideal level of care tailored to your personal needs. They've partnered with the best global behavioral health providers to cover the full spectrum of behavioral health disorders, including substance use disorders, depression, anxiety, eating disorders, gambling addictions, and more. Navigating their site is simple. Search by insurance coverage, location, treatment type, you name it. Plus, you can read reviews from former patients to help you decide.
Starting point is 00:04:17 Whether you're a busy exec, a parent of a struggling teen, or battling addiction yourself, I feel you. I empathize with you. I really do. And they have treatment options for you. Life in recovery is wonderful, and recovery.com is your partner in starting that journey. When you or a loved one need help, go to recovery.com and take the first step towards recovery.
Starting point is 00:04:44 To find the best treatment option for you or a loved one, again, go to recovery.com and take the first step towards recovery. To find the best treatment option for you or a loved one, again, go to recovery.com. We're brought to you today by recovery.com. I've been in recovery for a long time. It's not hyperbolic to say that I owe everything good in my life to sobriety. And it all began with treatment and experience that I had that quite literally saved my life. And in the many years since, I've in turn helped many suffering addicts and their loved ones find treatment.
Starting point is 00:05:14 And with that, I know all too well just how confusing and how overwhelming and how challenging it can be to find the right place and the right level of care, especially because unfortunately, not all treatment resources adhere to ethical practices. It's a real problem. A problem I'm now happy and proud to share has been solved by the people at recovery.com who created an online support portal designed to guide, to support, and empower you to find the ideal level of care tailored to your personal
Starting point is 00:05:46 needs. They've partnered with the best global behavioral health providers to cover the full spectrum of behavioral health disorders, including substance use disorders, depression, anxiety, eating disorders, gambling addictions, and more. Navigating their site is simple. Search by insurance coverage, location, treatment type, you name it. Plus, you can read reviews from former patients to help you decide. Whether you're a busy exec, a parent of a struggling teen, or battling addiction yourself, I feel you. I empathize with you. I really do. And they have treatment options for you. empathize with you. I really do. And they have treatment options for you. Life and recovery is wonderful. And recovery.com is your partner in starting that journey. When you or a loved one need help, go to recovery.com and take the first step towards recovery. To find the best treatment
Starting point is 00:06:40 option for you or a loved one, again, go to recovery.com. treatment option for you or a loved one, again, go to recovery.com. Okay, Ryan Holiday. I always relish my conversations with Ryan. He's just such a compelling thinker about things that matter. And this conversation, much like our other conversations, is just chock-a-block with practical wisdom. It's all about what we can learn from philosophy, what we can learn from history in order to make better sense of today. And most importantly, live and just be better human beings. So I think that's all I wanna say
Starting point is 00:07:20 about the conversation to come. So without further ado, here we go. Please enjoy my conversation with Ryan Holiday. Ryan Holiday in the house, good to see you, man. Yeah, it's been two years. Has it? It's been two years. It's this weird thing where time seems to move really slow
Starting point is 00:07:40 and really fast simultaneously. So I can't remember things that happened yesterday and things that happened two years ago feel like yesterday. Yeah, there's a James Salter novel that the title, it's like his memoir, I guess it's a memoir, but the title is burning the days. And that's like a phrase I've thought a lot about during the pandemic that it just feels like
Starting point is 00:07:59 they're all just like burning together kind of, you know, like it's like it could be last week or it could have been two years ago and it all feels roughly the same distance from each other. I feel like this deep sense of irony in that the last time that we spoke, it was about your book, Stillness is the Key. And in the wake of that conversation,
Starting point is 00:08:21 we were met with the pandemic and that compelled us into this forced repose where we have the opportunity to engage with stillness, to really reckon with what's most important, to discard that which no longer serves us and all of that. And you would imagine with that, that we would emerge better human beings. And yet I feel like we're more divided, more separated,
Starting point is 00:08:48 more acrimonious. I feel like we're teetering on kind of like social collapse at the moment, as opposed to what we could have kind of learned throughout this period. Well, people are often very flippant about like meditation, for instance, like everyone should meditate, spend. And you realize like that spending time alone
Starting point is 00:09:09 with your thoughts may be like the absolute worst prescription for a certain type or a group of people. And so while some of us used the last 18 months to reflect and grow and like reevaluate lives and priorities, you can tell that a lot of people came, I sort of liken it to, it's like you catch a flash of truth or yourself or insight
Starting point is 00:09:38 and you can look at it and face it or you can turn away and run the opposite direction. And I think some people as the world slowed down and they were forced to look at like everything, decided I don't wanna look at that because if I look at it, then I have to make changes. And so maybe that's why they went down this rabbit hole or they got consumed with this. I also think that's why they went down this rabbit hole or they got consumed with this.
Starting point is 00:10:06 I also think it's why a lot of people moved or quit their jobs or got divorced. It's just like anything to not have to sit quietly with your own thoughts. Which is terrifying. Yeah, I mean, there's that Blaise Pascal quote. He says like to sit quietly in a room alone is like the hardest thing that a human being could possibly. Or how is quote, he says like, to sit quietly in a room alone is like the hardest thing
Starting point is 00:10:25 that a human being could possibly get. Right, or how is it you said something like, maybe it's the same quote that the summation of suffering can be drilled down to man's inability to sit alone with himself. Yeah, I think that is the quote. It's like, instead of, like doing nothing is actually like the hardest thing in the world.
Starting point is 00:10:47 And so people found, I mean, some of us positive, they learned how to bake bread, but also- Yeah, but that had its own shelf life. We quickly tired of that. I think, you also have to layer on top of that, a very real fear of getting sick and then all of the stressors and anxiety
Starting point is 00:11:09 that gets packed into the uncertainty of the moment, which of course, without tools, is going to manifest in bad behavior all across the board. Well, I think at the root of all unstillness is that sort of vague floating fear of death. Like, what does it all mean? How long do I have? Where do I go after I die? And so there's nothing quite like a deadly virus floating through the air, you know, randomly picking off people, people that you know, people that you've heard of, in enormous statistical numbers
Starting point is 00:11:47 that are posted online every day to sort of stir up all of those feelings of restlessness and fear and anxiety. Yeah, and of course, fear expressed is anger, resentment, all the kind of discord that we're seeing being sown across every kind of sector of humanity. Well, yeah, it takes an immense amount of self-awareness to go like, I'm feeling discomforted because of X,
Starting point is 00:12:15 or I'm feeling anxious because of X. You know, I think that was something for me that I found during the pandemic where suddenly I wasn't doing anything. So I wasn't having to get to this plane. I wasn't stuck in traffic here. I wasn't having to prepare for this or that. And so you'd think that my anxiety would go way down,
Starting point is 00:12:35 that suddenly you'd have a lot less to worry about. And then actually that's not true. And then you realize, oh, the anxiety has nothing to do with any of the things. It's actually Mark Stratus talks about this in meditations. He says like, oh, the anxiety, he says, I escaped anxiety. And then he goes, no, actually I discarded it. And he writes this during a plague, no less,
Starting point is 00:12:56 but he goes, I discarded it because it was within me. And then, so that was a breakthrough I sort of had. It was like, oh, I thought I was stressed and anxious and worried because of all of these very reasonable things that cause those things in your life, work, family stuff. And then when all that gets pared down, you realize it's like, oh no, it was me. Yeah. I'm the common variable. The anxiety is free floating, right? And when you occupy yourself through travel and work and all the things that we do,
Starting point is 00:13:29 those are ultimately distractions from the anxiety and not necessarily the thing that's provoking the anxiety. The anxiety exists independent of that. And left to our own devices and compelled to sit still, reckoning with that becomes a challenge for anyone. Yeah, and when suddenly you can't express yourself through accomplishments or busyness or activity. And your identity being wrapped up in that,
Starting point is 00:13:58 I plead guilty to that. Of course, no, again, to have to slow down, I think for me, it was like to have to slow down and just do the work. It was like, just do like, it's like, oh, I am, weirdly, the good part about the pandemic was as much closer to what I should be doing day in and day out, which is like,
Starting point is 00:14:17 wake up, spend time with my family, take care of my health and write. Write books. Yeah, not almost all the other stuff was impossible or if not illegal for short periods of time, right? And it's like, okay, so I can do that. and write. Write books. Yeah, not almost all the other stuff was impossible or if not illegal for short periods of time, right? And it's like, okay, so I can do that. And it's funny though, because now, you know, it's like,
Starting point is 00:14:34 let's, I want things to go back to normal. That's what we say. And like normal is what caused this. Yeah, but now I think we're all understanding that we're never gonna return back to that idea of normal. We're gonna have to frame a new normal. And what we're contending with is something that is probably going to persist
Starting point is 00:14:58 and be some component of our life or lifestyle for who knows how long. Yeah, and I mean, I think the thing that people struggle with the most when it comes to stoicism is this, it's often associated with like sort of resignation. Like the stoics use the word ascent, not like ascent up a mountain, but A-S-S-E-N-T,
Starting point is 00:15:21 like I ascent to this, which I actually think is a really important and poorly understood concept. Surely in the ancient world, we had a lot less agency over things. Like you were born in a certain class, you lived in a certain place, your life expectancy was much lower,
Starting point is 00:15:39 tragedy, tyranny, all these things, these larger forces than you exerted a lot more influence over your life. So as we've rightfully broken out of that, you can get to a place, and I know you know this from recovery work, which is like, you start to think like, not only is there no higher power, you are the higher power,
Starting point is 00:15:58 like you're in control. And so you get, you have trouble with the idea of ascent. And I think even as we were looking at this with COVID, there was this brief moment, not that long ago, where it was like, we have beaten this, it is going away. And now we're reckoning with the idea of like, no, it's endemic, it's here forever. And I've been thinking about that.
Starting point is 00:16:20 It's just like, first off, the unpleasantness of it, second, the unfairness of it, Second, the unfairness of it. It's not my fault. I feel like I made all the right choices. I did what I was supposed to do. And yet here we are, that idea of just like, and so it goes, like, this is it. You just have to ascend to it.
Starting point is 00:16:39 Yeah, it's a graduate course in what in recovery parlance is called surrender, right? Which, you know, on the subject of assent being misunderstood, the idea of surrender being likened to giving up, which is not the case. It's really just an honest reckoning with what you have control over and what you don't, right? These are the facts on the ground.
Starting point is 00:17:02 The idea that when you look at it objectively and truthfully, there is almost nothing that you can control. All you can control is how you comport yourself, how you respond to the world around you, how you react to the environment, the thoughts that you entertain, the people that you choose to surround yourself with and everything else elude your ability to manage.
Starting point is 00:17:24 And I think really embracing that creates a certain kind of freedom that makes you stronger and more capable. And that idea, which was very difficult for me to understand and learn as somebody who was relying on self-will for everything throughout my whole life. And in addiction, they call it self-will runs riot, running riot. It took me a long time to really, not only intellectualize what that meant and then to start living it.
Starting point is 00:17:52 But when you're able to do that, you become so much more competent in every facet of your life. And it segues completely with the idea of stoicism. Yeah, well, it's also just a resource allocation issue. So like if I wake up tomorrow and I'm like, it's unfair that it's this way, it sucks that it's this way,
Starting point is 00:18:14 I wish that it was this other way. Or it should be a certain way. All of that is just not being directed at, I actually gave a virtual talk this morning. I was sort of stumbling over and I accidentally, I was like, so, and then I was like, so what? And I was like, so what are you going to do about it? And you know, like, it's just that,
Starting point is 00:18:35 that's sort of how a stoic would think about it. It's like, you can list this long list of problems and they're like, so, and then, and then, and then, so what? And then, so what are you gonna do about it? That, that's the, that's where this idea of ascent intersects with will. Cause it's not like you want no will, no self-will.
Starting point is 00:18:55 You have to have some of it. You wouldn't be where you were if you weren't able to make the most of, you know, the things you do have control over, but that the sort of intersection between what's up to you and what's not up to you, and then what you do with what's up to you, that's the whole thing.
Starting point is 00:19:13 Well, one of the things that you've done over the course of the past year that I'm really interested in hearing from you on is this bold pivot, which I think you could characterize as sort of, you know, a courageous step. We're gonna get into courage in a little bit. Is opening up this bookstore in a small town in the middle of a pandemic.
Starting point is 00:19:36 I mean, we did our version of that by moving into this studio. Like when everyone's zigging, you zag, you try to find, you know, the opportunity in the setback, so to speak. And you've told the story of the bookstore on YouTube, which I've really enjoyed following, but tell me a little bit about the thinking behind
Starting point is 00:19:56 why you decided to do that and how that's been. Well, so actually when I saw you last, this is when I was thinking about doing it. So when I was on my book tour for Stillness, one of the things I was, I'd seen the space that I was interested in. And then I was like, well, I'm going to go around all these bookstores, like I'll do some research. And my wife and I had been thinking about sort of setting up shop, like literally in the sense that either I worked out of my house or at an office, you know, in Austin, we live a little bit outside Austin.
Starting point is 00:20:27 And we needed something sort of more central, but then also that was like a hub for all the stuff that I do. And we sort of made this crazy leap in, I guess we closed on it like in December of 2019. And then started getting serious about it in January and February of 2020. So like the absolute worst timing you could imagine. I think we hired the first person for the bookstore like two weeks before like everything shut down for the pandemic.
Starting point is 00:21:00 But that sort of goes to the, also the idea of ascent, right? You chose to do something, you wrote the check or you signed the contract and then life's like, oh, you thought it was gonna be this hard. Well, now it's 20 times harder. What are you gonna do? Like you started the race and then you lose one of your shoes or something.
Starting point is 00:21:18 And you have to decide, like, are you gonna quit? Or are you gonna be like, I'm just doing it this way now. But I think for me, the idea of a bookstore is like, I love books and I think they're important. I love physical books most of all. How could I, with the success that I've had, make like sort of a positive contribution to a place that I am both love and am a resident of. So we opened this tiny bookstore on a main street about 30 minutes from Austin in a building that's been there since the 1880s.
Starting point is 00:21:52 Yeah, it's like this historic main street. Yeah, it's basically like Mayberry, like it's this tiny little town. My son, when we were going to school was like right up the street. It's just this old school sort of Americana thing. And I think, I do hope there is something, like I am seeing it more commonly
Starting point is 00:22:16 where like people whose lives, like yours and mine, that's like so internet focused, so like scale focused. You know, like you do a podcast, you reach millions of people. You do a YouTube video, you reach millions of people. Your books, even most of the sales are digital, right? Yeah. And they're all over the world and you don't interact or see any of that. And I think part of it was just like, what if we did something like
Starting point is 00:22:39 real? It could be at a much smaller scale, but it was real and physical and it actually like involved people. And then of course a pandemic comes around and says, actually, no, you can't have any people. So that's been sort of a struggle and adjustment, but it's been cool. Well, the thing about it is that it can be this HQ for all the stuff that you do, as you mentioned.
Starting point is 00:23:01 So you need a place to work to write. So you have that there. You're now doing a podcast, which I wanna talk to you do, as you mentioned. So you need a place to work, to write. So you have that there. You're now doing a podcast, which I wanna talk to you about that a little bit. You can do your podcast there. And you have this retail store. I think you, didn't you sublease like the other half of it so that you could like kind of alleviate the overhead?
Starting point is 00:23:18 Well, the other half was gonna be like events. That's what I was gonna do. And like, so that's not happening. And we rented it to this really cool vinyl record store. So it's just cool to be like looking down from my office and it's like books, music, people in this little town. And I think the nice part about having the stuff at scale is it subsidizes the cool physical stuff.
Starting point is 00:23:44 And to be able to, is it subsidizes the cool physical stuff. And to be able to, it's also just been humbling to do something that's like smaller and less lucrative. You know what I mean? Like, I know that sounds weird, but like to be like, oh, hey, it made $500 today. That's awesome. Right, it's crazy.
Starting point is 00:23:59 Cause like for no capital, you can put content up on the internet and reap financial reward. And this requires a tremendous amount of capital with no remuneration. Yes. It's symbolic, I think. Definitely.
Starting point is 00:24:14 And it's consistent with who you are. But it's cool. Like people will come in and they'll be like, oh, what should I read? And I'm like, you should read Rich Roll's book. Like to physically be able to be like this book. And like, they wouldn't have been able to discover it otherwise.
Starting point is 00:24:28 And then they like, they take it home. Like there's something- Like Quentin Tarantino in the video store in Manhattan beach recommending movies. Yeah, and again, like the math is more like, does it not lose a lot of money? Like success is just different. It's not like how many millions of people watched this
Starting point is 00:24:46 or came into this. It's like, is it supporting itself? And it's subsidized by other stuff, but like, is it, and are you having fun doing it? Do you find that people drop in just because they wanna meet you and you're upstairs trying to write and you have to contend with that? There is a little of that. I mean, the best part about it was like for the, we basically, we were starting in January and we really didn't open
Starting point is 00:25:14 until late January the following year because it just didn't make sense and we didn't need to. So I just felt from a COVID perspective, like I don't need to force this to happen. So like there was, it was magical to have like 5,000 square feet to myself as I worked on the new book in this enormous bubble for a year. But yeah, people do come in and there are certain days or times where I'm like, I'm up for that. And then a lot of, it also forces me to practice the discipline a little bit because it's like, oh yeah, I could come down and say hi. But if I did that 50 times a day, I would get nothing done. And so I have to be like, no, I'm like, I would like to, but I can't.
Starting point is 00:25:57 I think that's something as we do transition to whatever the new normal is, as we do transition to whatever the new normal is, it's like, I really benefited from the can't of the last year and a half or like shouldn't to the, I could, but I'm not going to. How does that frame how you're making decisions now that the world, the aperture of the world is opening up a little bit? I mean, obviously you have a book coming out.
Starting point is 00:26:24 So you're putting yourself out there and you're gonna do a bunch of stuff. But in general, that calculus of saying yes or saying no has the past year changed how you think about that? Well, it was a very vivid illustration of opportunity costs. So like I, for instance, was under the impression I was pretty productive on the road,
Starting point is 00:26:49 but to then not be on the road, now I have, I just didn't have a control variable. I didn't really ever have evidence of like what the difference was because I would never go long enough without traveling. Like, I don't know about you, but like I in 18, I'd never gone in my life 18 months without getting on an airplane.
Starting point is 00:27:10 Well, and part of the whole reason for living in the part of the world that you live in is it's accessibility to both coasts. Yes. Although also I live in the country because I like living in the country, right? And so yet I was like very rarely there. And so, to be able to write a book where I did no travel,
Starting point is 00:27:31 it was like, not only did I think it's better, but it was easier and faster. So, this book was the least painful of all my books. Because of the lack of distraction. The lack of distraction. And so I was working every single day, which is great, but like I could work, like I felt like I was, I don't wanna say I was working part time,
Starting point is 00:27:59 cause I wasn't, but I was, it was so much more manageable because I wasn't digging myself out of a hole constantly. I was never like playing catch up. And so to have a really clear sense of like, this is what this is costing me. Like every time you say yes to something or saying no to something else and vice versa. And so if it becomes impossible to say yes
Starting point is 00:28:22 to a bunch of stuff, you now have a much better sense of like all the things that you were saying no to. Like, I mean- Or the extent to which your mind will search for other distractions to fill the vacuum. And I'm pretty good about that. I'll start really doubling down on YouTube now.
Starting point is 00:28:39 I'm gonna do a podcast. Although it's like, oh, okay, so you could travel or you could do a podcast from your house. What's a better sort of, what's a less disruptive pursuit? And so I think it was just very illustrative to me of what it was like. So I flew like a couple of weeks ago and I had to do my first in-person talk.
Starting point is 00:29:02 And like, I was trying to work on the plane, like I've always worked on planes. And I was like, I couldn't think at all. And I was like, oh, I must've been pushing through this for the last 10 years of my career. So it's like, it's sort of like when, and I'm sure you- But also working on a plane
Starting point is 00:29:22 was probably more of a necessity because your time was so much more precious in comparison to what it is now. Yeah, and you of all people would know this. Like, you know, when you cut something out of your diet and then you add it back into your diet and you feel disgusting and you're like, oh, but I was eating this every day.
Starting point is 00:29:41 You're like, so it's not new that it's making me feel disgusting. It's that I'd normalized that feeling. You're like, so it's not new that it's making me feel disgusting. It's that I'd normalized that feeling. Yeah, and so to take a whole bunch of stuff away then put it back in, you're like, oh, I was like operating through a fog that clearly had real impact. And it's not that the work wasn't good.
Starting point is 00:30:05 It's that I was having to work extra hard to get to that level. It's like sort of like you're operating with a headwind or something. Yeah, interesting. You were pretty conservative throughout this period. Like you really were at home. Yeah.
Starting point is 00:30:21 You weren't doing anything. Yeah, I mean, I think part of it was like, just the decision to like, it was working. So like, why fix it if it's not broke? But I think a big part, I took it seriously in the sense of like, well, I can just do that. Like, I don't have to send my kids to school. We can homeschool them or I don't have to travel. kids to school. We can homeschool them. Or I don't have to travel.
Starting point is 00:30:45 I can say no to things. And so I did feel like there was some moral obligation and I've been somewhat disappointed with people I know didn't maybe agree with this, but I felt like there was some moral obligation of like, if you can take weight off the system, like you should do it. And so we did it.
Starting point is 00:31:05 And like we, because where we live and how our life is set up, it's like, and everything we needed, we had space. We weren't in a two bedroom apartment in Brooklyn, and so we were like, let's just do this. There's something idyllic about it too, as a young father, this opportunity to spend so much time with your kids in this bucolic kind of environment
Starting point is 00:31:27 of on some level of working ranch, I guess, like I've never visited, but you've got cattle, you've got some livestock, you've got a beautiful home and kind of tending to the land with your children, with your family, while also being a writer, like that's kind of beautiful. It was amazing. It was very privileged of course, but it was wonderful.
Starting point is 00:31:50 And I mean, I'll never get this many consecutive bedtimes in a row. Yeah. I certainly hadn't had them the first four years of my kid's life, but I'll never, I mean, it was like 550 days or something in a row. Yeah, I mean, as a father of older kids, and I'm sure you're already aware of this,
Starting point is 00:32:11 you just become so highly attuned or astutely aware of the fact that parenting is about the grabbing those moments and appreciating the mundane. It's not about crazy trips. It's about that little opening where your kid actually says something to you or confides in you and having that kind of presence of mind to appreciate that. Like now that my kids are for the most part grown,
Starting point is 00:32:42 I mean, our youngest is 14, are for the most part grown, I mean, our youngest is 14. You really like understand how fleeting it all is. Yeah, Jerry Seinfeld had this line that I think about a lot. He was saying like, there's no such thing as quality time. He was like, give me the garbage time. Like 2 a.m. watching TV, eating cereal, like sitting in traffic, doing whatever.
Starting point is 00:33:08 Like as a parent, I think you spend a lot of time being like, yes, let's plan this awesome trip or let's do this thing or I got you this present. You know, like you think about like special things. And I think about that with my own childhood where I was like how stressful it was to go on vacation as if like that wasn't also time. I think about that with my own childhood where I was like how stressful it was to go on vacation as if like that wasn't also time.
Starting point is 00:33:29 You know, it's like- And the pressure that you place upon it to be meaningful or exceptional, that kind of destroys the whole purpose. Yes, it's like, so we're all yelling at each other or the kids are being yelled at so we can all go have a wonderful experience as a family, you know, like no thanks. So like, I think just being together and not
Starting point is 00:33:52 having anything or anywhere to go and that just being very normalized was as financially difficult and emotionally difficult and, you know, like negative in all the ways that it was, was also an incredible gift. And I think we just tried to like stop and go like, why are we rushing through this? We'll never have this again. Stoics are also going like, you know, you're rushing towards death, right?
Starting point is 00:34:19 Like you're, and I thought about that very acutely with kids, like my youngest has now spent more than half of his life in this. Right. And so you're like, well, we want this to be over with. And then you're like, but like, when this is over, that means he's not that this age again. So you're kind of like rushing.
Starting point is 00:34:39 It's like how we try to tell kids, like, you don't wanna grow up. Like, don't rush to grow up. This is great. But as parents, you are doing the grow up. Like, don't rush to grow up. This is great. But as parents, you are doing the exact same thing all the time. Right.
Starting point is 00:34:53 Coming back for more, but first. Okay, back to the show. I want to pivot so that we can start talking about the new book. But I think in preface to that, I've spent a lot of time ruminating on kind of sense-making, how to make sense of our time, this national divide that we find ourselves in,, you know, there's this dispersion of news and information into partisan silos. There's a breakdown from my perspective and healthy communication. And we kind of lost our tether when it comes to rationality,
Starting point is 00:35:40 appreciation for nuance, you know, our sort of respect for one another has been supplanted with binary tribalism. There's an erosion of trust in institutions. Meanwhile, this ascent in conspiratorial thinking, a dearth of leadership where tribalism prevails over virtue, which we're gonna talk about. And we're more interested in taking others down
Starting point is 00:36:04 than rising ourselves up. And I're more interested in taking others down than rising ourselves up. And I wonder how much of that is rooted in this American idea of individualism over community. It seems to be a somewhat uniquely American ethos. And a lot of people who I guess technically can be considered to be behaving quote unquote courageously, but through the lens of their particular strain of perceived truth. Well, we talk a lot about freedom and not very much about responsibility.
Starting point is 00:36:41 And I think, especially in the American system, the whole point of a system that gives or allows for a lot of personal liberty was intended to be checked by private virtue. So just because you can, doesn't mean that you should, or just because it's legal, doesn't mean you should let yourself do it. And so I think we are really struggling as a society and as individuals to wrap our heads around
Starting point is 00:37:18 like where sort of our freedom ends and our responsibility or obligations to other people begins. And that's sort of what I was talking about, where it's like, look, I'm young, I'm healthy. Now I'm vaccinated. I could do whatever I want, or I could have done whatever I wanted despite those things. But like, this isn't, I could make a lot of decisions for,
Starting point is 00:37:42 and we all can, not just related to the pandemic, where the primary recipient of the consequences of those decisions is not born by you. But so it takes some self-awareness and self-control and also courage to be like, I could do that, but that's not a good way to live. but that's not a good way to live. And that's not a fair way to live. And so I think we're struggling with like,
Starting point is 00:38:16 sort of what our obligations are to each other. Like, so people will say with the bookstore, they'll be like, oh, must be great being in Texas, you know, very, you know, sort of conducive to like private, like Texas has been like, do whatever you know, sort of conducive to like private, like Texas has been, um, like do whatever you want as a business. Right. Um, except for some very hypocritical, uh, things that were, they limited businesses, but, um, anyways, like we could have opened, we didn't have to have a mask mandate. We could have done a lot of things,
Starting point is 00:38:42 And we could have done a lot of things, but I actually don't find that to be a gift. I find it to be somebody in elected leadership passing the buck to somebody else. Because somebody ultimately has to decide, hey, am I gonna be part of the problem or am I gonna be part of the solution? So I think that's really where we're struggling. It's just like, here's what I'm allowed to do,
Starting point is 00:39:08 but here's what I allow myself to do per my conscience and my sense of duty and obligations. Right, I think you really nailed it with this idea that all of the focus is on freedom, when in fact freedom needs to be checked by responsibility, right? Like we're not talking about what our collective responsibility is to each other. And we're primarily focused on what we can do
Starting point is 00:39:34 or what my rights are and expressing, however I feel I want to be. And certainly there can be virtue in that. And there's something to be said for understanding that being part of this culture in America is the opportunity to be free. But we all need to shoulder our collective responsibility to each other.
Starting point is 00:39:57 And I feel like we've lost that sense of community. And we have a particular responsibility, the Stokes would say, to the vulnerable and to the less abled and to the people who can't look out for themselves. So like a friend of ours father who was vaccinated, but was also a cancer patient just died of COVID. Like where's that guy's freedom, right?
Starting point is 00:40:28 Somebody took that freedom away from him by their choice to not take a thing seriously, right? Or to not think about the consequences of their actions. And it's the person who touched the person who touched the person who touched the person. But the point is really stopping and thinking like, what am I contributing or taking away from what the Stoics call the common good?
Starting point is 00:40:56 Mark Cyrilius, the emperor of Rome, the most powerful man in the world. Not that Rome was a particularly wonderful place, but he refers to this idea of the common good like 50 or 60 times in meditations. It's like the thing he's constantly thinking about is sort of where, and he's thinking about this during a pandemic,
Starting point is 00:41:14 like what are the choices or actions that I'm taking and how are they impacting the people around me? That the Stoics have this idea of our, they call it the circles of concern. So we have like, first off yourself, then you have your immediate family, then you have like your community and it gets bigger and bigger and bigger
Starting point is 00:41:34 until it's everyone in the world. But the whole idea was like, how do you take the people on the farthest ring and bring them closer to the center? Or how do you take the feelings that you have towards the people that you are biologically related to or genuinely care about? How do you radiate that outwards to as many people as possible? I think it's really easy to be selfish. It's really easy to just think about all the things you have going on and how things affect you. And I think one of the easy to be selfish. It's really easy to just think about all the things you have going on
Starting point is 00:42:05 and how things affect you. And I think one of the things we really spent some time thinking about was like, and it's hard, it was particularly hard not to do that when we watched the sort of racial reckoning that we went through as a country in the summer of 2020 to be like, oh, there's a lot of things that we haven't been thinking about or things that we haven't been thinking about
Starting point is 00:42:26 or people that we haven't been caring about or just problems that haven't affected me that I don't think about, but by not thinking about, I am complicit in their continuation. Yeah, and I suppose the more power that you accumulate, the more ability you have and responsibility that you have to impact those outer rings, right?
Starting point is 00:42:56 Like when you're lacking power, your influence extends not very far to just yourself and perhaps your family, et cetera. But Marcus Aurelius being an extreme example, but anyone who accumulates some level of power, I think the message is that they need to shoulder that responsibility and think more profoundly about the impact of their decisions as those,
Starting point is 00:43:20 as the kind of Venn diagram or these concentric circles. Well, have you noticed or thought, like it's been weird to me to watch people I know with very large platforms just sort of sit a lot of things out. You know what I mean? And there's a balance, of course, because if your platform is based on X
Starting point is 00:43:42 and you're talking about Y, you can lose the reason that people follow you, right? And there's something to be said about being a safe place where everyone can come together and not have to think about certain things. I totally get it. But it is interesting to me to watch the way like certain pet issues, people feel very emphatic
Starting point is 00:44:01 and be happy to use their platform to talk about over and over and over again, which might have a minuscule impact on humanity, but then they don't wanna talk about this because they know it will upset some certain vocal minority. It's complicated. Look, it's hard.
Starting point is 00:44:17 And we are in an environment where if you say the wrong thing, the repercussions are very real. So, you know, I wanna be sensitive to that, but I agree and I understand that. Like it is for a lot of people, a high wire act, like they don't wanna get canceled or they're afraid of, and this goes into courage also, like fear of others
Starting point is 00:44:39 and opinions of other people and being criticized, et cetera. I mean, that was a reason why, of opinions of other people and being criticized, et cetera. I mean, that was a reason why, I went through a little bit of that myself. And that was the reason why we did a pivot with the podcast. And we kind of do this different kind of show every two weeks where we talk about more contemporaneous events, because it did feel weird and not right
Starting point is 00:45:03 to just do, you know, an episode about the microbiome when, you know, like Minneapolis is about to burn to the ground. I just couldn't sleep with myself. So I felt compelled to address these things. But I'm also compassionate to people who are afraid to speak their mind right now, because it is a culture in which we're not very forgiving
Starting point is 00:45:26 of people's transgressions. I mean, I felt like with stoicism, there's a whole bunch of sort of self-improvement elements to it, right? Resiliency, sort of productivity, controlling your emotions. And I could spend my whole life just talking about those things. And those things are much less controversial
Starting point is 00:45:50 than the other things. And I remember just thinking like, that's what good is having the platform if you're only gonna use it to tell people what they wanna hear. There's a story about Lyndon Johnson after he becomes president. This thing he worked for like his whole life, right?
Starting point is 00:46:10 Nobody like moved up the levels of power sort of more like slowly than Lyndon Johnson, right? Like he holds like every consecutive office on his way there. And he spends years as a politician before he eventually becomes president. every consecutive office on his way there. And he spends years as a politician before he eventually becomes president. And suddenly there's this opportunity to pass civil rights.
Starting point is 00:46:31 And, you know, one of his advisors says like, well, we should wait till you're reelected. Or, you know, like this is gonna be negative for the following reasons. And he says something like, but what the hell is the presidency for? Meaning like we tell ourselves like, hey, when I have X, then I'm gonna like use it for good.
Starting point is 00:46:50 But when we never do it, because then we're like thinking about the next thing. And so it's definitely something I've thought about and it pertains to courage too, but it's just ultimately like, what good is the success if it then actually makes you more conservative? And I don't mean that politically,
Starting point is 00:47:07 I mean that in the sense of like, you're now more risk averse because you don't wanna lose what you have. Yeah, well, I've noticed that you're pretty strident about this. Like you'll say something on social media and there'll be a litany of comments saying, I can't believe you said that,
Starting point is 00:47:24 stick to stoicism or how very anti-stoic of you. And then you get in and like, you drag these people. Like- I've tried to actually stop doing that because it was making me unhappy. Yeah, I was like, that part of it, I'm not sure, is in your best interest. But I have noticed, and this is a good segue
Starting point is 00:47:43 into this broader conversation about courage, like to have the courage of your convictions, understanding and knowing beforehand, if you say this, it is gonna provoke a certain kind of reaction that is gonna have ramifications in terms of the number of people who are gonna follow you or buy your books or whatnot. Yeah, it's sort of, again, it's like,
Starting point is 00:48:04 what good is the success if you, it's like that line in the first season of Billions where he says like, what good is fuck you money if you never say fuck you. It's so funny that you say that because I just rewatched the pilot of Billions last night. And so I was thinking, when you were saying that, I was seeing Axe saying that very line.
Starting point is 00:48:27 And I mean, he's using it to like basically enact like to pursue like a personal grudge. So that's not what we're talking about. And he's actually, you know, he's operating at his peril in that moment. Yes, but I generally, we tell ourselves like, hey, when I have this, and I've noticed this, I've gotten to go to Washington a number of times
Starting point is 00:48:46 and talk to people who'd read the books. And like, you think that this Senator is powerful because like they're one of a hundred people and actually they don't see themselves as powerful because they see this as a way station on the way to another thing. And then they say, when I get there, then I'll open it up. Right. But of course they never arrive at that place. You never do. It's insidious. It's in the
Starting point is 00:49:12 same way that you never feel like comfortable or secure. You never go like now I'm willing to like do the unpopular, but correct thing. Right. You, there's many examples in the new book that reference that. The one that comes to mind is, you know, Nixon versus Kennedy in terms of which one of those guys decides to get involved in getting Dr. King out of jail. Nixon, I didn't realize that Nixon had this pretty robust relationship with King. They were friends.
Starting point is 00:49:45 They were buddies and he would call on him for advice. And yet when the moment came for him to act, he was reluctant because he felt he would alienate the South. Kennedy enters and does the right thing and ultimately wins the election by like half a point, right? Yes, almost entirely because of the black community. But you can imagine Nixon telling himself, I'll deal with this after I'm president, right?
Starting point is 00:50:12 He's like, just let me, I don't wanna piss these people. I don't wanna piss off the South. And so I'm not gonna get involved, but I'll do it later. The irony being because he fails in this moment of courage, he doesn't become president. Yeah. And the point being that the thing that seems like the conservative choice ends up being the greater risk. Yeah. And that it, we often understate the risk of doing nothing, right? Like Jeff Bezos talks about, he says, I don't do bet the company bets meaning I don't act conservatively risk averse day to day then you find yourself behind or boring or
Starting point is 00:50:58 lacking in innovation and then you have to bet it all on some moonshot, not literally, but some crazy idea or risky venture, right? If you're regularly innovating and taking risks and being generally courageous in your life, if it's a habit, then it's not as scary. It's only when you have not gotten involved, not gotten involved, not gotten involved, that then to get involved is a huge risk. Yeah, this idea of courage as a habit
Starting point is 00:51:29 and the kind of athletic analogy to that is basically just being consistent, like showing up every day and putting in the training and doing the hard work, not waiting until you're really late in the game and then having to go out and do a 20 mile run when you're ill prepared for it, right? Like you're just gonna get injured.
Starting point is 00:51:48 I think about it just kind of staying at your fighting weight, right? Like when my sort of routine for writing, it's like, I'm just always writing. I'm not writing and then I'm done. Then I go back to my normal life and then I'm intimidated by like going back into. That's really, I think your superpower,
Starting point is 00:52:09 your ability to remain so consistent in your writing. Thank you. I mean, it's either a superpower or an addiction or probably a combination of the two, but I do just generally try to always be doing it so there isn't the sort of whiplash of like on, off, on, off. That's painful. Because it's, if you think too,
Starting point is 00:52:32 there's a great expression, I actually have a chapter about in the book, but I like, it's like the world is a narrow bridge. The important thing is to not be afraid. Meaning like, if you're just walking, you just walk across the narrow bridge. Like you don't think about it, you just have to do it. If you're stopping, resting and looking out over the side
Starting point is 00:52:52 and thinking about it too much, that's when you fall. And so with books, it's like on this project, I'm doing not just one book, I'm doing four books in a four book series. I'm just not thinking about it too much. Like I'm just every day showing up and chipping away at it. And I know that stuff will come out
Starting point is 00:53:12 of the other side of that. But if I'm like, okay, here's the schedule and I have to do this and then this, like that's when I'll start to get in my own head about it. And also knowing what your next three books are gonna be. It's a blessing and a curse. And I would imagine because it's a series on these four virtues in the preparation or the research
Starting point is 00:53:32 for, let's say the next virtue book that you're doing, you're gonna come across research relevant to the third and the fourth book. So you're kind of, are you writing kind of sort of on some level, all four of them at the same time in different of on some level, all four of them at the same time in different stages? I'm researching all four of them at the same time. Actually the hardest part is so obstacle, ego and stillness,
Starting point is 00:53:53 the first trilogy that I did, it was accidental. Like I wrote a book, then independently came up with an idea for a second book and then a third book. So- Now you're operating like Marvel. It's the expanded Ryan Holiday universe. Well, the tricky part is the metaverse of ancient philosophy.
Starting point is 00:54:10 Now that I look at those three books, there's chapters I would like to trade in the books. Like I'd like to move a chapter from ego to stillness and vice versa. Or there's maybe chapters that I shouldn't be in either the three books that would be better in this new series. So like, as I was working on Courage,
Starting point is 00:54:28 it was the first time where I had to go, here's something that's important to me to say. I wanna say it, but do I have the restraint to not say it in this book and leave it for this book? And I've had to, up until all the way through galleys, I was moving chapters around and cutting them and stuff. So it's harder in the sense that I'm having to think in like four projects simultaneously.
Starting point is 00:54:53 And what I can't not be thinking ahead because I might put something in one book that then makes it impossible or either contradicts what I would say in another one or makes it impossible to then talk about that in the third book, let's say. Well, as somebody who's read all your books and is a big fan of your writing,
Starting point is 00:55:16 in reading this book, what struck me is how confident it is. I think it's your most confident book. It's very strident in its directness. It's like a call to action, the whole thing. And I think like in thinking about your previous books, they feel a little bit more kind of observational or cautionary, like don't do this, be careful of this.
Starting point is 00:55:40 This one is very muscular. It's like an active verb. It's very aggressive. And maybe that's a act of courage in and of this, this one is very muscular. It's like an active verb. It's very aggressive. And maybe that's a act of courage in and of itself. But my sense was he's really like found his voice in this vein. And there was no, not that there was hesitation in your earlier books, but it just felt like fully,
Starting point is 00:56:03 like it was very confident and kind of fully formed. Does that make sense? Do you have a sense of that? Yeah, I know it makes sense. I don't know. Cause it's kind of like do this and here's what you're gonna do. And this is the way it's gonna be.
Starting point is 00:56:15 And like, and then it would end with a question like, are you gonna rise to the occasion? And I was like, holy shit. You know, it's fun. This is a weird name drop, but Matthew McConaughey was nice enough to read the book in galley form. He made me get rid of most of the questions.
Starting point is 00:56:31 Oh, he did? He was like, don't, he gave me this really good note. He's like, you're ending on a question as if it is up for discussion. And I was like, oh, that's totally right. Take it off the table. So, so I- I love that you're getting notes from McConaughey.
Starting point is 00:56:43 It was a, it was a surreal, I sent him the book and I was hoping he would give me a blurb because I had blurbed his book. And I was like, and you know, like you can blurb a book without reading it. Like, so I was expecting that. And he gave me like full, like chapter by chapter notes. So it was incredible.
Starting point is 00:57:01 But I do feel like you get to, it was a new feeling on the book where like, I felt like I had all the powers that I needed. Like it had all come together. Like there wasn't any doubt in my mind that I could do it or that I knew what I was talking about or not. It was like the sort of process took over, I guess. Do you know what I mean?
Starting point is 00:57:24 Like in the way that an athlete in like the fourth quarter just sort of goes into a different lane or gear or something that just sort of happened. And I think it was partly the uniqueness of the circumstances of what was happening in the world. And so like, that's something I wanna preserve. But I also think it was just like, I've done this now a lot of times.
Starting point is 00:57:45 And so all of the consciousness of it slipped away and I could just do it. Yeah, it felt like there was no, like whatever you were holding back in earlier books, the floodgates opened up a little bit. Just because I know, I guess- Just because I think, you know, what's sort of unique about your books
Starting point is 00:58:10 is they're sort of genre fluid, like they're philosophical treatises, they're books about history, but they're also self-help books. And I feel like the kind of the self-help vector kind of expanded a little bit in this one. And you were not shy about like being direct in your counsel.
Starting point is 00:58:31 The one thing that the unfair advantage of this book that I will have to find a way to compensate for in the other three books is that courage is like the most primal thing that, like of all the virtues of all the themes of history, of humanity, literature, courage is the most consistent and universal of all the things.
Starting point is 00:59:00 And you're able to draw from the greatest stories of all time. And conversely, when you're talking about cowardice, you're usually drawing on some of the most infamous and shameful moments of all time. And so there is something, there's something magical about that. Well, there's also, there's a kind of masculinity about it
Starting point is 00:59:26 that I think informed the pros. I guess, although that was something I really thought about because we tend to think of courage as physical courage. Right, like, as you said, courage is often seen as a masculine virtue. Although actually in Latin, it's sort of a non-gendered word, like it just is, but like virtue just is.
Starting point is 00:59:51 They're not different for men or women. And in fact, one of the cool things about stoicism is the sort of great stoic teachers, guy, Musonius Rufus, who teaches Marcus Aurelius, sorry, who teaches Epictetus and a bunch of the other great stoics. He's like one of the first philosophers to advocate for like sort of equal training forus and sorry, who teaches Epictetus and a bunch of the other great Stoics. He's like one of the first philosophers to advocate for like sort of equal training for men and women,
Starting point is 01:00:09 basically saying like, it doesn't matter. It's like virtue is virtue. What we do in our lives might be different, but like, he's like, you don't care what the gender of a horse is. Like, does it run fast? That's what matters. Does the dog hunt?
Starting point is 01:00:24 You know, it doesn't matter if it's a male or a female dog. So there is a sort of universality in it, but I did really wanna make it clear and how I picked the stories was a big part of that was like, this isn't just, you know, running into battle or a burning building. Well, of course, men and women both do that, but it's not just physical strength.
Starting point is 01:00:49 That's not what courage is. And that's why I deliberately opened the book with Florence Nightingale as the main character. So it's not war that I'm celebrating, but like the person who is courageous enough and caring enough to focus on like the damage that war does and helping the victims of that tragedy just as much as like the people rushing
Starting point is 01:01:17 into the cavalry charge. We should probably like define our terms and explain what courage is, but the book basically opens with disabusing people of this idea that there are two different kinds of courage, physical and emotional. And yet it is all, in truth, it's one thing. It's when you put your ass on the line.
Starting point is 01:01:34 Mm-hmm. So walk me through like what the four cardinal virtues are, why they're called cardinal virtues and why you decided to write this series of books on this subject matter. Sort of a well-known fact, actually. So I opened the book with this story of the choice of Hercules,
Starting point is 01:01:55 which is Hercules comes to the crossroads and he's basically given the opportunity for the easy way or the hard way, vice and virtue. What does he choose? And he chooses the hard way and this is why it becomes great. But that story is actually, Zeno is the founder of stoicism,
Starting point is 01:02:12 gets in the shipwreck and he loses everything. He washes up in Athens and he walks into a bookstore as the bookseller is reading that story. So the inception, the beginning of stoicism is actually that story, which I opened this book with. And it's a story that I think it goes back to Socrates, but just the idea that we have a choice, easy way, the hard way,
Starting point is 01:02:35 what you can get away with versus what you demand of yourself. And the four cardinal virtues, when people hear the word virtue, they don't really know what that means. And they often think it's like a religious thing, or they think it's like not having fun or something. For the ancients, particularly the Stoics, there were really four virtues, courage, temperance, or self-discipline, justice, and wisdom. And the idea being that any and all situations call for one or all of those virtues,
Starting point is 01:03:11 they all interconnect and kind of check and enhance each other. But when you hear that word cardinal virtue, which is sort of their universal term, they're the stoic virtues, but they're referred to as the cardinal virtues. Cardinal just comes from the Latin word cardos, which means hinge. So the idea is like everything hinges on those four virtues. It's not like a cardinal from the Catholic church.
Starting point is 01:03:34 Yeah, I always assumed that it came from the Vatican. Yes, me too. And then to think, oh no, it predates this by like hundreds of years. Right. And the idea behind, like what got you fascinated in exploring this terrain in book format? I think what I love about the cardinal virtues is that it's as clear as we, it's as close as we get in philosophy to like the 10 commandments, right?
Starting point is 01:04:02 Like so much of philosophy is just sort of vague or general. It doesn't say like, do this, don't do that. And what I really like about the four virtues is it's inherently like, do this, don't do this. Like act with courage, which means don't be a coward, right? Like do the right thing, which means don't do the unjust wrong thing. You know, moderation, temperance just means like nothing in excess.
Starting point is 01:04:28 Also some things not at all. And so to me, what I really wanted to do in this series is sort of explore what each of those virtues mean and sort of in a demonstrable, like memorable way. So going into this book, and sort of in a demonstrable, like memorable way. So going into this book, courage being kind of the preeminent of the virtues, it makes sense to start here. You can't have any of the virtues without courage.
Starting point is 01:04:55 Without courage, of course. We all on some level know what courage is. We practice it, we avoid it, we do all the things. What did you learn that surprised you about courage in this kind of deeper exploration? We think about courage, it's like, we all know what it is. We all admire it. We all know what it can do.
Starting point is 01:05:20 And yet it's relatively rare. Like it's one of those weird things where it's like, we're all in agreement that courage is important. And then we're all sort of looking around being like, why aren't people more courageous? We seem to ask ourselves that question less, right? You know what I mean? We all have strong opinions about the lack of courage
Starting point is 01:05:40 of our elected officials or public figures or whatever. But we're very rarely holding ourselves to the standard that we're asking them. I think what happens is that we look at it and say, well, there's a misalignment of incentives. If the incentives were properly established, then people would be more courageous, but obviously courage means acting in the face of incentives
Starting point is 01:06:10 that perhaps are not aligned in your favor. That is what courage is. Totally, like we'll go like, why won't this politician say what they really think? And we go, oh, they're just worried about pissing off their base. And then it goes to what we were just talking about, which is we go, well, I don't wanna say this
Starting point is 01:06:28 because it will upset my audience. You know, you're like, huh, there's a fun double standard. Right, like we regularly expect other, we go like, why isn't LeBron James speaking out about this? You know, it's because he's afraid of losing his endorsements. And it's like, and you won't tell your boss the truth in the weekly conference call
Starting point is 01:06:50 because you don't wanna get on his bad side. It's just easier not to. Exactly. So we're all doing it on some level. I think the biggest kind of takeaway or epiphany in the most general sense from the book is this idea that courage isn't some trait that we're born with or not,
Starting point is 01:07:07 that it's in fact a practice. Yes. And it's something that we can cultivate through the doing of it. And the commitment to that practice is what of course, you know, breeds a deeper capacity for the doing. Yeah, Aristotle talks about how you acquire the virtues
Starting point is 01:07:24 by doing them, right? Like you become a builder by building stuff. You become courageous by regularly acting with courage in things big and small. And you don't get it by criticizing other people's courage and you don't get it by waiting for some magical moment where like, because it really counts now you'll do it. So as you said, it's like in sports,
Starting point is 01:07:47 like are you consistently doing it in practice? Then you'll probably do it in competition. Are you consistently acting with courage in your life? Then, you know, if you do find yourself in some pivotal world changing moment, maybe you'll measure up to the task. But the idea that you're suddenly going to do it after a lifetime of like the easy road
Starting point is 01:08:08 is probably fooling yourself. Yeah. And we can't talk about courage or the practice of it without fully understanding the impediment to it, which is fear. So the book is broken down into these three sections, fear, then courage, and then heroism. You open with fear because fear is like reckoning with fear,
Starting point is 01:08:31 understanding it, appreciating it, being honest about yourself to the extent that fear, you know, influences your decisions is a predicate upon which, you know, courage can be founded. I didn't say that correctly, but you understand what I mean. There is no courage without fear. Like let's say, and I think there are some people,
Starting point is 01:08:51 it's like a disorder or whatever. Let's say something gets scrambled in your brain and you are no longer capable of feeling fear. As you go through the world, are you being courageous? No, you're probably being reckless, but you're not, the whole point is that you're having to push through the doubts, that you're aware of the danger and doing it anyway, right?
Starting point is 01:09:16 And so fear is both the enemy, but also the opportunity. Like if you don't feel fear, if it's for certain, like if you're starting a business and you know it's guaranteed that you will be successful, like if you could flash forward in the future and know 100% it's gonna work out and there's nothing to regret. There's no courage.
Starting point is 01:09:41 There's no courage. There's no courage. Like it's the fact that it could go either way that makes it impressive, but also makes it meaningful. So help me make sense of the difference between behavior that is provoked by fear, because we're seeing a lot of that right now, a lot of people behaving badly
Starting point is 01:10:01 because they're being motivated by some kind of base fear versus the more noble action of courage in the face of fear. There's a great Faulkner quote where he says like, "'Be scared, you can't help that, but don't be afraid.'" And I like that idea because it ties into what the Stokes talk about, which is like, you're gonna be scared.
Starting point is 01:10:25 This is like a biological thing, right? Like somebody jumps out from the corner, they scare you or you fail. You're gonna be scared by something. There's uncertainty and doubt and newness and emotion. But the question is like, what do you do after? So I think the problem is we have a lot of people who are acting out of fear. They want to either admit that they're scared or they've just
Starting point is 01:10:54 given themselves over to that fear. They've become okay with it. And I think that's the problem. So it's like, you can be angry. Just don't do things out of anger, right? Like somebody hurts you or pisses you off or screws you over. It's totally normal that you would have a negative opinion about that. That stoicism is not becoming this Buddha-like figure where you feel nothing about this,
Starting point is 01:11:20 which isn't fair to Buddha. But you get what I'm saying. It's not, you don't become a robot. It's that you check yourself before you take actions primarily driven by that emotion. Right, here's where courage and temperance overlap in the Venn diagram, right? Totally.
Starting point is 01:11:38 Because just, you know, acting boldly, but reactively isn't necessarily courage and probably isn't. Well, that is the tension between what's bold and what's rash, what's courageous, what's reckless. Right, like being circumspect, understanding the risks, like the Bezos example that you gave. And you see this throughout the book
Starting point is 01:11:59 and the many examples that you offer, including examples of military campaigns, et cetera, where the risks are heavily evaluated, there's still fear. And the decision, the bold decision to move forward is with that awareness. Like the example that you give about MacArthur and Korea, I thought it was pretty instructive on that level. Yeah, he's well aware the odds are not in his favor,
Starting point is 01:12:28 but he's also aware that the odds are not impossible. Right, so just explain that scenario. So when North Korea overruns South Korea, basically the US is sort of caught off guard and MacArthur proposes not just sort of this- He's in charge of that Pacific theater at the time. And he proposes not just like, hey, we're gonna battle them back.
Starting point is 01:12:54 He proposes this sort of bold visionary, like sort of encircling. He basically wants to land troops at Inchon, which is like sort of behind the enemy. And it's an invasion, an amphibious landing that almost everyone is opposed to because success is not certain. And it feels like- And the port is so dangerous,
Starting point is 01:13:17 you can't bring a ship there. It's an incredibly narrow window. It's like at this time on this date, it will work. But if you miss it by 30 minutes, it's a bloodbath. But he actually says, well, this is why it will work. They won't, it's like too crazy for them to expect. There's no one in their right mind to do this. And he says, it basically hits like that line
Starting point is 01:13:38 in Dumb and Dumber where she's, you know, he's like, you're telling me there's a chance, you know? And I think he basically sees that it's not impossible and therefore it is possible. And he believes in his ability to defy the odds, which is, I think, an important part. If you've done things that other people have said are impossible to do,
Starting point is 01:13:58 it does give you confidence in your ability, gives you a certain amount of courage. Like to go to the idea of opening the bookstore, there's I think two parts of this relates to. Number one, as far as risk, of course it's risky. It could fail. But as soon as we decided to take the risk, the next thing we did was like,
Starting point is 01:14:16 well, why do these things typically fail? And how do we de-risk this situation as much as possible? Opening, leasing half of it, starting small. We made a bunch of decisions that took a risky thing and made it less risky. But then also, like I have some confidence in my ability to do it. I don't have blind faith, but I have confidence in it
Starting point is 01:14:38 because I've done risky things before that people said was impossible or was likely to fail. And I have learned from that. And I've also learned from my own capacity and capabilities. So it's like, that is why making courage a habit is important. You're like, oh, I've done a cliff dive like this before. It looks scarier than it actually is.
Starting point is 01:15:07 If you've never done it, then the moment comes and you're totally unfamiliar with something like this. I think it's also important to understand that not all courage is noble, right? Like this idea that you could be technically courageous in your action, but wrong headed. Like I'm thinking about like the occupation of the Capitol, right? All of those people, there's a saying that like,
Starting point is 01:15:31 every man is right from his perspective. So those people would, and the people that support them would say that those are courageous individuals. There's a real risk of death, real risk of consequences. They believe it was the right thing to do. And they are just in their cause from their point of view. But there's an important caveat. And this is the distinction in the book
Starting point is 01:15:54 between courage and the heroic. Lord Byron has a great line. He says, "'Tis the cause makes all that hallows or degrades courage in its fall." So, you know, if you're beating a police officer to death with a Blue Lives Matter flag, like you're taking a real risk, it's a real physical danger,
Starting point is 01:16:19 but it's not just a horrible cause, it's a hypocritical contradictory cause, right? So the decision, I tell the story because I researched it obviously for my first book, or sorry, my first sort of narrative nonfiction book, Conspiracy. I talk about the editors of Gawker resigning on principle over this horrible story that they,
Starting point is 01:16:44 they resigned on principle because the management of the publication had unpublished a story, right? And they felt like this was management crossing an important like church and state line between business and editorial. Now that line is important and it is real, but management was unpublishing a story that outed somebody as gay
Starting point is 01:17:10 who was being extorted by a gay porn star. Like it was a horrible story that should not have been published. So the fact that it was unpublished, while that is morally complicated, the actual principle on the line here is a story that shouldn't have been published. And we see a lot of that, right?
Starting point is 01:17:34 Like one of the examples that really struck me during the summer was, you remember that horrible video of that man at a Black Lives Matters protest in Buffalo. He's like walking up to the police and this police officer shoves him to the ground. And you can hear that thickening or that sickening thud of his head hitting the ground.
Starting point is 01:17:56 Well, that police officer was suspended for that naturally. But then all of the police officers in his unit resigned in solidarity. So yes, the idea of brotherhood or commitment to members of your unit is important. And it takes courage to resign from a career or profession. I don't think they quit their jobs. They just resigned from this one unit. But to do that takes courage. But again, your courage is in service of protecting a person who on video viciously assaulted an old man. So the cause is everything. Courage in pursuit of a crappy goal. I mean, were there brave soldiers who fought for the South? Of course. Were there brave soldiers who fought for Germany or Japan?
Starting point is 01:18:48 Yes. But we instinctively know there's something meaningless about that courage because it was in furtherance of like the worst causes of all time. Right. So deployment of courage in the pursuit of a wrongheaded goal or a sort of ethically compromised aim really confuses the matter because the person who's pursuing that
Starting point is 01:19:18 aim is not under any confusion morally. Well, this is where justice and wisdom act upon courage, right? So if you have fallen prey to misinformation and then feel like what you're pursuing is right, well, it might feel right to you, but you're wrong. And if you, what you're feeling, what you're, you are resisting the power of the state, let's say, or your profession is trying to get you to do something-
Starting point is 01:19:50 At great risk. That you don't wanna do. Yeah, your livelihood. Yeah, that takes courage, but what you're protesting is your right to infect other people with a deadly virus or insert other example, right? Right, QAnon, whatever.
Starting point is 01:20:07 Yeah, you're valiantly defending not just something that's not true, but something that is largely negative or destructive. And so these things all connect with each other in a really important way. Now, is there some room for someone being courageous about something you disagree with? Of course.
Starting point is 01:20:31 And it's hard to definitively say what a good cause is or bad cause. But there is, you know, Lincoln famously goes like, look, the South thinks what they're fighting for is right. But he's like, if you think what is right is stealing the labor and sweat and blood and tears of other people, the South thinks what they're fighting for is right. But he's like, if you think what is right is stealing the labor and sweat and blood and tears of other people, I don't really know what to tell you.
Starting point is 01:20:51 Yeah, I think this gets at the crux of our kind of current cultural moral dilemma because we're seeing the propagation of so much misinformation that is weaponized in many different ways and is now, you know, creating a situation in which it's becoming increasingly difficult to do proper sense-making and to understand what's true and what isn't.
Starting point is 01:21:16 And it's fomenting, you know, tribes of people who are very right-minded in their goals and their aims and are acting courageously. And it's challenging to take a step back and to try to objectively evaluate the landscape from a kind of global umbrella perspective. But ultimately, this is why courage is related to wisdom in that it takes courage to pursue wisdom.
Starting point is 01:21:44 So there's the great poem, The Charge of the Light Brigade, which is the poem about this sort of near suicidal charge by this British cavalry regiment in the Crimean War. And they're basically ordered to attack in a way that was impossible to win over an objective that didn't matter. attack in a way that was impossible to win over an objective that didn't matter. And when you read about it, it's this beautiful, beautiful, inspiring poem. But when you really study the charge of the light brigade, it strikes you that, so they basically go on this suicidal charge and they almost all die. Few of them come back, like 600 leave, like a hundred come back.
Starting point is 01:22:25 And like the men, instead of being angry, instead of being like, what was that? They actually line up to like charge again. Like it was easier for them to just follow orders than to look in the mirror and question the orders, right? So like when we go like, oh yeah, this person on January 6th, or this person who's in this conspiracy theory
Starting point is 01:22:53 or taking this cause, they think that it's right. They also have doubts. Everyone around them is trying to give them the information. And there's this force called cognitive dissonance. The real fear, the real thing that they're being cowardly about is the admission of error or the admission of doubt, right? So like people get in a cult and then the cult does something terrible.
Starting point is 01:23:23 And then none of the predictions of the cult come true. They can't go like, oh man, I was fooled. I was an idiot. The fear is you were wrong all along and the courage then would be to step outside of that and recognize that. Yeah, the scariest thing in the world is admitting you were wrong or that you did something wrong.
Starting point is 01:23:48 And so you can't, the idea of like, oh, they think they're right and they're just pursuing it with courage, shouldn't we admire that? Not only is it like, no, it matters, what are the consequences of the thing you've committed to, but also where they're really lacking the courage is the ability to pause and reflect and analyze
Starting point is 01:24:09 and think about other people. Like what if everyone did this? Stillness is the key. And then recognizing the ego component in all of this, of course, right? This is the extended holiday universe. Yes, this is all the themes coming together. I know, right?
Starting point is 01:24:29 One of the more impactful examples that you share in the book that I admit I didn't know as much about as I should was Charles de Gaulle. Like I didn't realize the extent to which he was this lone holdout and the kind of odds that were stacked up against him saving France.
Starting point is 01:24:50 Yeah, Paul Kicks wrote this great book about the French resistance and this sort of singular figure in the French resistance whose name I'm forgetting, but the book's called the saboteur. But I remember I was talking to him about it as I had him on my podcast. And he said something like,
Starting point is 01:25:05 what percentage of France do you think was involved in the French resistance? And I was like, I don't know, like 20%, 30%. This is like, imagine, it's not like, oh, hey, there's this cause, I'm not sure. The Nazis take over your country, right? Like the worst cause in human history invades your country and occupies it. And like 5% of France was like, this is bad.
Starting point is 01:25:33 We should not go along with this. Like their greatest World War I hero is the one who negotiates the surrender and leads the Vichy state. So, we had this idea in retrospect that like everyone was on the same page. It was all, everyone was heroic, everyone had courage, but it's like demonstrably not the case.
Starting point is 01:25:58 And this is true, like Martin Luther King wasn't a hero. Like we killed Martin Luther King. He was deeply unpopular. It was a small minority of people who saw then what we now perceive today and agree upon. And so, you know, this will be the same for Colin Kaepernick. Again, like for most of these guys, we have to remember they are deeply unpopular.
Starting point is 01:26:25 Yeah, during their time. And De Gaulle was asked, you know, weren't you alone in all the stands that you took? And he says something like, yes, but I knew that one day that would cease to be so. And to me, that's what courage is. The willingness to stand alone and hold out the hope The willingness to stand alone and hold out the hope
Starting point is 01:26:50 that you can rally people around you and make a thing of this. Right, and the theme that emerges from this is this idea, I can't remember exactly the language you use, but the idea of like one courageous person can create that majority. Yeah, one man with courage makes the majority is what the saying is. And it's true, like almost everything
Starting point is 01:27:08 that we now hold to be true was disruptive or controversial or persecuted. And it's, I mean, we didn't throw Galileo a parade. Right, right. And that story you tell about the signing of the declaration, like really like grappling with the peril that those people faced at the prospect of putting their name on this, like, you know,
Starting point is 01:27:34 like document that was so transgressive. Yeah, and I forget which founders said it, but they were reflecting like 40 years after or something they were, because it's also amazing like how young they were. Like they were all like 30 years old. Martin Luther King was like very young in the Montgomery bus boycott.
Starting point is 01:27:52 You know, we think about these figures as we remember them towards the end of their life. They were very young and they had a lot on the line. But one of the founders was reflect, he was like, I'll never forget the awful silence in the room when we walked up one by one to sign But one of the founders was, he was like, I'll never forget the awful silence in the room when we walked up one by one to sign what may well have been our death warrant.
Starting point is 01:28:12 And it's true, like if they were successful, so it wasn't that, but if they had failed, they would have hung like to a man. And I think we miss sight of that in the civil rights movement too. Like not only do we only really tend to recognize the survivors, but like because the cause was ultimately victorious,
Starting point is 01:28:35 we think that everyone who participated got a good deal. We don't think about the sharecropper who, you know, was convinced by some door-to-door civil rights activists to register to vote and then got kicked off their farm. We don't think about the person who was shotgunned on some lonely street. Like I think about that, you know, James Meredith, who integrates, was it University of Mississippi, like the first black person, it's this huge controversy. He's then does this walk. He's like, I'm gonna walk from, I forget where to where, but he's just walking down a highway
Starting point is 01:29:13 and a person drives by and shoots him, like with a shotgun by the side of the road. So we think mostly of the victorious people. We think like, oh, they came out of it the other side, but a lot of people sacrificed a great deal so those survivors could survive. Sure, and that raises the kind of moral dilemma or the moral question of what is right action.
Starting point is 01:29:40 Yeah. Is it better to act courageously and perish as a result of that act or to mute your voice a little bit and live a long life and have kids that love you, et cetera. Like my sense from this book is that one should live courageously.
Starting point is 01:29:58 And if you were to die in the pursuit of that courage, that that is a life well-lived. So where do you fall on that? I mean, at the highest of that courage, that that is a life well lived. Where do you fall on that? I mean, at the highest level, yes, but it's almost seductive how, or it's a little insidious how we think about it that way, as if we don't live in the safest time in human history and are almost never having to risk something like that.
Starting point is 01:30:23 Like I think I had Alexander Vindman on my podcast. Oh, you did? Which was like an incredible conversation. I mean, a single person blows the whistle on a grossly inappropriate conference call with two world leaders and the president is directly impeached as a result of it. But he loses his military career over it.
Starting point is 01:30:43 His brother is fired over it. He loses his quiet, normal life because of it, but he loses his military career over it. His brother is fired over it. He loses his quiet, you know, normal life because of it. But at the same time, he didn't die, right? Like, I mean, there were real risks and I'm sure he feared for his safety, but the point is we, what we're often afraid to lose is like very first world stuff. And he's an immigrant from Russia and went through real stuff. So I'm actually not, that was a bad example to bring up
Starting point is 01:31:09 because that was, he was directly challenging the most powerful person in the world and made a lot of real enemies. But I'm saying like, I remember being so terrified when I dropped out of college. And in retrospect,
Starting point is 01:31:23 it's like the worst case scenario was that I would go back to college, right? Like I'm sure when you left your corporate life to do this, it felt so scary. And it's scary enough that most people don't do it, but it's like how many people would kill for something as dangerous as that? Right.
Starting point is 01:31:43 Well, that goes into how you kind of unpack fear in the first section, this idea that fear comes in many forms, but predominantly fear of what other people are gonna think is a huge driver. I mean, it certainly is for me and kind of catastrophizing what will happen if you make these decisions that hold us back ultimately. And when you really are able to be still, you can understand that the risk perhaps is not as great
Starting point is 01:32:15 as you might suppose. One of the quotes that hit me- But terrifying in the same way, you feel like your life is being threatened. Well, it's clear that like we have strong impulses so we don't like jump off cliffs and die. Like we have that fight or flight life or death reflex. The problem is we apply it to scenarios
Starting point is 01:32:34 that are not nearly so dangerous. And there's a quote from Mark Shabili that I really love. Where we're like, well, what if, what will I do if, like what happens if, and he's just basically like, well, what if, what will I do if like, what happens if, and he's just basically like, you'll meet it with the same weapons that you've met every problem in your entire life. Like, you know, you would like, we think about it. It's like, well, I don't want to get fired, but like, if you quit, you wouldn't be like, what am I going to do? Yeah. Like one is empowering. One is disempowering, you know, but it's the same thing. And so I think we often underestimate or undersell,
Starting point is 01:33:11 like what we bring to the table. Like you'll figure it out. You'll figure it out. You might fail. But our inclination is to wanna know all the steps to get there ahead of time, which obviously keeps us in fear and paralyzed. So you talk about that and that's a very stoic thing. Like the path will be revealed as you take the step.
Starting point is 01:33:39 Fortune favors the bold or the brave and you have to move forward that courage is in action. It is an active verb. It is a practice. And it is in the doing that you cultivate more of it. And in the doing that, you know, the next step will be revealed to you when you need to see it or hear it.
Starting point is 01:33:58 Well, and you can't keep your powder dry forever. And also what would the world look like if everyone was operating under this sort of like, well, all wait and see logic. You know, like, I think that's really a problem. It's like, somebody has to go over the top of the trench. Like somebody has to do it and it's not a fun job, but like, if everyone's like, we'll all be the second,
Starting point is 01:34:20 like all come in and clean up after, then it never happens. And I think this is really where we struggle. Like we have so many issues. I don't even think this is political. We have so many issues as a society that we have to deal with. Climate change, income inequality, like homelessness, like the housing crisis, which is related to home.
Starting point is 01:34:42 We have like so many like intractable, difficult problems that whoever solves will be doing society a good service, but will probably, I don't wanna say it's a kamikaze mission, but it will eat up all your political capital, right? And so people are like, well, if I eat up all my political capital, then I can't run for president or then I can't do this.
Starting point is 01:35:06 And so it's just sort of like, well, what did you get into politics for exactly? Or what did you get into business for? What did you acquire this money fortune platform for? If not to apply it towards problems that need solutions. And so I think we just, we need, to me, that's a really important question. And I think it's Hillel, you know,
Starting point is 01:35:29 it's like, if not me, then who, if not now, then when? Like if everyone just listened to all the reasons not to do it or looked at why the odds were impossible, we would never have progress or change or breakthroughs. Sure, so when you yoke courage to service, service towards something greater than yourself, that's really where heroism comes in, right? This idea, I mean, I just got this book yesterday.
Starting point is 01:36:01 So I did my best to read the whole thing. I got to page 190, which is like right where the heroism chapter starts. But my intuition is that heroism is courage, you know, basically when it's about something greater than one's individual kind of aspirations. It's courage plus, you know, it's like courage when you're not gonna be the recipient of the benefits, right? Like selflessness. And again, it's not always like throwing yourself on a grenade. It can be like, hey, I'm gonna like reduce my margins to pay my workers a fair wage.
Starting point is 01:36:40 I could easily get away with doing it in China at a Uyghur sweatshop, you know, concentration camp, but that's not the right thing to do. So I'm gonna take the hit on that. Right. That's hard. That's really hard. And I think we saw it during the pandemic.
Starting point is 01:36:57 Like, but if I don't do this, sure, I'll be a vector for the virus, but that's bad for business. Is there a tension between like staying in business and the right thing? Of course, but can you on at least a regular basis choose people over profits? Like I tell, like I talk about Reed Hastings,
Starting point is 01:37:22 the courageous decision to jettison the DVD business to- Chairman of Netflix. Yeah, to become a streaming company, immensely courageous. Then you have the streaming company and Hasan Minhaj has a episode about the killing of dissidents in Saudi Arabia. And Saudi Arabia says, take this down. And you're like, okay, you know,
Starting point is 01:37:46 like what good is having a company worth a trillion dollars if you can't stand up for people who get sliced into tiny pieces. I had this very conversation with Brian Fogle who directed the dissident and his struggle to get his incredible documentary platformed on any of these streaming services and none of them would touch it for that very reason.
Starting point is 01:38:12 Even Amazon where Bezos has no love lost for the Prince. I mean, it was his employee. Right. Yeah. So still wouldn't take the movie because they're protecting their base. Right. Because broadening their subscriptions worldwide is more important than somebody's movie
Starting point is 01:38:34 no matter how good it is. Right. But it's not worth the risk. I mean, Bezos would say, well, that's just not a risk worth, like why should I, you know, it's just one movie in my massive enterprise. Right, no, no.
Starting point is 01:38:48 And that's how we excuse moments of cowardice. We always have our reasons. And I don't mean to judge them specifically because to me, what you take from that is like, well, where am I doing this in my own life? That's where we should take from this. But sometimes we use these examples as a way of sort of producing clarity
Starting point is 01:39:05 that we can't see in our own lives. But again, what the hell is the point of being the richest person in the world? If you can't flex occasionally over what's obviously the right thing. Again, we always have reasons why it's not the right thing. But then I can't do this, this or that. But it's usually rooted in,
Starting point is 01:39:26 I don't wanna put up with the consequence. Like I don't want the flack. I mean, he would say it isn't even a function of courage. It's just a risk analysis. Yeah, but at the core of it, what is being risked, right? It's not you're going out of business. It's like slight decrease in profits
Starting point is 01:39:44 or it's a bunch of controversy or it's a giant pain in the ass. This is why we have to really get into what we're afraid of. Like, oh, it's a risk analysis, but what are you risking? Like the risk is nothing. And if you can't, if not you, then who? If you can't afford to risk it, like how can anyone afford to risk anything ever?
Starting point is 01:40:06 Because you of all people need to lead the way for the rest of us. And so throughout all of your books, you're always very careful to kind of avoid current examples because you want these things to stand the test of time, et cetera. But casting your glaze on like our current moment, you mentioned Kaepernick, Vindman,
Starting point is 01:40:26 like who do you look at or see out in the world and say, that person is acting courageously or that person is acting heroically? Yeah, I mean, I think obviously we have a whole bunch of heroes who've done, I mean, even you look at like the 12 or 13 service members who just died in Afghanistan, like they knew that wasn't fun. They signed up for it,
Starting point is 01:40:50 but they went into those crowds to do one of the largest evacuations and rescue operations in human history. I mean, like more than a hundred thousand people were airlifted out in a matter of days, but at immense risk to the people on the ground, right? And so when I think we think about heroism specifically, it's people who like literally
Starting point is 01:41:19 are putting their ass on the line. To me, that's the stuff that we study those, not to be like, oh, you have to enlist, but to be like, again, if they can, if some 22 year old woman, like private in the Marines can walk into a crowd filled with potential suicide bombers to rescue women and children, like you're telling me you can't speak up
Starting point is 01:41:48 about something you saw, or you can't put aside a salary to start your own business. It's too scary. Or like, okay, get up in front of a crowd and talk. Or to see Afghan women in Afghanistan right now in Kabul amidst the chaos of the Taliban occupation continuing to speak out. I mean, the amount of risk,
Starting point is 01:42:11 like real risk that they're taking to do that is just unbelievable. Yeah, or yeah, anytime you're putting your wellbeing second to something bigger than yourself, that's like what gets me going. One of the minor examples I have in the book, I sort of throw away, but it's stuck with me
Starting point is 01:42:31 since I heard about it, is like the decision of like CVS to stop carrying cigarettes or like Chipotle could make more money with crappier ingredients in their food. Like when a business decides to be like, and look, is there a certain amount of marketing to it? Sure, but like, hey, like our commitment to quality or ethics or our people is more important
Starting point is 01:42:54 than like wringing profits out of this part of the business. Patagonia is a great example of that as well. Totally, I love that stuff. And then again- And ultimately it ends up being very much in their self-interest. It usually is, yes. Like in a very outweighed manner.
Starting point is 01:43:13 The irony is that like doing it the shitty conventional way is also boring and not particularly inspiring or cool. And so like the decision to do the, like to make art that everyone else is making is safer, but it's also like probably the least likely to be successful. So going out there, like getting out on a limb, like taking a risk is usually in your self-interest.
Starting point is 01:43:44 So if you have to drill down like the core concepts that you want people to take away from this book, what does that look like? Well, I like the distinction between like being scared and being afraid. Being scared is the immediate reaction. Being afraid is the rationalization or the thing you refuse to do because of that fear.
Starting point is 01:44:06 There's a story I tell in the book that about Theodore Roosevelt and the decision to invite Booker T. Washington to have dinner at the White House. And he talks about how, because he hesitated, like, because he thought for a second, like, what will this mean? Is like why he needed to do it. Steven Pressfield talks about how like resistance is connected to like how important it is. Right. And so if you're not feeling that's probably a sign you're like playing it really safe.
Starting point is 01:44:38 But what's really, what's interesting about Roosevelt is his will to greatness was not, I mean, the Washington example is sort of standalone, but in the context of his presidency, he wasn't a president that faced dire circumstances that compelled him to kind of overcome or rise to the occasion. Like he willed it out of whole cloth
Starting point is 01:45:01 during a period of relative serenity and calm, which makes it to me, like even a more extraordinary capacity for like what he's about. Although the Doris Kearns Goodwin book, a leadership in turbulent times, it's like a great book. She really focuses on the crises of his presidency that I didn't quite know about. I mean, he wins a Nobel peace prize
Starting point is 01:45:22 for negotiating a peace between Russia and Japan, which I didn't really know about. I didn't know. He negotiates like a major strike between the coal mines and the coal workers. He faces down like massive corporate interests in the trust busting stuff. So it's interesting, like, yeah,
Starting point is 01:45:46 we often think like courage is like, hey, we're invaded or- Right, it's grown out of like some circumstance beyond your control compels it. I think it's also though, like the courage to like, not kick the can down the road, you know, like the courage to be like, oh, I'm gonna deal with this problem.
Starting point is 01:46:03 It's not the sexiest problem. It's not the most glamorous problem,, oh, I'm gonna deal with this problem. It's not the sexiest problem. It's not the most glamorous problem, but like, I'm gonna deal. That's another thing in the book too, like owning it, like not shirking responsibility and like understanding that the buck stops with you and kind of being that guy. To me, that's like the impressive thing
Starting point is 01:46:18 with Biden in Afghanistan. And I don't know enough to know whether he executed the withdrawal as well as it could be done. I don't think any of us do. And I don't think enough to know whether he executed the withdrawal as well as it could be done. I don't think any of us do. And I don't think we'll know yet. It doesn't appear that it was executed very well. It does not.
Starting point is 01:46:31 But again, who knows, right? But I think you can put that to the side and go, like this dude gambled his presidency to end a thing that should have been ended a long time ago. Knowing it would be very unpopular and not without its consequences. That's right. And the thing that each one of his predecessors
Starting point is 01:46:53 bore a far higher share of the blame and the responsibility for the poor execution. And so to be like, I'm gonna own this. Like I thought a lot about George Marshall when I was writing the book and I used your dad's book as a source. But you know, his famous thing was like, we're not gonna fight the problem,
Starting point is 01:47:13 we're gonna decide it. Like we're just gonna, we're gonna do something about this. We're not gonna let it be somebody else's problem. That's what leaders have to have the courage to do. Because again, if you're not, just don't be a courage to do. Because again, if you're not, just don't be a leader. Like, I mean, if you're like, hey, I don't, I'm not the kind of person who likes to deal with unpopular, difficult problems. That's totally understandable.
Starting point is 01:47:37 You're not a good fit for being in charge though. Like it's, you know what I mean? No judgment. But it's like, if you're like, I don't like getting up in front of audiences. Okay, don't be an actor or a public speaker. Those are bad jobs for you. You don't have to face everything, but don't pick a job that in which success is entirely dependent on the things you don't like to do.
Starting point is 01:48:04 But also courage is bred through repetition and practice. So putting yourselves in those uncomfortable situations is the opportunity to grow, which is what we're all here to do. So if there is a call to action out of this book, it is to understand that you can cultivate this by taking those tiny steps where the stakes are lower to habituate yourself to this type of behavior.
Starting point is 01:48:30 It's like, how do you think they got good at it? It's like by doing it, by not. Yeah, I mean, the example is always like, Laird Hamilton doesn't drop down on a 50 foot wave, like on day one, he works up to it over decades. Right, right. And it takes courage to tackle it in a small way, but the nice part is that the momentum also builds courage.
Starting point is 01:48:53 I love how you and my dad are like, have this like relationship outside of me. And one of the things that you guys are kind of united on or bond on is this whole thing about like statues. Oh yeah. You know, like my dad is all about like getting this Marshall statue in the Capitol, which looks like it's not going anywhere.
Starting point is 01:49:15 Oh, it's not happening? I don't think it's gonna happen. But to me, that's a big part of it because, and I did a piece, we talked about responsibility earlier. I was talking about, I wrote a piece, we talked about responsibility earlier. I was talking about, I wrote a piece for The Economist about how we need a statue of responsibility. But who we celebrate as our heroes is really important.
Starting point is 01:49:36 Like who we put up on display says a lot about who we are. And it also, I think, has a big impact on who we're going to be. So does our sort of lingering racism and racial issues, is it partly rooted that good chunk of the United States has on its public property celebrations of like people who were instrumental in defending
Starting point is 01:50:09 and propagating those ideas? I do, I think they're related. Conversely, like is our inability to celebrate unifying figures whose courage is not in dispute and who did fight more often than not for just causes. Is that also holding us back preventing us from, is it preventing ample inspiration? Like I think about like, who do I want my kids to like walk
Starting point is 01:50:37 down the street and see me like, oh, that's so-and-so. Like that's a great, you know, a Longfellow says, the lives of all great men remind us we can make our lives sublime. I love the idea of like, who are we celebrating? Like who are our heroes? And I think obviously sort of metal or bronze or marble is like a way to do that.
Starting point is 01:50:59 Conversely, like who are our villains? They should not be celebrated. Yeah, but the way that we define those is very much in flux right now. I mean, certainly, on the one hand, we have people who are defending these statues of Confederate heroes, et cetera. On the other hand, we have people who are calling
Starting point is 01:51:21 for schools to change their name from Abraham Lincoln, you know, and like the battle that, you know, kind of the battle that my dad has been waging over the Marshall thing is that like, you know, Marshall's kind of a racist, you know, because he was a man of that era. And so to what extent do we consider people in the context of their time and celebrate
Starting point is 01:51:46 the great things that they did. And when do we need to pay attention to things that we have for too long kind of persisted in our blind spots over? Well, on the Confederate monument front, which I've thought a lot about, and as someone who's fascinated by the Civil War, one of the things I've explained at like meetings and events and stuff is like,
Starting point is 01:52:04 look, you're saying you don't wanna deny or forget history, that history is important. And I go, I agree. And this statue is not history. This statue is a lie about history, right? There's a Confederate monument down the street from my bookstore in my office
Starting point is 01:52:22 that looks like it is coming down. But- Is that the one you put all this money behind? I did, yeah. It was a whole campaign to get it torn down. And it looks like it'll work. It looks like it's gonna happen, but you never know. But like that statue was put up in 1910, not by grieving widows and orphans
Starting point is 01:52:42 of veterans of the Civil War. By the way, in Bastrop County, it was one of the few counties in Texas to vote against secession. But like that statue was put up like two generations after the war by people who wanted to deny what the war was about. It was a piece of propaganda.
Starting point is 01:53:03 It was a giant middle finger to the federal government. Basically, it was done over the objections, naturally of the black citizens of the county, of course, although it used their money. But it was an attempt to tell a false narrative about history. So removing it is not erasing history. It is allowing the actual history to exist, right? Like the lost cause as we call it
Starting point is 01:53:37 is not like a version of history. It is propaganda. It's a denial. It's an attempt to misinform about the worst thing that Americans have ever done to each other. It's like, hey, remember when we tried to destroy the country and 600,000 people died, because we were not just fighting to defend slavery,
Starting point is 01:54:01 but we're fighting for our right to expand and extend the institution of slavery. The statue was put up generations later to pretend that wasn't the case. Right, I got it. And so as we insist on, like not just the removal of them, but the putting up of, you know, a monument to like where lynchings have happened or signs about what actually happened. We're actually doing the important thing to go
Starting point is 01:54:32 to wisdom. We're having the courage to face the uncomfortable, unpleasant, painful, disturbing, ugly truths of history. And we have to have the courage to do that. I saw a great meme the other day. It was like, if history, like studying history should make you uncomfortable. It should make you sad. It should make you scared. It should make you embarrassed. And if the history you're studying
Starting point is 01:54:57 does not make you feel that, you're probably not studying history. Right, you're studying some propagandized version of history. You're being told what you wanna hear. Yeah, so you know how Tim Ferriss always asks his guests, like if you had a billboard up, like what would you say on the billboard?
Starting point is 01:55:12 Maybe the question for you is, if you had the opportunity to erect a monument in the nation's Capitol, like who would that monument be to or what would be the saying on it? Well, that's my thing. I've talked about New Orleans a lot where I live where I wrote my first book.
Starting point is 01:55:26 So they take down this giant statue of Robert E. Lee in Lee circle, you know, the big monument in the middle of, in the entrance of the French quarter. Well, that was like three years ago, I think, four years ago they did this. And it's like, still stands as just like a 90 foot column in the air, there's nothing there. And it's like how many amazing contributions
Starting point is 01:55:45 to American culture and world culture. Can't we figure out what to replace it with? You can't put a statue of Louis Armstrong there or like I'd rather see a statue of Lil Wayne there than nothing, you know? So like we should be able to decide like who we wanna celebrate. I think if I had to put something, I mean,
Starting point is 01:56:02 I like what I was just writing about was like, we have the statue of Liberty on the East Coast. And I think what the last year has showed us is that we don't really have a liberty problem in this country. If anything, we've got perhaps too much liberty because people think liberty is like, now I can own 15 assault rifles
Starting point is 01:56:21 and not wear a mask or whatever, right? We think we have, liberty is an issue and it's important that we celebrate it and that it be monumentized in world's eyes. But the idea in this, Viktor Frankl actually suggests it in Man's Search for Meaning that the Statue of Liberty be counterbalanced
Starting point is 01:56:42 in San Francisco with a statue of responsibility. And so if I could use my powers or get people to think about anything, it would be that. Yeah, and what would that statue look like? I don't know. Actually, Stephen Covey supposedly put up a good chunk of the money to explore like some designs. And it's like a statue of two arms.
Starting point is 01:57:08 It's like a 90 foot statue of two arms walking like this, which I like, I like the image of that, but I don't know, it strikes me as not. Iconic. Not iconic as the Statue of Liberty. Actually, the funny thing is, the reason I decided to write the piece is that I was reading a book to my kids.
Starting point is 01:57:28 Dave Eggers wrote a children's book called Her Right Foot about the Statue of Liberty. And did you know that actually like her feet, like have you ever looked at the Statue of Liberty's feet? Probably, but I can't. So one of, they're raised, like she's walking. She's not standing. Like when you walk in New York city
Starting point is 01:57:48 and you see like the characters, they're like, you know, that's not what she's doing. She's walking out into the harbor. You can't see her legs because they're obscured by the robes but she's taking a step forward. Yes, not only is she welcoming people into the thing, although the poem comes slightly after is actually part of the crowdfunding campaign.
Starting point is 01:58:12 But like, I think the idea is also that liberty is on the move, right? Like liberty, it's facing the Atlantic ocean, right? Like out into the world. So I like the Atlantic ocean, right? Like out into the world. So I like the idea of, I think the best statues are of people. Although, you know, there's some amazing statues in America or monuments that are not people,
Starting point is 01:58:36 but I would like it to be some sort of embodiment of a physical form of a human. Well, if you're interested in the nation's various monuments and you like looking at graves and cemeteries, you should follow Ryan on Instagram because it's a never ending tour of that. Every time you go out for a run, you never miss a moment to stop,
Starting point is 01:59:00 take a picture of whatever monument you come across and offer some commentary on it. My wife hates doing that. And so- I can see how she'd be like, really? So when you're driving cross country, do you have to pull over every time you see something like that?
Starting point is 01:59:15 Yeah, so like if we get into a new city, my thing is like, I'm gonna go for a run. I'm gonna look at all those things, cross them off the list, have the little moment with them. Do you keep a list? No, I just often am like, oh, the big thing in the city is like this thing.
Starting point is 01:59:28 I wanna see that. And then I don't have to drag the whole family. You truly are, I've said this before, but you truly are a man out of time. I would very much agree with that. You are a member of the great generation at its very, you know, like least modern edge, perhaps like, you would have been well-suited to have been born in,
Starting point is 01:59:50 1904 or something. Although 1904, then your Spanish flu and both world wars and the cold war. But in terms of a shared sensibility. Well, I think what shared is this, I actually think those are timeless things. And it's part of our problem is that we think we're either past certain things or like we look back.
Starting point is 02:00:16 Like, I think I say this in the intro of the book is like, part of the problem with virtue is that we see it as like traditional or old fashioned. And it's like, if it's three or 4,000 years old, it's not old fashioned, it just is. It's part of who we are. It's not like dated, it's dateless. Right, but as postmodernists,
Starting point is 02:00:40 we feel like we've surpassed it or that, not only is it old fashioned, it's anachronistic. You know, we're living in a deeper time of enlightenment where we can't be bothered with something as archaic as that. Well, I think we struggle with, as we have knocked all those things down, we then were like, nothing feels meaningful. Like, I think we are the victims of that.
Starting point is 02:01:06 We are reaping the consequences of like what happens when you tear everything down and you replace it with nothing. And I think that, you know, is one of your copious powers. I mean, you're a great writer, you're a prolific writer, but to me, you're like a living reminder, you know, as a young person
Starting point is 02:01:29 that these things are important and your role or your responsibility as kind of this change agent is to remind people that these things matter. Yeah, I feel like my strength is that I can talk about them in a way that makes them feel not old fashioned and also makes them feel accessible. That's like the trip that I feel like I'm on.
Starting point is 02:01:51 It's like, if you call me a popularizer, you're not hurting my feelings. That's like, you just told me I was successful. The guy who popularized stoicism. There's worse crimes to be accused of. You shared the last time you were here, like you were telling Jordan Harbinger about your new book. And he was like, oh, is this the one where you use examples
Starting point is 02:02:15 from history and ancient philosophy to explain truce? Yeah, that's kind of my jam, man. But it will never go out of style. Hopefully not. Hopefully not. I mean, we'll be in trouble. Solzhenitsyn said, isn't the first sign of the end a decline in courage?
Starting point is 02:02:36 And I think decline in virtue is the prologue of the collapse of not just empires, but like all movements and moments. So it's heady, it's important. Yeah, I mean, the stakes are, I think the stakes are high. Well, it's always a pleasure to talk to you, my friend. It's an honor. Appreciate your wisdom and your perspective on everything.
Starting point is 02:03:01 And I'm at your service. So if there's anything I can do to help you, please reach out and you're always welcome on this podcast. Thank you, I appreciate it. If people wanna reach out and connect with Ryan, you're easy to find at Ryan Holiday everywhere. We didn't even talk about your burgeoning YouTube empire that you're creating.
Starting point is 02:03:20 Ryan's gotten very good at talking to camera and offering advice and wisdom. It's definitely a must follow. So find him on YouTube. You can find him at the Daily Stoic also. Dailystoic.com and at Daily Stoic is where it is everywhere. Which is his robust community on all things stoicism.
Starting point is 02:03:40 And of course, pick up the new book, "'Courage' is Calling," available everywhere. And of course, if you find yourself in Texas, show up uninvited at the Painted Porch bookstore. And I'll pretend to be busy. He may be available, but probably not. All right. Cool man, thanks dude.
Starting point is 02:03:59 Peace. That's it for today. Thank you for listening. I truly hope you enjoyed the conversation. To learn more about today's guest, including links and resources related to everything discussed today, visit the episode page at richroll.com
Starting point is 02:04:19 where you can find the entire podcast archive, as well as podcast merch, my books, Finding Ultra, Voicing Change in the Plant Power Way," as well as the Plant Power Meal Planner at meals.richroll.com. If you'd like to support the podcast, the easiest and most impactful thing you can do is to subscribe to the show on Apple Podcasts,
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Starting point is 02:05:02 special offers on books, the meal planner, and other subjects, please subscribe to our newsletter, which you can find on the footer of any page at richroll.com. Today's show was produced and engineered by Jason Camiolo with additional audio engineering by Cale Curtis. The video edition of the podcast was created by Blake Curtis with assistance by our creative director, Dan Drake. Portraits by Davy Greenberg and Grayson Wilder. Graphic and social media assets, courtesy of Jessica Miranda, Daniel Solis, Dan Drake, and AJ Akpodiete. Thank you, Georgia Whaley, for copywriting and website management. And of course, our theme music was created by Tyler Pyatt, Trapper Pyatt and Harry Mathis. Appreciate the love, love the support. See you back here soon.
Starting point is 02:05:52 Peace, plants. Namaste. Thank you.

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