Finding Courage & Overcoming Fear - Ryan Holiday | Modern Wisdom Podcast 378

Ryan Holiday is a podcaster, marketer and an author. Ryan's next series of books are on the four cardinal virtues of the Stoics with courage being the first and most fundamental. Courage isn't the sort of trait you consider as modern or sexy or massively advantageous when the world isn't at war. But having the ability to overcome your fears is a superpower no matter who you are. Expect to learn how to deal with self doubt in the face of fear, how to overcome social pressure, why Winston Churchill showed the courage of both restraint and aggression during World War 2, how to deal with deliberating about a decision, why the most repeated phrase in the bible should comfort everyone and much more... Sponsors: Get 40% discount on everything from boohooMAN at https://bit.ly/manwisdom (use code MW40) Get 5 days unlimited access to Shortform for free at https://www.shortform.com/modernwisdom (discount automatically applied) Get 20% discount on the highest quality CBD Products from Pure Sport at https://puresportcbd.com/modernwisdom (use code: MW20) Extra Stuff: Buy Courage Is Calling - https://amzn.to/3hWY5uW Check out Ryan's website - http://dailystoic.com/ Get my free Reading List of 100 books to read before you die → https://chriswillx.com/books/ To support me on Patreon (thank you): https://www.patreon.com/modernwisdom #stoicism #ryanholiday #fear - 00:00 Intro 00:39 Moments of Great Courage 11:19 Courage Amidst Unpopularity 17:00 How to React to Fear 28:56 Increasing Your Capacity 34:55 Lessons from Marcus Aurelius 44:56 Growing Through Uncertainty 53:58 Impacts of Being Outspoken 1:01:11 Heroism of James Stockdale 1:05:52 Where to Find Ryan - Listen to all episodes online. Search "Modern Wisdom" on any Podcast App or click here: Apple Podcasts: https://apple.co/2MNqIgw Spotify: https://spoti.fi/2LSimPn Stitcher: https://www.stitcher.com/podcast/modern-wisdom - Get in touch in the comments below or head to... Instagram: https://www.instagram.com/chriswillx Twitter: https://www.twitter.com/chriswillx Email: https://chriswillx.com/contact/

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

• 0:00Ryan Holiday?

  I don't have faith in myself, I have evidence. If you have faith in yourself, you're operating on some false, almost delusional level. False says like, without evidence, I believe. Evidence says like, here's the information that I have to make what I think is a good call, but I could be wrong. Like, when I wrote my first book, I didn't have faith that I could complete it. I had evidence that I completed hard things before, that I had trained for this, that I wasn't a quitter. And so I was willing to make that leap. But the idea that I knew for certain that I would finish, that it would be a success, that I wouldn't regret walking away from a sure thing to do an unsure thing. I mean, that's, that's the whole point.

• 0:42Chris Williamson?

  So I've been watching a lot of the September 11th documentaries, obviously 20th anniversary. And watching that, it genuinely doesn't feel real to me. It's shaken my worldview a lot more than I thought it would, watching it back. I was 12, something at the time. I remember my mom picking me up from school and it was on the radio, but that was kind of it. But yeah, watching that back, it seems insane that that even happened. And then watching it from the perspective of the firefighters and the police officers is ridiculous.

• 1:13Ryan Holiday?

  Yeah, it is. I was a freshman in high school. So I remember being on a, on a, on the West Coast time zone. I remember waking up and it was on the radio and sort of getting the sense that life wouldn't be the same again. I think looking, you know, at it with 20 years distance, I think, especially pertaining to the new book, sort of two, two big themes emerged to me. One was the sort of quiet, ordinary heroism that you're talking about, whether it's firefighters or policemen, or just people who were in the buildings, like working, you know, some people just ran away and some people said, I'm not leaving until I get all of my people out with me. Right? People who had no sort of real legal or professional obligation.

• 1:54Ryan Holiday?

  They were just office colleagues, sort of reacting with extraordinary courage and compassion and, and selflessness. And then I think you contrast that, because I've been thinking a lot about this too. Obviously coincides with the withdrawal from Afghanistan.

• 2:14Ryan Holiday?

  There's sort of two kinds of courage, right? There's the courage that charges ahead into a burning building. But there's also, I think, courage in restraint, in sort of seeing a provocation within its context. And so, you know, the terrible tragedy of 9/11 is not just what happens on that day, but then the immense and mistaken foreign policy that comes after, not just, you know, I think the entrance into Afghanistan makes sense. What we sort of do there over the next 20 years makes a lot less sense. What we do, what the United States does in Iraq, makes almost no sense in retrospect.

• 2:57Ryan Holiday?

  And then, and then you look at the successive presidents and prime ministers who lacked the courage to be able to say like, what the hell are we doing here? What are we spending all this money and this manpower and this energy on? What does this have to do with the tragic events that brought us there in the first place? So in the book, I'm talking about courage. It's not just can you run into a building in the middle of a terrorist attack and save people, although that's really important, but also can you have the courage to both stick with your convictions and question your convictions? Can you, there was an expression about Lyndon Johnson and Vietnam War, that he lacked the

• 3:40Ryan Holiday?

  courage to be seen as a coward, to withdraw from Vietnam, right? And so courage is an immensely complicated topic, but I think 9/11 brings all of its various forms to the forefront, for sure.

• 3:52Chris Williamson?

  There's a Winston Churchill section where weren't people encouraging him to try and go into Germany or to throw all of the forces and he had to show some restraint as well?

• 4:05Ryan Holiday?

  Yeah, so after after France is overrun, the the French are like, we need the entirety of the Royal Air Force and we need it now, right? Like, we can't afford to lose France. And and you couldn't. And yet Churchill knew that this wasn't the decisive moment, that that the real sort of opportunity to drive the Germans back wasn't going to be the British fighting over France. It was going to be the Battle of Britain and and and the British sort of fighting in those dark days over over London and and everywhere else. So, you know, we we we, again, we often think of courage as charging forward, but courage is

• 4:48Ryan Holiday?

  also restraint. Courage is also, you know, holding your fire for the exact right moment. You know, quitting your job takes courage, quitting your job to start a business. But the the moment that you choose to do this is also important, right? You know, did you prepare enough? Are you ready? Is this actually the opportunity to do it? Or is this just the first, you know, the first thing that popped into your head? Actually, I remember I was maybe 22 or 23, but I got my first um, my first book deal. They they came to me and they said, we want you to write a book about Stoicism. And I remember I went to a mentor of mine and I said, you know, this is my dream. This is what I've always

• 5:29Ryan Holiday?

  wanted to do. And I'm ready to go. And he was like, you're not ready. Um, he's like, this book, when you do it, will be better if you wait. And turning that deal down was one of the hardest things that I've ever done. It wasn't a lot of money or anything, but it was just like, that was the thing that I had wanted.

• 5:48Chris Williamson?

  Accolade and status and renown and prestige.

• 5:52Ryan Holiday?

  Oh, I mean, even more than that. It was just the shot that I wanted, right? Like, this was like, I thought this was my one and only shot. And to turn it down was terrifying because, you know, what if it doesn't come back? But the obstacle is the way it came out, probably. Four years after that, and it what my mentor was totally right. I was more prepared. I had a better platform. I was a better writer. The the moment in time was better as well. And so, you know, if I if I had rushed, if I'd sort of courageously pursued the opportunity, I actually would have been worse off than than than the discipline to to sort of check that impulse.

• 6:32Chris Williamson?

  What's the common thread then? If we've got multiple types of courage, we have sort of restraint and bravery.

• 6:38Ryan Holiday?

  Sure. I I to me, I think that the what all forms of courage have in common is it's about putting your ass on the line. So it's about it's about risk, right? If it's a for sure, if it's a guarantee, if there's no danger, you know, we're not talking about courage. That doesn't mean it's not hard. That doesn't mean it's not important, but we're not talking about courage. So there has to be some element of uncertainty or danger or risk to it. Or or there's no courage. And and does that mean that something can be risky and dangerous? And not be be a good idea to do? Absolutely, right?

• 7:21Ryan Holiday?

  It can also be immensely dangerous. You can be successful, but if it's for the wrong thing, you know, is that what we're talking about? No. So so it is a difficult thing to calibrate. And going back all the way to the to the Greeks, the idea of like, where's the fine line between courage and recklessness has always been a long debate. So I don't want to make this seem like it's an obvious thing, or that just like, just because there's risk involved, you should courageously push forward. That that's what the Winston Churchill story is about. There was a moment and then the right moment, and the difference between those two things was everything.

• 7:58Chris Williamson?

  Yeah, it seems like there's a paradigm, isn't there? There's a spectrum between cowardice, recklessness and courage. Is that right?

• 8:06Ryan Holiday?

  Yeah, Aristotle calls this the golden mean and that that courage sits in the middle between those two vices of cowardice and recklessness. There's a great story about a Spartan who's fined for fighting without armor. Like in the midst of this battle, he ripped off armor and he fights like, you know, immensely bravely and and they win. But he's fined for endangering a Spartan asset, right?

• 8:31Chris Williamson?

  Himself.

• 8:32Ryan Holiday?

  He took an unnecessary risk. Yeah. And I think about that. Just because it paid off doesn't mean it was a good idea, right? And and it may have been courageous. It might also have been needlessly stupid.

• 8:45Chris Williamson?

  Yeah, reckless. There's a difference, I think you talk about between, is it bold and rash as well?

• 8:50Ryan Holiday?

  Yeah.

• 8:51Chris Williamson?

  Yeah, same thing.

• 8:52Ryan Holiday?

  Yeah, just just waiting for the right moment is really, is really everything. And and again, this is moral courage and and physical courage, right? You know, don't fire between before you see the whites of their eyes is the expression from the American Revolution. But also, you know, like, let's say you've seen something unethical or you believe that there there's something wrong, like at a company or an industry you're in, you know, just getting up and shouting it at the top of your lungs, that might be the morally correct thing to do. But what and there may be a certain amount of courage to it. But I would argue that the point of it was to stop it from happening. And so being able to identify

• 9:35Ryan Holiday?

  the right moment, or the right plan, or the right sort of strategy to actually make this thing successful, to have the to maximize the impact of what you're trying to do, that also requires courage. So like, the person who just sort of says everything that they think, you know, might might seem courageous, but at a certain point, nobody listens to that person, right? And it's almost, it's almost not courageous, because they never, you know, have to deal with the consequences of their actions. So to to really sort of stop and think about the intersection between courage and self restraint, I think is really important.

• 10:14Chris Williamson?

  And it needs to be filtered through wisdom as well, because if you're deploying it in service of the wrong thing, it's just you're spray spraying it all over the place.

• 10:23Ryan Holiday?

  Or what if, what if you're just fundamentally incorrect, right? So in the US, we have, all over the world, there's a number of people who are vaccine resistant, let's say. But what about the people who are vaccine refusers, right? And does it take courage to sort of risk your job or your reputation to reject this thing? Sure, you're also risking death, but you're fundamentally incorrect, right? So, so I think it's not just wisdom is like sort of how you do it, but what if, what if you're just misinformed, right? And so what you're doing feels courageous and, and there is a certain amount of risk

• 11:07Ryan Holiday?

  to speaking out about it sort of culturally or, you know, financially or whatever. But, but yes, the, the cause ultimately determines whether it, it, it, it matters.

• 11:19Chris Williamson?

  There's some examples from history that you talk about to do with famous, I think it's ex-presidents of the UK or advisor, of the US or advisors who wrote these great books or had these fantastic lives, but then they were incredibly courageous around white supremacy or around discrimination. And it's sort of this very unforgivable type of courage.

• 11:41Ryan Holiday?

  Well, so, so Kennedy famously writes a book called Profiles in Courage, where he writes about a number of politicians who did unpopular, but what he felt like were courageous stans. And one of the stans, he's writing this in the 60s, so about 100 years after the US Civil War, or sorry, he's writing this in the 50s, I guess. So a little less than 100 years after the Civil War. And one of the, one of the things that we, people have often looked at in, in the aftermath of the US Civil War is the impeachment of Andrew Johnson. There's some, so the, the North wins the American Civil War, then Lincoln is assassinated, his vice president succeeds him.

• 12:24Ryan Holiday?

  And he immediately gets sort of bogged down in these political battles over reconstruction. What, what, what rights are we going to give African Americans? How are we going to rebuild, etc. And so Johnson is essentially captured by southern interests and blocks most of the reconstruction agenda. An agenda that today we now see was the right thing, but at the time, you know, tinge with racism was was was not a big priority. But anyways, he gets impeached over some complicated issues that are not really that important to understand, but he gets impeached. But a number of Republican senators block the impeachment, even though their party is the one trying to impeach him.

• 13:08Ryan Holiday?

  So basically, they, Kennedy's view is that this was a brave political stand because they were bucking their own party in defense of the institution of the presidency and blah, blah, blah. Well, a little more distance, we can see a couple of things. So one, they were really, they were really sort of blocking this reconstruction agenda, which in retrospect, the fact that the United States sort of stalled out here is one of our great moral failings, and it's why the civil rights movement has to happen, and it's why we're still reckoning with civil rights today. Andrew Johnson should have been impeached, and if he had been impeached, we probably

• 13:52Ryan Holiday?

  would have been able to heal the wounds of the Civil War earlier. And I know I'm getting way off in the weeds here, but to me, the other second failure, and this is a thing that happens, by blocking the impeachment, it's now like next to impossible to actually get rid of an American president. Like Nixon should have been fully impeached rather than resigning. Clinton probably should have been impeached and removed from office for lying under oath. Trump definitely should have been impeached. So my point is that what Kennedy is looking at, he's seeing this as political courage because they're blocking their political party, they're taking an unpopular stand. But I would actually argue that the real courageous thing would have been to fire the guy over doing the wrong thing.

• 14:36Ryan Holiday?

  And so sometimes what can seem like a courageous stand Because it was risky, you have to zoom out and you have to go, well, what am I really fighting for here, right? What is the cause to which I'm aligned? If I am successful, what am I bringing into the world? And so, like, look, there was, I'm sure there's all sorts of statues to interesting people in Britain who were war heroes. But if we step back and go, well, what was this war about again? It loses some of its luster, right? And I think this is certainly true of the American Civil War. Lots of brave people on both sides. But, you know, when you're fighting for the enslavement of a large portion of your population, it's not so admirable.

• 15:21Ryan Holiday?

  So courage has to be in service of a better world? Well, yeah. So the four virtues, right? And we've been bouncing around. But basically, I'm doing a series now on these four virtues. The first is courage. Why is that the first? Um, well, here, I'll say what they all are, and then I'll say why I put them in this order. So, and this is the historical order. It's not the one I chose. But courage, self-discipline or temperance, then justice, and then wisdom. Now, this dates back pre-Stoics, but is the sort of core ideas that Stoicism is based around. I think courage is first. C.S. Lewis said quite brilliantly that courage is all the virtues at their testing point, right? It's difficult to be self-disciplined in a world of excess without courage. You

• 16:06Ryan Holiday?

  can't pursue justice without courage. Justice without courage is worthless, right? And then to pursue truth, of course, is, I think, the scariest thing of all. So that's the four disciplines. But when we're talking about these, how these virtues intersect with each other, it's really important that you, to realize that you can't separate them, right? So, again, the pursuit of an idea or a concept courageously is good. But if it's not in pursuit of justice, of making the world a better place, or conversely,

• 16:45Ryan Holiday?

  it's in pursuit of injustice, right? That's not a good thing. So, you could be a courageous business person, but if your business is like raping the environment, or you treat your employees really poorly, that's not what this is about.

• 17:02Chris Williamson?

  Yeah, yeah. What's the difference between feeling fear and being afraid? Because it feels like fear is the thing that holds people back from courage.

• 17:11Ryan Holiday?

  Yeah, there's a great Faulkner quote. He says, uh, be scared. You can't help that. Don't be afraid. I think the distinction is fear is or being scared is a natural biological instantaneous reaction. We all have fear, um, but it's about what we do after that. So to me, being afraid is, uh, when fear is made permanent, right? Or when fear is extended into a state of being, right? It's the difference between being angry and doing something out of anger, right? It's okay to be upset by something, but can you keep it under control? And can you make sure that your response is rational and not emotional?

• 17:56Ryan Holiday?

  And, and the Stoics talk about this, like, look, if you jump around, if you jump out from behind a corner and scare me, I'm going to have a reaction, right? That's not, no amount of philosophical training is going to prevent that from happening. But a certain amount of training, in the case of a firefighter or a police officer, as we're talking about, can make it so despite the terror and fear and very real danger, you go into the building instead of away from the building like everyone else.

• 18:25Chris Williamson?

  There's a quote that you use at the start of the chapter that says, "Fear before you're actually in the battle is a normal emotional reaction. It's the last step of preparation, the not knowing. This is where you'll prove you're a good soldier. That first fight, the fight with yourself, will have gone. Then you will be ready to fight the enemy." And that was a British soldier handbook or something.

• 18:46Ryan Holiday?

  Well, I found, I actually found, uh, I found it. I bought a really old rare copy of it because I'd heard the quote somewhere. But basically it, there was a handbook that every soldier in, at least in the US forces, I don't know if it went out to all the allied forces, but I, I suppose it might have. But in, and mine is dated like 1943 and like you can see the name of the soldier in it. Like it's his personal copy. Um, but, but the idea was that, um, they basically. Took all these people who had no training, no experience, they were not lifelong, you know, sort of military figures and they, they, they trained them to go fight in battle and part of that training was this book and they were talking about exactly what we're talking about,

• 19:27Ryan Holiday?

  which is the first battle is not with the enemy, but it's with that internal enemy, your own doubts, your own fear, your own questions. And you have to overcome that to be able to proceed. And I don't think anyone is, again, no one is saying that brave people don't feel those things. In fact, they do. They might even feel them more than you. But what makes them impressive, what they, what they manage to accomplish is what they do in spite of those doubts and fears and worries and dangers.

• 20:00Chris Williamson?

  I like the fact that in that quote, it reminds us that you have challenges that you can control yourself and that by overcoming those, that is the first step on the way to controlling the challenges that are outside of you.

• 20:13Ryan Holiday?

  I would say that and I would also say that it's also the first step collectively, right? So we go like, how do, how do you make an army brave, right? Or how do you make a company brave? Well, there's nothing you can do for everyone else, but you can deal with your doubts and fears and that is contagious. There's a great expression that courage is contagious. So is calmness. So by, by dealing with what you control, which is like, here's what I'm feeling, here's how I'm going to work through what I'm feeling, here's what I'm going to do despite those feelings, that affects not only your own actions, but it ripples through the people around you. You know, panic is also contagious. Doubt is contagious. You know, as we've seen during

• 20:57Ryan Holiday?

  the pandemic, not only is the, is the virus profoundly contagious, but so is, you know, sort of selfish thinking. So are conspiracy theories, right? So is anger. So these emotions are also very contagious and, and when we keep them in check or we, we triumph over them, we are also having a positive impact on the people around us.

• 21:19Chris Williamson?

  How can people overcome fear then? Because it's a very visceral emotion. Like it's

• 21:23Ryan Holiday?

  Sure.

• 21:25Chris Williamson?

  Overpowering.

• 21:27Ryan Holiday?

  Of course, of course. And look, there's obviously different kinds of fear and different levels of fear, but I think we start by like, thinking about it, right? So much of what we fear is just this kind of vague notion, this sort of like, well, what's the worst case scenario? How bad is it going to be? What if I do this? What? We sort of just, our mind races, instead of taking a minute and really thinking about it. The Stoics talk about putting every impression to the test. Sort of, they talk about it, it's like, you know, when you pass like, you spend like a large bill at a, at a, at an establishment, they, they put the, the thing up to the light, or they run the marker over it to see if it's counterfeit. And I think that's something, that's a good analogy when we're thinking

• 22:12Ryan Holiday?

  about courage, is like, is what I'm thinking here based on anything real? Or is it, is it this in my own head? There's a great acronym for fear, False Emotions Appearing Real. And so often, what, what our fears are, have almost no basis in fact or reality, but it's this thing we've made up in our head that feels real.

• 22:37Chris Williamson?

  I couldn't believe that the most repeated phrase in the Bible was to do with fear.

• 22:43Ryan Holiday?

  Yeah, be not afraid.

• 22:45Chris Williamson?

  Do you know how many times it's in there?

• 22:47Ryan Holiday?

  Many times. There's one, one reading of it is that it's in there like more than 365 times, which from what I found is not the case, but, but it's many, many, many times. I mean, I know it appears like a dozen times in the Odyssey as well. It's sort of this, if you think of, and as soon as you think about it, you realize that that's a very common, almost trope in literature, right? It's like, the person is afraid, and then the angel, or a god, or a mentor, or an Obi-Wan, you know, flashback.

• 23:18Chris Williamson?

  Helps them transcend it. Yeah, yeah, yeah.

• 23:19Ryan Holiday?

  Yeah, says, says, you know, don't be afraid, remember your training, or like, don't be afraid, remember what I told you, or like, it's gonna be okay, like, I'm looking out for you, right? So, so that, that is like the constant battle of the human species, which is that we're really afraid of something, but there's a part of us, or a memory, or a, an instructor, or a guide, or whatever that we have, that reminds us that, that we've got this, and that we should proceed.

• 23:49Chris Williamson?

  Does that mean that we have collectively, we have a duty to help other people be courageous?

• 23:58Ryan Holiday?

  I think so. Yeah, I think so. I mean, look, I think the first, the first battle is with your own fear. Right? Like, most of us are called to do something and then we don't do it. Or, or we see something and we go, I don't want to get involved. Or we feel compelled to act or contribute to something and then we go, ah. But like, what if it goes badly? Or what if I get criticized or whatever? Right? So I think our first duty is to our own destiny. Like, am I gonna courageously do what I'm put on this planet? But I do, so I basically, in the book, I sort of split it up. I think first is the battle with fear, then is this triumph over fear, which is courage. But the highest level of courage is when you call courage

• 24:39Ryan Holiday?

  out of the people around you, when you inspire other people to be better, when you make other people better. So I do think we have a duty to make, to, to, to help other people who are faltering in moments of cowardice or fear or whatever. But I, I really feel like you first have to get your own house in order.

• 25:00Chris Williamson?

  Yeah. So after we've stress tested the fear, what comes next? Because there's still times where you don't know you're able to kid yourself into believing that this thing is real. Where did they go next?

• 25:11Ryan Holiday?

  Yeah. I mean, I think that after you sort of battled with this fear, then you, you go. Right? Like you, you take that first step. And I think, you know, it's been interesting, the couple of moments where I've sort of taken big swings in my life, whether it was dropping out of college and leaving my corporate job to become a writer. You're very, you're terrified, right? You're like, this is gonna go so poorly. What about this? What about this? What about this? You know, maybe people you know or care about, in my case, with my parents, I might want to drop out of college. Don't do it. You know, like people trying to actively hold you back. And, but what I, well, the interesting thing is like, once, once it's in motion, Shakespeare talks about how the between, like the consideration and the act is this sort of torture.

• 25:55Ryan Holiday?

  But it's like, once you go, it's, it all falls away. Right? And so I think that's really kind of the next part. It's like, it's just actually, actually doing it. Because once you've done it, you're too busy to be afraid. Right? You're like, dropping out of college, the decision to go into the office and fill out the paperwork, that was terrifying. But immediately after, like now I have to figure out what the hell I'm doing with my life, right? Now I don't have time to think about whether it was the right decision or not, because it's done. So I think that the going is really the next battle.

• 26:29Chris Williamson?

  Those liminal spaces in between are the ones that hurt. I had a neuroscientist on news talking about our brains desire for closure. And this is one of the reasons why when you have missing persons, you know, the nine 11, perfect example, all of the names and faces stapled, it was a thousand people, thousands of people that weren't ever found, bodies not found, no one identified. And it's just that people, they needed to know, even if the news was terrible.

• 26:59Ryan Holiday?

  I think that's right. I mean, I think one of the scariest things in the world is that uncertainty. And this is why we don't make decisions, right? And I have a chapter on this in the book, but, but like, the path, the confidence and courage it takes to make, to say like, I don't have all the information. I don't know if this is the right call or not, but I have enough information that I'm gonna do it, right? Like, there, you know, there's that, there's that expression, and I do like it, it has some value, but that expression of like, it's either hell yes, or hell no, right? That's great, except for I was like 5149 on most of the most important decisions on my life, in my life. But to go

• 27:44Ryan Holiday?

  when you're 100 is easy. To go when you're not sure at all, that's what, that's what courage is about, right? Like, again, we talked, I said this earlier, like, if you know for certain, it's not a big deal. But, but to make, to decide like, hey, I've seen enough, I'm gonna do this. Or, like, yeah, this might, this might blow up in our faces, but we don't have any other choice. Or, you know, hey, as you said with nine 11, like, obviously, it's not 100% confirmed, but like, I have to move, I have to grieve, like, I have to move on with my life. I have to accept this incredibly painful, heartbreaking thing. That, that takes courage, right? It's easier to sit with the uncertainty, or the false

• 28:29Ryan Holiday?

  hope, right? To look reality in the face and go, I don't have a choice. I have to do this difficult thing, like.

• 28:39Ryan Holiday?

  Fear, courage, that's that battle for sure.

• 28:42Chris Williamson?

  I like the idea of stress testing the fears to see if they're real and then committing to action based on what you know. I think that, yeah, taking that first step, as soon as you get through the little liminal doorway, I think that seems to be a good prescription.

• 28:58Ryan Holiday?

  I wrote a piece a couple of years ago and sort of my philosophy, which is like, I don't have faith in myself, I have evidence, right? If you have faith in yourself, you're operating on some false, almost delusional level, right? False says like, without evidence, I believe, right? Evidence says like, here's the information that I have to make what I think is a good call, but I could be wrong, right? Like, when I wrote my first book, I didn't have faith that I could complete it. I had evidence that I completed hard things before, that I had trained for this, that I wasn't a quitter. And so I was willing to make that leap. But the idea that I knew for certain that I would finish, that it would be a success, that I

• 29:42Ryan Holiday?

  wouldn't regret, you know, walking away from a sure thing to do an unsure thing. I mean, that's, that's the whole point. You don't know.

• 29:50Chris Williamson?

  Do you think that could cause people to sell themselves short sometimes?

• 29:53Ryan Holiday?

  How so?

• 29:54Chris Williamson?

  That a lot of the time, we are unaware of our own capacities, that if you are the sort of person who is inclined to downplay your ability, that you may constantly be living with too much being left on the table.

• 30:06Ryan Holiday?

  Well, you do have to be able to step back and see yourself from a distance. Sometimes that means, hey, I'm not as great as I think I am. Other times, it's, oh, like, I may be underselling myself, as you said. One of the reasons that I was confident in the decision I made is that although I didn't quite see it, people that I trusted and admired, who advised me, they did see it. So I had, I was willing to trust their view, perhaps a little bit more than my own. When, when my mentor said, don't write this book, you know, it's too early. Again, same thing. I wanted to do it. I thought I could do it. But I, but I wanted to trust this external assessment more. And, and, and that, that was also a

• 30:50Ryan Holiday?

  bit of a leap as well. So yeah, I, I think it's a tension. So like, if you don't believe you can do something, it's very unlikely that you'll be able to do it. But just because you believe you can do something, doesn't mean you can. So that's the tension, right? If you don't believe you can do it, or if you believe something's impossible, it's impossible for you, right? Like, you're not going to be the one that does it. Um, so that, that, that's, that is the, that is the difficult tension. It's the million dollar question, like, um, you know, whether you've got, whether you've got it.

• 31:25Chris Williamson?

  What am I capable of? Yeah.

• 31:26Ryan Holiday?

  Yeah.

• 31:27Chris Williamson?

  What were the?

• 31:27Ryan Holiday?

  And, and how do you do it on something you've never done before? How do you know on something you've never done before?

• 31:33Chris Williamson?

  This is what I spoke to Seth Goldin about, talking about imposter syndrome. And he said, well, if you're doing something that you haven't done before, by its very nature, you should have imposter syndrome. You're treading untrodden ground. This is trailblazing. This part of the map hasn't been terraced out yet. Like, imposter syndrome comes along for the ride as you break new, new boundaries. Um, I suppose what, what you're saying here is that with the evidence behind you, you should be able to extrapolate forward. Okay. What can I realistically expect to be able to achieve here?

• 32:03Ryan Holiday?

  Yeah. In my ego is the enemy book, I think, uh, I talk about this tension a little bit. So, um, if, if you don't have any doubts, there's probably some ego at play, right? Um, but also if you're consumed by imposter syndrome, like all you're thinking about is like, they're out to get me. They, they think I don't have what it takes. They're whispering about me behind my back. You're probably also exaggerating your importance to other people. Like, nobody gives a shit. They're not thinking about you at all. Right? So, so often the imposter syndrome or the cowardice is like overestimating your importance. Right? So like, people will go like, well, this is really bad. Uh, but I don't want to get involved

• 32:48Ryan Holiday?

  yet because later in the future, I'll be in a position where I have even more influence and then I'll get involved. Uh, or, or they tell themselves, and this was very common with Trump, a lot of the enablers, obviously there was the real toxics or true believers, but there was also the Trump followers who, who considered themselves the adults in the room. Right? And this is actually very similar to Seneca's relationship with Nero. Um, like, I'm very important. I'm a check against the bad impulses of this person. So I might not agree with what they're doing, and I might think that it's wrong. But I'm going to stay here because I'm preventing it from being as bad as it could be. The ego in that is, again, that you're overestimating your importance.

• 33:33Ryan Holiday?

  You're not that important at all. Nobody cares. So ego can sort of trip us up either by making us, you know, sort of unaware of our capacities, or disingenuously overstate our capacities to ourselves.

• 33:48Chris Williamson?

  What would the Spartan temples of fear?

• 33:52Ryan Holiday?

  Um, I, I think the idea is that like you would pay, um, you would pay your respects to fear. Like you would pray to the idea of God as a fear to, uh, to, to know, right? Like that, and I think this is also the point. If you pretend that it doesn't exist, that you don't feel it, you're probably making things more dangerous than sort of respecting it, right? It's like, um, I think, again, we've seen this during the virus. Like people are going like, "I don't want to live my life in fear. You're afraid of it." And it's like, "I'm not afraid of it. I'm just taking it seriously." Right? Because it, it's real and its consequences are real. And you'd have to be an idiot not to, uh, to, to see what it is, right?

• 34:37Ryan Holiday?

  So I, I don't think acknowledging that something is scary or dangerous, or, or that the odds are stacked against you, or that you might not make it out alive, or whatever it is you're facing in the situation, I don't think that's fearful. I think that's actually part of the process of then stepping forward courageously to do what needs to be done.

• 34:58Chris Williamson?

  What about Marcus Aurelius? Is there a particularly courageous moment that you like from your research on him?

• 35:04Ryan Holiday?

  Yeah, I mean, I think just, just the, the, the decision to accept the incredible sort of destiny slash burden that, that's foisted upon him. Um, he's going to be more a character in my book on self-discipline, but... You know, Marcus Aurelius is not born to be the king. He's born to just like an ordinary, uh, upper-class Roman family. And the Emperor Hadrian sees something in him as like a very young man and sort of sets up this process where he eventually becomes emperor. But like, if you had asked Marcus Aurelius, what do you want to do with your life? He probably would have said, anything but be in charge.

• 35:45Ryan Holiday?

  In fact, he weeps, uh, when, when told that, you know, the throne is his, he, he cries. Um, again, the idea that the Stoics don't have any emotions doesn't hold up, but, um, he, he, because he's aware of what a terrible job most kings have done. And he doesn't want to do that. Um, and so I think for Marcus Aurelius, the decision to accept the immensity of the responsibility, you know, you look at like pictures of Obama when he takes office versus when he leaves office.

• 36:15Chris Williamson?

  Fucked.

• 36:15Ryan Holiday?

  And you're like, oh, man.

• 36:16Chris Williamson?

  Fully fucked.

• 36:17Ryan Holiday?

  This job, yeah, this, this job, uh, takes its toll. And so I think, you know, I just a pretty ordinary example for Marcus Aurelius is like, does, he does the hard thing instead of running away from it.

• 36:29Chris Williamson?

  Looking back, do you think he was, do you think he took pleasure or satisfaction from doing what he did?

• 36:37Ryan Holiday?

  I mean, I think he, he came to take a, a lot of pride in being good at it and not, not going the way of his predecessors. But I think he saw it more as of a duty than as a pleasure.

• 36:48Chris Williamson?

  Yeah.

• 36:49Ryan Holiday?

  Yeah.

• 36:49Chris Williamson?

  Yeah.

• 36:49Ryan Holiday?

  There are some people who, you know, are desire power. Um, and you know, occasionally they make good leaders, but I would say more often than not, the best leaders are the ones who want nothing to do with the power or responsibility.

• 37:05Chris Williamson?

  I was thinking about what would happen if everybody in the world was courageous. Do you think it would be too? Chaotic if if everybody was trying to be in the vanguard, do you know what I mean?

• 37:16Ryan Holiday?

  Yeah, it's it's an interesting hypothetical. Um, you know, does does uh there there's an expression, I think it was at Iwo Jima in in talking about, you know, the men raised that that famous flag and someone said, uh, where uncommon valor was common virtue. Basically, like, everyone was courageous, right? Which is extraordinarily rare. You know, if if everyone acted with uncommon valor, would valor then become less valuable?

• 37:43Chris Williamson?

  The Overton window of valor has moved again, yeah.

• 37:46Ryan Holiday?

  Yeah, I probably, uh, but look, you know, we've been recording some version of like our historical epics for 5,000 years. I think the reason that these stories still resonate with us is that it never has been and likely never will be uh common. It it, you know, you you'll you'll hear like a hero will save someone from in front of a train or something and they go, I just did what anyone would have done. And it's like, no, you didn't. Like.

• 38:14Chris Williamson?

  It wouldn't be a big story if anyone would have done that.

• 38:16Ryan Holiday?

  Yeah, right. And and they were you're it's not that you're lying, but you're being, uh, we talked about what you were talking about earlier, you're being um, uh, you're you're selling yourself short because there were other people there when this happened and you were the only one, right? So, uh, I I think it would be a very wonderful champagne problem to have if courage was too ubiquitous.

• 38:38Chris Williamson?

  Yeah, yeah, yeah.

• 38:39Ryan Holiday?

  Um, but but I I suspect that's never gonna be uh, never gonna be the status quo.

• 38:45Chris Williamson?

  What about social pressure? Because that is a big limitation on people being courageous.

• 38:49Ryan Holiday?

  Well, uh, I think thankfully, you know, there's social pressure to be courageous, right? Like, we we hold it up as, I think one of the paradoxes of courage is that we all admire it and then it's rare, right? So like, there and and there have been certain societies versus others that have really prioritized courage, the Spartans, of course, being one. But I I I get your point, which is that, um, often the reason we are not courageous is that we're worried what other people will think. That's probably the most common fear. Um, and the character I used to tell the story is Florence Nightingale in the book. You know, she's born to this immense British family of means, um, doesn't have to do anything.

• 39:31Ryan Holiday?

  She gets called to nursing and her parents are like, we'd rather you be a prostitute. Like, like they're like, this is the worst thing you could possibly do. What will our friends think? And so her battle was not against disease or danger on the battlefield. It was um, against the expectations of what a woman should be doing. It was against the desire of her codependent family. It was, you know, against comfort and against, uh, you know, the status quo and being alone and carving out a new path in life. So.

• 40:06Chris Williamson?

  Didn't she spend like seventeen years in that liminal space that we were talking about?

• 40:11Ryan Holiday?

  Yes, a very, very, very long time. And you could see it as two ways, right? Um, either she's ignoring the call, right? As part of the hero's journey, there's the refusal of the call. And I think that's part of it. But she's also gathering up the determination and the strength and the belief and the skills necessary to do it. So, I mean, to me, that, that it took sixteen years is secondary to the fact that she did it, right? If it, if it took her whole life and she never did it, that'd be a real problem. That it took sixteen years, I'd rather it take sixteen years and then you get a Florence Nightingale out of the other side than, again, she courageously plunges into the fray at

• 40:53Ryan Holiday?

  twenty years old or whatever, but is incapable and, uh, unqualified for the challenge that she embraced.

• 41:04Chris Williamson?

  Isn't it sad that lots of the people who had been the most courageous were alienated when they were alive? And it's sort of only after they're dead that their actions get recognized. So I'm thinking about, like, maybe like a Galileo.

• 41:17Ryan Holiday?

  But that's, that's why courage is so important, right? It's like you're doing it because it's the right thing. Right? Not because you think there'll be a payoff, right? Obviously, you hope. And it would be wonderful if courage was always recognized, if genius was always welcomed. You know, if good deeds never went unpunished. But that's just not how it goes. I think Churchill said that, you know, every prophet has to go through the wilderness. Right? That means the time that you spend away.

• 41:47Ryan Holiday?

  Whether it's forty nights or in his case, almost ten years. But he said it's from this that psychic dynamite is made.

• 41:53Chris Williamson?

  What was the, what was the time in the wilderness for Churchill?

• 41:57Ryan Holiday?

  So Churchill, after the First World War, the failures at Gallipoli and his sort of somewhat out of step political views. Basically, he loses his, his cabinet posts. And then his sort of persona non grata in his political party. And he spends like ten years at Chartwell.

• 42:15Ryan Holiday?

  Basically, a non figure in British political life.

• 42:19Chris Williamson?

  Cool. And then he gets brought back in because they need reinforcements. Yeah.

• 42:24Ryan Holiday?

  And, and the irony is, had he been involved in British political life, the way that he wanted to. He would have been soiled, like he would have been, if not complicit. When, when the British people finally woke up and said. Oh, man, we totally messed up here. Like, we're at war and we're unprepared. They threw the whole government out, right? So he would have been tossed out with the bathwater. So the irony is that by being sent away, he actually had the distance to cultivate. Not just the, the viewpoint that he needed and the, the political base that he needed. But you could also argue, I mean, he was an old man. He was like sixty years old when this happened. So he could have also just retired.

• 43:06Ryan Holiday?

  And so in a way, he gets like a ten year break, like he, he rests. And I'm not sure he would have been able to have the third act of his political life without that, you know, sort of bit of stillness.

• 43:18Chris Williamson?

  Have you heard of Dietrich Bonhoeffer?

• 43:20Ryan Holiday?

  Yeah, he's in the book, for sure.

• 43:22Chris Williamson?

  Sick guy. What a story, man. Like.

• 43:24Ryan Holiday?

  Yes.

• 43:25Chris Williamson?

  Yeah, such a, such an interesting story.

• 43:28Ryan Holiday?

  Very much so, and he's a character in the book. I mean, you know, to me, what I loved about Bonhoeffer is he comes from a wealthy German family. He's opposed to Nazism. He's a Christian pastor. But his family gets him out of Germany in like 1933 or 34. He makes it to New York. Now, he's not Jewish, so he's not like worried about being sent to a concentration camp, but he was an outspoken opponent of Hitler and Nazi politics. So he was a marked man. So he gets sent away. He's free, right? He could have spent the war, as many great figures did, you know, trying to make a difference from exile. But

• 44:12Ryan Holiday?

  he realizes almost immediately that to sit out the war in safety in the United States would be, if not cowardice, it would be contrary to what he felt his Christian duty was. So he gets back on a boat and he goes back to Germany where he sort of actively conspires to assassinate Hitler and is killed for it. But again, I think the assassination attempt and the death are brave, no question. But it takes on a whole kind of transcendent level to realize like he didn't have to do any of it.

• 44:51Chris Williamson?

  And he was dead by 39 or so? I don't think he made it to his 40th birthday.

• 44:55Ryan Holiday?

  Yeah, very young, very young.

• 44:58Chris Williamson?

  Yeah, it's terrifying, man. Thinking about people's fear of growth and change, I think that there's another layer of guilt or shame to it because sometimes we know that there isn't a big line at the door. It's just this sort of very internal battle between us and the new job or the leaving the relationship or the telling your coworker that what they're doing is making you feel bad like that. It's these little things, right?

• 45:26Ryan Holiday?

  Well, in those cases, you're you're still leaving safety behind, right? The safety of silence, the safety of the status quo, the safety of a safety net, right? And the decision to to change, to work on yourself. One of the sort of examples I talk about is like Tiger Woods deciding to reinvent his golf swing. Right? Imagine you're one of the best in the world and you go, ah, but to get to the next level, I have to break down this thing that's working and rebuild it from the ground up, which means I'm going to be bad for a period. That's it. Where you think about Reed Hastings and Netflix. He has a multi-billion dollar business shipping people DVDs, right? And he says, that's not the future.

• 46:11Ryan Holiday?

  I'm going to jettison all of that and become a streaming platform. People don't do that, right? I mean, the reason we talk about businesses being disrupted is because they don't disrupt themselves. What was the story about you at American Apparel? Oh, at the end of the book? Yeah. Yeah, I tell a story at the end of the book about sort of being asked to do something unethical at work. And, you know, I wanted to conclude the book not with a story of like heroism, but like a sort of a more sobering reminder of like how complicated the world is and and how often we we can fall short, myself being no exception of that. And and so I got asked to do this thing and I really struggled with it

• 46:56Ryan Holiday?

  and I decided that it was the wrong thing to do and I wasn't going to do it. But that's like as far as I took it, right? I didn't stop it from happening.

• 47:05Ryan Holiday?

  And I think the reason I didn't stop it from happening is that I didn't want to lose my job. I was willing to risk my job to a certain degree by saying like, that's not for me. Find someone else, but I wasn't willing to. Essentially quit the job or or get fired by actively opposing the thing. And the the irony is, the thing I struggle with looking back at it is like, why did I want to keep a job that by doing the right thing, I would have lost? Right? So that's that's kind of the the strange thing about these moments of cowardice. Right? We're protecting some, we we tell ourselves we're protecting something or someone.

• 47:44Ryan Holiday?

  In fact, we're almost always degrading or risking or damaging the very thing. Right? So again, we tell ourselves, oh, if I leave, then there won't be any other adults in the room. Or we tell ourselves like, but you know, I did, I worked so hard, I shouldn't have to, you know, but it's like, that doesn't age well. And that's part of the reason I wanted to tell the story is that it was morally complex at the time. Right? I was like, well, what about this? And what about this? And what about this? And and there wasn't even any public scrutiny. This was all private. But in retrospect, it doesn't age well at all. You know, it's like, the right thing is obvious. And so it's not that it's in hindsight, it's obvious.

• 48:25Ryan Holiday?

  It's that all my reasons at the time were just sort of short term bullshit that I should have had the courage to be able to see past.

• 48:35Chris Williamson?

  It's the difference between being complicit because of omission and being complicit because of commission.

• 48:42Ryan Holiday?

  Yes.

• 48:42Chris Williamson?

  Yeah.

• 48:43Ryan Holiday?

  Marcus really says, look, you can commit injustice by doing nothing also. Right? And like, so I didn't do the thing. And I don't act that way. And it's not something I approved. And I expressed my disapproval. But it happened anyway.

• 48:59Chris Williamson?

  But you knew the tolerance, right? You knew that not complying probably wouldn't get you fired, but also would give you the get out of jail free card that would make future Ryan perhaps feel less culpable.

• 49:12Ryan Holiday?

  I covered my ass, I risked my ass, but I also covered my ass, right? It's to the, to the perfect balance, right? Um, and, and, and look, it is, it is complicated though, because let's say I had just quit on principle. It probably still would have happened, right? So I would feel better about myself in that sense. But, uh, you know, flash forward three or so years later, I was in a position to hold this person accountable. Uh, and, uh, you know, ended up, um, you know, sort of bringing justice about in that sense. Um, so it's, it, it's complicated, right? It's never a clear cut. Um, and I guess the question is, and this is the, the always the revisionist, what if?

• 49:57Ryan Holiday?

  Is like, perhaps if I had stood up or been more vocal, if this had spurred me earlier, that thing might not have happened three years in the future, but maybe it would have happened one year in the future. Or maybe it would have been brought about in that very moment. So, you know, it's complicated.

• 50:12Chris Williamson?

  How do people not lambast themselves for not being as courageous as they should have been at the time?

• 50:17Ryan Holiday?

  Yeah, it's, uh, it's complicated again. Um, I guess the Stoics would say like, uh, whipping yourself accomplishes nothing. Learning from it makes you better. So for me, I try to think about, and I have tried to think about, um, you know, not like, oh, am I a piece of shit, you know? Am I a hypocrite? Do I, should I, you know, uh, you know, do I need to, uh, how do I punish myself for this? Um, and I try to think more about how can I learn about this, learn from this going forward? How can I identify whatever sort of insidious logic, you know, was, was, was going on in my head at the time? And then also by writing about it, you know, how do I, how do I sort of help people learn from the example as well?

• 51:02Ryan Holiday?

  So, you know, lambasting yourself probably, uh, uh, doesn't move the ball forward much.

• 51:08Chris Williamson?

  Also, I guess focusing on action, as you said, sort of stress testing the ideas and then looking at what's the next step? That's going to help to, um, pattern interrupt the neuroticism. It's going to stop you from doing that. You're too busy actually making a thing happen, hopefully with a little bit more wisdom.

• 51:25Ryan Holiday?

  Well, and sometimes you hear from people who have really dropped the ball or really failed. They're like, I'm a coward. So they actually, they label themselves.

• 51:32Chris Williamson?

  To identify with their own failures, yeah.

• 51:35Ryan Holiday?

  Exactly. It becomes sort of part of the identity and thus makes it even less likely that in the future you'll be able to step up. You want to, ideally, like, when I, when I look at that, I don't see that as like,

• 51:50Ryan Holiday?

  like, proof of who I am. To me, it's me falling short of who I am. Right? So I identify with like the higher self and the lower self was what I did. And the journey and the, the hard work is in getting those closer together.

• 52:06Chris Williamson?

  Is William Tyndale in the book?

• 52:09Ryan Holiday?

  I don't think so. Who's that?

• 52:10Chris Williamson?

  The guy that translated the Bible into English for the first time. So he was, he's a pretty cool story. So he got arrested and executed. But it was originally that the Bible was only ever in Latin because it wasn't supposed to be that the common people in the common parlance were able to read it. And there was sort of this gatekeeping thing going on with the church. You can only access God through us, this sort of bourgeois, yeah, the restriction of access from the normal people.

• 52:37Ryan Holiday?

  Wow. No, no, that, that's fascinating.

• 52:39Chris Williamson?

  Cool guy. Really, really cool guy. Thinking about what you just said there. Is there a responsibility for people who have more power to be more courageous? Because you've got more to lose, but your impact could be greater. But you've worked so hard for 40 years in this company to try and get yourself there. And you're probably more conservative in your values and it's difficult.

• 52:58Ryan Holiday?

  That's really the problem with this idea of like, oh, when I have more power or influence, then I will do it. Because you won't, because actually you have, you'll have a million reasons more in the future not to do it. And this is kind of the tension, you know, we're often surprised when leaders are not courageous. And it's like, well, how long has this person been in public service? 30 years. Well, how do you think they survived a 30-year career in public service? It was by covering their ass instead of risking their ass. So, so the irony is that oftentimes as you work your way up through the, the ranks, you're not becoming more courageous, you're actually becoming less courageous. Because it's filtering out the people who.

• 53:45Ryan Holiday?

  Resist, who stand up, who say unpleasant truths. So I do think there is a higher responsibility, the more influence or power you have. I think about this with my own platform. Are there things that I know that by talking about it will cost me fans or money?

• 54:00Chris Williamson?

  I wanted to dig into that because the last year you've been more outspoken, I think, about some pretty contentious topics, whether that be vaccine hesitancy, whether that be mask mandates, whether that be Trump and stuff like that. And I think you've mentioned it's you've damaged, or at least metric wise objectively, this has hurt, this has hurt your following. Can you just dig into that for me?

• 54:21Ryan Holiday?

  Yeah. To me, so sometimes I'll write something maybe, and I don't actually think that I'm particularly political. I feel like I'm often talking about like sort of basic social contract issues. I'm not like, oh, you know, we need to pass this bill or, you know, I really don't get involved in specific political issues, but I'm just talking about sort of in the, we're talking about justice. I talk about sort of basic issues of justice or fairness or caring about people. But someone will write something, well, why did you have to say this? You must have known it would piss people like me off or something. And I usually reply something, it depends on what kind of mood I'm in. But like, I didn't build a large platform.

• 55:01Ryan Holiday?

  I didn't become a writer to have this microphone to then not say what I think out of fear of offending people. In fact, I got here by saying what I think and I'm going to continue to say what I think because not only is it my moral obligation as a citizen, but it's also my professional obligation as a person who identifies like as a writer. Like to me, the job of a writer is to say unpleasant or unpopular truths, or just to say the truth generally, not to tell people what they want to hear. I tend to find that most of the people who are offended by that stuff are not actually your fans and don't actually matter.

• 55:44Ryan Holiday?

  Like, you know, it's, it's interesting, like I'll, let's say I'll criticize like a Republican president.

• 55:50Ryan Holiday?

  I'll get a bunch of angry emails from random people and then I'll get like emails from actual Republicans in office who'll be like, oh, I liked today's email. That was well said. Like, so, so I tend to find that smart, intelligent people can understand and disagree. It's usually very fragile people who themselves are sort of afraid of being challenged that get the most upset when someone disagrees. But like, one of the, the sort of, one of the things that I try to live by as a person who writes about ideas that are primarily not mine, right? Like, I write about Stoic philosophy. I am not the founder or the creator of Stoic philosophy, right? So if writes about this

• 56:33Ryan Holiday?

  thing, um, who people identify with that, those ideas, then I feel that I have a duty or an obligation to be a good steward of the tradition and the values of the tradition. So could I, would it be more profitable and more pleasant to only talk about, uh, the resiliency side of Stoicism and the productivity side of Stoicism and the courageous fun parts of Stoicism? Yes. Um, but, but to me, that would be neglecting the other, I mean, justice is one of the four virtues. So the idea that I'm not going to talk about it because some people might be triggered by what the Stoics definition of justice is,

• 57:15Ryan Holiday?

  you know, um, that's it. That's just, that's just how it shakes out.

• 57:20Chris Williamson?

  One of the interesting things that I've learned over the last couple of months is how people like yourself and Sam Harris and Eric Weinstein are two other examples of people that do this. They purposefully prune their audience. Uh, they actively go out of their way. They realize that kind of like barnacles on the hull of a ship, that they've picked up some flotsam and jetsam and they kind of need to get rid of it. And they actually go out of their way to self-destruct a little bit. They sort of perform a, um, amputation on a part of themselves. And I think, I actually think that playing chess with cancel culture in this way is

• 57:57Chris Williamson?

  I think you're going to see more of it. Well, maybe you're not going to see more of it because by its very nature, it's quite complex and sort of multifaceted. It's Brazilian Jiu Jitsu lexically. But I got fascinated by it. I really, really did get fascinated because the the show has grown a lot, like tenfold since the last time that you were on.

• 58:14Ryan Holiday?

  Congrats.

• 58:15Chris Williamson?

  Thank you. And I'm like, fucking hell, like, how do I avoid audience capture? Who's actually here for the things that are supposed to be here? And yeah, learning that as a tool, man, like actively going out of your way to say things that you know would trigger the people that you don't want to be there is a really smart tactic.

• 58:35Ryan Holiday?

  I don't know if I'm actively trying to trigger or turn people off, but I think-

• 58:39Chris Williamson?

  Do you think you lean into it a little bit?

• 58:41Ryan Holiday?

  Sometimes, I guess. But I think what I've sort of realized is this, like, and I really noticed this when I started talking about certain things that were getting kind of an unexpected backlash. And what I realized, sort of doing the math, honestly, was that as the books have really, and the different kinds of content that I do has really taken off. A bunch of, like, I thought this was all kind of this small audience and we've grown together. We're all on the same page. And then you realize, actually, no, people heard about you from the algorithm. They heard about you from this article. You know, they got referred. They may have come to you and thought that you were about one thing, when actually you're about the other thing.

• 59:21Ryan Holiday?

  And so you have to be very, audience capture is when you try to be what the audience wants to be as opposed to being who you actually are. Does that make sense?

• 59:32Chris Williamson?

  Yep.

• 59:33Ryan Holiday?

  So what I just try to do is like, who am I? What do I think? What's important to me? That's what I'm going to say. And then as the Stoics talk about, I'm indifferent to whether that gets me more fans or less fans. Right? So I don't care either way. Because what's important to me is that I say what I think is important to the people that I'm trying to communicate with. Right? So I'm not necessarily trying to drive people away, but I'm definitely not not saying things.

• 1:00:03Ryan Holiday?

  Because I'm worried that people will leave.

• 1:00:06Chris Williamson?

  All right.

• 1:00:06Ryan Holiday?

  And if you are worried that people are leaving, not only are you failing them by not telling them what they need to hear, you're also depriving your actual audience of truths that they are equipped to deal with and need to hear. And so it's kind of a double failure.

• 1:00:23Chris Williamson?

  Yeah, you end up trying to be your version of someone else, which means that at the very, very best, you're going to be the second best in the world at whatever you choose to do because you're never going to do what somebody else does better than them.

• 1:00:33Ryan Holiday?

  Yes. And, and look, you're, it's also a risk. It like, people think, oh, it's safer not to do it. But it's also risky to, to not be yourself because eventually you'll get hammered for being complicit, for being silent, um, you know, for ignoring what's happening in the world. I, I think about this with my kids. Like, part of why I talk about what I talk about, I take the stands I want to take is like, my kids are going to ask me in 10 or 20 years, they'll be like, hey, when this thing was happening, what did you do? And I don't want to say, oh, I wrote a lot of self-improvement articles. Do you know what I mean? Like, I, like, I don't want to say, oh, I was really, I was, I was really concerned about growing my email list, so I sort of sat that one out.

• 1:01:10Chris Williamson?

  I created some awesome lead magnets. Yeah.

• 1:01:12Ryan Holiday?

  Yeah, that's not going to age well.

• 1:01:14Chris Williamson?

  Yeah. James Stockdale, that story about him beating himself up and trying to kill himself? Can you tell us that?

• 1:01:21Ryan Holiday?

  Well, he's one of the, the, the great American heroes of the, of the later 20th century and, um, one of the, the sort of last, most famous, sort of explicit students of the Stokes. He reads Epictetus when he's a graduate student at Stanford, which the Navy had sent him to. And shortly thereafter, he gets shot down over Vietnam. And there's sort of two seminal moments in his time. He spends like seven years in this prisoner of war camp, like one of the worst prisoner of war camps in history, a horrible human rights injustice. But, um, like, he's there for like two days and they want him to go on camera and say, you know, everyone's nice here. This is great. And, uh, and so they say, go

• 1:02:04Ryan Holiday?

  into the bathroom and shave, uh, and come back and we'll film this thing. And while he's in the bathroom, he cuts a gash across his forehead. And so he can't, so he can't be filmed. And they, they patch it up and they try to make him go on camera. And anyway, so he grabs a stool and he beats his face to a giant puffy mess. So it's like literally impossible for him to, to film this video. And then later in the camp, um,

• 1:02:30Ryan Holiday?

  Later in the camp, when the torture gets really, really bad, he attempts to kill himself because he's now sort of well-known for being in the camp. And he attempts to kill himself sort of in an act of defiance and protest of the torture. So it's not that he's killing himself to escape the torture. He's making a statement or a sort of a public challenge to the captors that would have publicly embarrassed them to a degree that, you know, might have massively escalated the war effort. So in these sort of two moments, he puts his physical appearance, safety, well-being, and then even his life on the line to protect both his duty to his country and then also to his fellow prisoners.

• 1:03:15Chris Williamson?

  That's the transcending, that's the heroic element of courage, right?

• 1:03:20Ryan Holiday?

  Yeah, look, the courage to start your own business is real, right? I talk about Michael Jordan, Michael Jordan leaving basketball to play minor league baseball. Courageous, scary, terrifying, really interesting. Maya Moore walking away from the WNBA to get a man wrongly convicted out of prison, you know, is a different level of courage and selflessness, right? She's risking it, but she doesn't get the benefit of it. She's not risking it because she wants to go play baseball. She's risking it because she can't live with herself if this guy, you know, spends one more day unnecessarily in jail.

• 1:04:02Chris Williamson?

  What's the best James Stockdale book? Because every time that I read something of yours, he gets brought up, but I don't know what to read.

• 1:04:07Ryan Holiday?

  He wrote a number of like little short books. There's unfortunately not a great biography of him, but he has a short book called Courage Under Fire that's sort of about Stoicism and his time in that prison camp. And then Jim Collins talks about him a lot in Good to Great as well.

• 1:04:25Chris Williamson?

  Hmm. Someone should do that. Someone should put all of that together. Somebody that's someone that's listening. Have you read Alistair Ercart's The Forgotten Highlander? Oh, dude.

• 1:04:36Ryan Holiday?

  I'll write this down.

• 1:04:37Chris Williamson?

  Bro, this is, this is the most Ryan Holiday book that I can think of. So this guy who is in the The Forgotten Highlander by Alistair Ercart, Scottish regiment, working in, I want to say Singapore, when Vietnam go to war with America.

• 1:04:55Ryan Holiday?

  Yeah.

• 1:04:55Chris Williamson?

  Gets captured by, when Japan go to war with America, gets captured by the Japanese, builds the bridge over the River Kwai, gets put in a forced labour camp for basically four years, constantly has dysentery and every tropical disease under the sun, gets locked on one of these hell ships, which is a tin box with no food or water out at sea in 40 degree heat for a month. Then he gets knocked off his feet by the Nagasaki bomb blast as he's working 30 miles from it, stays silent for 50 years because the army told him to, and then finally writes this memoir as a call to account for the Japanese for the atrocities that they've gone through. It's one of my top 10 all time favourite books. It's outstanding.

• 1:05:38Ryan Holiday?

  Well, I wrote this down and I'm going to look up William Tyndale as well.

• 1:05:41Chris Williamson?

  Sick. Well, look, Ryan, man, courage is very much needed, it seems like at the moment in the 21st century, and we are in short supply. Courage is calling will be linked in the show notes below. Where should people go to keep up to date with the other stuff that you do?

• 1:05:56Ryan Holiday?

  I do an email totally for free about Stoicism every single day, dailystoic.com and at Daily Stoic and at Ryan Holiday on pretty much every platform.

• 1:06:07Chris Williamson?

  I love it, man. Until next time.

• 1:06:08Ryan Holiday?

  Thanks. Congrats on the growth.

• 1:06:10Chris Williamson?

  Thank you, man.