6 Stoic Rules To Beat Ego

You don’t need to be an egotistical asshole to be successful. History is filled with powerful people whose pride ultimately destroyed them, from Caligula and Nero to Xerxes and Mussolini. The Stoics believed the antidote to ego was humility, self-awareness, reflection, and honest introspection. In this episode, Ryan explores the dangers of ego and the timeless practices that can help you keep it in check, stay grounded, and remain a good person as you become more successful. Featured Guests: Fighter Pilot Michelle Curran https://www.youtube.com/watch?v=sN5FBB5Y8Ms | Full episode on Spotify https://open.spotify.com/episode/0rQaOH06Me5DfaycRJG5LK, Apple Podcasts https://podcasts.apple.com/br/podcast/the-day-my-ego-almost-killed-me-fighter-pilot/id1430315931?i=1000725849863, YouTube https://www.youtube.com/watch?v=sN5FBB5Y8Ms Helen Lewis - author of The Genius Myth https://podcasts.apple.com/fi/podcast/the-fine-line-between-genius-and-delusion/id1430315931?i=1000740592431| Full episode on Spotify https://open.spotify.com/episode/6Gx7w4kGALXzDVIkrRvAzQ, Apple Podcasts https://podcasts.apple.com/fi/podcast/the-fine-line-between-genius-and-delusion/id1430315931?i=1000740592431 Lamb of God lead singer Randy Blythe https://www.youtube.com/watch?v=M_JNtgzPTLE | Full episode on Spotify https://open.spotify.com/episode/5NEMuz2qc9fbnUFtRjZIzV, Apple Podcasts https://podcasts.apple.com/us/podcast/lamb-of-gods-randy-blythe-on-conquering-inner-demons/id1430315931?i=1000691221119, YouTube https://www.youtube.com/watch?v=M_JNtgzPTLE Comedian Chad Goes Deep https://podcasts.apple.com/ug/podcast/stop-taking-yourself-so-seriously-chad-goes-deep/id1430315931?i=1000724131306 | Full episode on Spotify https://open.spotify.com/episode/7I2xOuvNDcwyrjavrZOal2, Apple Podcasts https://podcasts.apple.com/ug/podcast/stop-taking-yourself-so-seriously-chad-goes-deep/id1430315931?i=1000724131306, YouTube https://www.youtube.com/watch?v=5WfcfrtAuGI Seth Wickersham - Senior Writer at ESPN https://podcasts.apple.com/us/podcast/the-heaviest-crown-in-america-the-quarterbacks/id1430315931?i=1000727156105| Full episode on Spotify https://open.spotify.com/episode/5Aa2lbJt8VR1rQ21GUQv8s, Apple Podcasts https://podcasts.apple.com/us/podcast/the-heaviest-crown-in-america-the-quarterbacks/id1430315931?i=1000727156105, YouTube https://www.youtube.com/watch?v=mq_JzyzZpY8 🎥 VIDEO EPISODE https://www.youtube.com/watch?v=zhibdimmh7s| Watch this episode here https://www.youtube.com/watch?v=zhibdimmh7s: https://www.youtube.com/watch?v=zhibdimmh7s 🎟️ DAILY STOIC LIVE https://www.dailystoiclive.com/| Ryan Holiday is coming to a city near you https://www.dailystoiclive.com/! Grab tickets here https://www.dailystoiclive.com/ | https://www.dailystoiclive.com/ ✉️ FREE STOIC WISDOM https://dailystoic.com/dailyemail | Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemail https://dailystoic.com/dailyemail See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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

• 0:00Ryan Holiday?

  Welcome to the Daily Stoic Podcast, designed to help bring those four key Stoic virtues, courage, discipline, justice, and wisdom into the real world.

• 0:15Ryan Holiday?

  You don't need to be an egotistical asshole to be successful. Are there a lot of egotistical assholes who are successful? Sure, but there's also quite a few catastrophic failures who were Caligula, Nero, Xerxes, Mussolini, and then, of course, business and art and entertainment show us the truth of the old Greek saying that whom the gods wish to destroy, they first make proud. And so for the Stoics, the antidote to this was humility, was self-awareness, was introspection, was reflection. And that's what we're going to talk about in today's episode. Not just the dangers of ego, but timeless practices that help sweep it away, that help you get clean and stay good.

• 1:03Speaker 01

  My first squadron, there was a lot of jockeying for position with the young pilots, the lieutenants, the captains. You're friends with everyone. Like, you trust that person with your life, super tight knit, but you're also very aware of how everyone's doing. You don't want to be made to look bad. And I think a lot of it is like, you feel like you're really establishing your reputation in this career field you're going to be in for a decade.

• 1:24Ryan Holiday?

  Yeah.

• 1:25Speaker 01

  And you don't want to look incompetent. And for me, for a long time, I thought I was like, I was like too humble, like I wasn't boisterous. I wasn't loud. I wasn't type A. And I felt like I had a hard time fitting in in that culture.

• 1:37Ryan Holiday?

  Yeah.

• 1:37Speaker 01

  But in hindsight, I realized that my ego was actually getting in the way because I saw asking questions, asking for help, letting people know I was struggling with a concept in the airplane as weakness.

• 1:49Ryan Holiday?

  Yeah.

• 1:50Speaker 01

  And I felt like I could not show weakness in that environment.

• 1:52Ryan Holiday?

  Yeah, there's an ego. People don't think about it this way, but there's an ego even in that kind of imposter syndrome or that sort of wallflower-ness where you just think people are thinking about you way more than they are. And that these things say more about you than they do. And so, yeah, because you don't want to look stupid, you'll stay stupid. Or because you don't want to ask for help, you don't get help. Or you don't want to look like you want it too badly, so you don't get it. It's this weird thing where, yeah, the person who needs to be the center of attention, they make everything about them. That's a very obvious and harmful form of ego. But then we have this other form of ego that maybe we convince ourselves is humility or self-awareness or something,

• 2:37Ryan Holiday?

  but it's actually just a similar self-absorption.

• 2:40Speaker 01

  Yeah, my whole world revolved around me in that I felt like everyone was watching every little thing that I did. And so I was hyper vigilant about how I reacted to people's comment. And part of this, I don't think you can not talk about gender being layered in there, right? I'm like one of two women in a squadron of 50 pilots.

• 2:58Ryan Holiday?

  Yeah.

• 2:58Speaker 01

  And there's a lot of like nuances of, oh, they said it in an appropriate joke. Everyone looks at me and waits for my reaction.

• 3:04Ryan Holiday?

  Yeah.

• 3:05Speaker 01

  And I felt the responsibility of that. And also, if I'm bad at something, now there's a stereotype that female fighter pilots are bad at this thing. I'm a data point of one.

• 3:13Ryan Holiday?

  Mm-hmm. You're just spending too much time thinking about what other people are thinking. And you don't realize that the cost of that is thinking about things that you actually have some semblance of control over or would make a difference. You're just like, what are the critics going to say? How's this going to go? Do they like me? Did that come off weird? And yeah, what you're not thinking about is like flight semantics, schematics, or whatever.

• 3:35Speaker 01

  It's a massive distraction.

• 3:36Ryan Holiday?

  Fearlessness, and then you would say ego. Both of them are somewhat adaptive at the beginning of things. Because ego makes you go out for things that you have no business going out for. And so in the beginning, it's an advantage, or at least it's not as costly as it becomes later. But it's a real bad habit to pick up in both cases, I feel like.

• 3:55Speaker 01

  Not being afraid of things you should be afraid of.

• 3:57Ryan Holiday?

  Yeah, right.

• 3:58Speaker 01

  Like, you will not be an old fighter pilot with that mentality.

• 4:02Ryan Holiday?

  Especially when you're having to stand out in a field, you know, or you're having to get past a lot of reservations or resistance. All that can kind of work to your advantage. And then you get there, and now you're an asshole. Or, you know, now you think you're exempt, or you've made a bunch of enemies. Or again, yeah, you've picked up really bad habits and you don't have the kind of sound fundamentals, which should be like self-awareness, empathy, et cetera. You know, a sense of caution and prudence. And now, even though it got you where you wanted, whether it's a fighter pilot or a record deal or a successful business, the irony is, it gets you what you want, and now the stakes are much higher. So you're going to be learning these painful lessons,

• 4:47Ryan Holiday?

  like the cost of fearlessness or ego. And now you're doing it in the air instead of in a simulator, or you're doing it with something to lose, like all that you've built. And that's why they say pride goeth before the fall. At what level do you want that fall to happen?

• 5:04Speaker 01

  I think our safety net for that, because the what got you there, if you are very overly confident, if you are hangman from Top Gun Maverick, that can get you places initially.

• 5:16Ryan Holiday?

  Yeah.

• 5:17Speaker 01

  But that debrief at the end of the flight and the way that's structured and the humility required in there, like every little thing you did wrong in the air is picked apart.

• 5:26Ryan Holiday?

  Yeah.

• 5:26Speaker 01

  And not in like this ridicule, shame you way, but in like, okay, you were late to that. Why were you late? What were you thinking about? Did you have the wrong information? Or did you have the right information to make a wrong decision? Like, we just peel back the things until we're like, oh, here's the root cause of why we failed at our mission.

• 5:41Ryan Holiday?

  Yeah.

• 5:42Speaker 01

  And no one is spared from being criticized. And we actually have language in our grade sheets. Like, when you're an instructor and you're teaching someone new and they're just pushing back, you're like, hey, you didn't do this like you were supposed to. What happened? And they will come up with excuses, not reasons, but excuses, right? They won't take ownership of it. They won't walk away with, okay, next time I'm going to do this better.

• 6:01Ryan Holiday?

  Yeah.

• 6:02Speaker 01

  It's just failure to take instruction.

• 6:03Ryan Holiday?

  Yeah.

• 6:04Speaker 01

  And people can get kicked out of programs or even out of the jet and move to a different career field if they just continue to, because it's dangerous.

• 6:12Ryan Holiday?

  Yeah.

• 6:17Ryan Holiday?

  Behind me is an enormous mausoleum, built by and for one of the most powerful men in history, a man of enormous ego and enormous vanity. Hadrian, when he had this built in 139 AD, he said to his architect, "Make it bigger and more impressive than Augustus's." And indeed, it rivals not just Augustus, but it rivals some of the Egyptian pharaohs. And it held not just Hadrian's remains, but that of his successors too, Antoninus and Marcus Aurelius himself. But Marcus Aurelius would have found this to be the antithesis of Stoic philosophy. He actually addresses it in Meditations. He says, "Consider that before long, you'll be nobody, just like Hadrian, just like Augustus." He said, "So live and act with humility."

• 7:01Ryan Holiday?

  Now, you might think the fact that this is still here 2,000 years later, that it's a museum, that it has endured through all these centuries, that it might disprove Marcus's point. But actually, it doesn't, because you know what happened? In 400 AD, Rome was sacked by the Goths. And they broke into the temple and they scattered the ashes everywhere. We have no idea where they are. They were lost to the ages, which is also something Marcus Aurelius talks about in Meditations. He says, "Alexander the Great and his mule driver, they both died, and the same thing happened to both." And indeed, the same thing happened to Augustus. We have no idea where his body is. The same thing happened to Hadrian. The same thing happened to Antoninus. The same thing happened to Marcus Aurelius. And the very same thing will happen to you.

• 7:45Ryan Holiday?

  He's saying, you know, ego is the enemy. Live with humility. Remember, you are not immortal. You are not a god. You are not special. You cannot defy the laws ultimately of gravity or of time or of decomposition.

• 8:05Speaker 02

  I used to be big into New Atheism, right? And that was a movement that was afflicted hugely by a sense within it that people were just smarter than Christians. I see that tendency everywhere now, and I'm sure I'm prone to it as much as anybody. So many social movements now were defined by a feeling of sort of, about the kind of the people, the outside people, that, you know, they're the kind of benighted heathens outside the golden circle.

• 8:27Ryan Holiday?

  Well, you said somewhere, and I think you're right, you said that the story of genius is really the story of ego, or that every genius story is the story of ego. I think the tension of being smart or being right, it can be a real problem. Someone told me once that making a successful contrarian bet can be a sort of cognitively devastating experience because you did a thing and everyone told you you were wrong. Everyone told you you're an idiot. They were incredibly condescending along the way and smug about it, and then you proved them wrong. It is very hard for you to go back to zero on the next thing and the next thing, right?

• 9:12Ryan Holiday?

  You're starting now with a cynicism and a skepticism and a sense of superiority. That is an imbalance that affects your future endeavors and political and social opinions.

• 9:26Speaker 02

  Oh, I completely think that's true. I remember having this conversation with a journalist. There's a British journalist who died a couple of years ago called Christopher Booker. And he became, in his later years, a climate change denialist. And I asked someone who'd worked with him, you know, how did that happen? He was so smart. Like, how did he end up just spending the last 10 years of his life talking about the hockey stick graph and all this stuff we used to hear about before? You know, every summer scorched Texas and wildfires raged across the Midwest. And people kind of went, no, I do think this is a bit weird now. And this other journalist said, well, he was one of the, Christopher Booker was one of the original journalists involved in uncovering the Thalidomide scandal, which was a huge medical scandal in the 1960s in Britain where women were given a morning sickness drug, and it led to limb deformities in their children.

• 10:09Speaker 02

  And for a long time, the medical establishment denied this, covered it up. And it took a really big investigation by The Sunday Times and others to like to bust this open and get people compensation. And he said, essentially, that generation of journalists was ruined by it. Because they had seen this massive conspiracy where the establishment were lying to them. And they were, they were right. And I think that's true. My friend Sarah Diten once said this about the Iraq war ruining the left, right? Being everybody in the left who was like, the Iraq war was a very bad idea. I think this is a foreign policy disaster, you know? And then it was got the idea that actually like this is true of everything. And you just, you know, you end up applying the same paradigm because it was right last time. And as you say, the key thing is that humiliation,

• 10:49Speaker 02

  the humiliation and vindication. And I write about this in the book because I, there's an idea of the kind of scientist as rebel that comes through. You see it in the Galileo story. You see it in Ignace Semmelweis and his work on antiseptics and maternal mortality. That's such a compelling story to us, the idea of the one, usually the one man standing up against the crowd and being laughed at and then being vindicated. It's so unbelievably emotionally satisfying that unfortunately we vastly overindex on it and we see it. You know, we almost want it to happen every time. Cause it's just, whereas obviously that would be absurd. You'd never be able to get in an airplane if it turned out that every, you know, every, every engineering thing was wrong. You'd never go to a hospital if every bit of medicine was actually wrong.

• 11:29Ryan Holiday?

  And when you watch people not engage in good faith with your ideas and be intellectually dishonest. And you watch what you actually really were thoughtful about be sort of caricatured and treated as a straw man. It's hard for you later, when you actually aren't on his sound of footing, not to convince yourself the same thing is happening. And so I, I think you, you see that a lot. And this is actually, I think, the trap of, of scientific genius. It's the trap of entrepreneurial genius. Like everything that worked, it was doubted at the time. I mean, Nikki, our mutual editor, when I came to them and I said, I wanted to write a book about an obscure school of ancient philosophy.

• 12:14Ryan Holiday?

  You know, she told me later that they were like, basically just humoring me and, and that they hoped I would go back to writing marketing books after, right? And so I, I feel like I've had to do a lot of work with the success of that, of reminding myself that it actually was a bad idea. Like the conventional wisdom, like she was not like being elitist. The amount of money that they offered me and the, the expectations they had for the book were, were within the bounds of reason. And made sense, given their past experience. They were not snubbing me. They were not insulting me.

• 12:53Ryan Holiday?

  I did not know better. I had a hunch and they had a hunch and my hunch turned out to be not even right, right? Because it succeeded more than I thought it would succeed. I can't retroactively give myself more prescience than I had because I didn't have any. I was just interested in something and I thought it could work. And the fact that it did work at a pretty extraordinary level, that is a surprise to both parties, right? And so what can happen, I saw this when I was at American Apparel, you know, the idea was insane. What Duff Charney was trying to do and what he was trying to pull off in his, everyone was right to say that it wasn't going to work.

• 13:34Ryan Holiday?

  It worked despite itself. But if you tell yourself a story afterwards that you're a genius and that you knew better. And that all these people are idiots, then you're going to get yourself in trouble later on when you have the other idea. Or when those people go, okay, hey, you did succeed, but you should be careful of X, Y and Z.

• 13:58Speaker 02

  Yeah. They call it Nobel syndrome, I think, don't they? When people win a Nobel prize and then they start going, well, you know, never mind organic chemistry. Wouldn't you like to hear a few of my thoughts about astrobiology?

• 14:10Ryan Holiday?

  Yeah. Didn't Newton get into alchemy?

• 14:12Speaker 02

  Yeah. Newton spent a lot of his life on alchemy and also a lot of his life on something called biblical chronology, which is so wacky that we don't even remember it today. Basically trying to work out when, like when events in the Bible would have happened to work out how old the earth would be from that point. There's loads of examples like that. You know, Marie Curie, one of the greatest scientists, she was, she would go to seances, you know? She would go and see mediums. It was a very popular thing to do at the end of the 19th century. And I think there's an interesting bit about that, right? Because she was working with radiation, which was an invisible force.

• 14:41Ryan Holiday?

  Yes.

• 14:42Speaker 02

  That, you know, that, that was real. So, you know, why not ectoplasm? And I think that's the thing. If you're working at the edge of the kind of the known, then maybe you're, you're sensing you are going to end up with a kind of fluid sense of, of reality. But I think isn't what you're talking about a bit narcissism? If you go along with the conventional wisdom and you're right, that doesn't distinguish you or say anything about you. But if you buck the conventional wisdom and you're right, that means you are better. And I just, I think so much of the troubles we see across our society are essentially narcissism. Conspiracy theorizing fundamentally, to some extent is narcissism, right? It's like your sheeple, your NPCs, and I've seen the truth. I think it's very important to lots and lots of people now to feel special, to not feel ordinary.

• 15:24Speaker 02

  But I think it is a real challenge of, of modern life is working out which experts to trust and which authority to trust and to calibrate that, right? Not to just take everything that you're told by people with letters after their name as gospel, but also not to go so far out that you just, you know, you just don't believe anything at that point.

• 15:47Ryan Holiday?

  I always find it remarkable how easy it is to see ego in other people.

• 15:51Speaker 03

  Oh God.

• 15:53Ryan Holiday?

  As if, and then how insidious it is to see it in yourself.

• 15:56Speaker 03

  Oh, yes.

• 15:57Ryan Holiday?

  You know?

• 15:57Speaker 03

  Horrifying.

• 15:58Ryan Holiday?

  Exactly.

• 15:59Speaker 03

  It's something constantly work on keeping in check, constantly, you know, especially being in a band.

• 16:06Ryan Holiday?

  Yeah. I would say being a lead singer is probably the, of a successful band, maybe even, maybe it's actually harder to be in a not successful band. But there's something about it that is uniquely toxic to the ego.

• 16:19Speaker 03

  Yeah.

• 16:19Ryan Holiday?

  It's like gasoline.

• 16:20Speaker 03

  It's, it, it also is a requirement a little bit, I think, to be the front man of a, of a band is to have a bit of ego or.

• 16:30Ryan Holiday?

  Cause you think I should be the one, I should be the main one.

• 16:32Speaker 03

  Yes. I don't know. It's interesting. I kind of became the singer of my band by mistake.

• 16:37Ryan Holiday?

  Yeah.

• 16:38Speaker 03

  You know, but like to be a good front man, you have to have the willingness to get up and make an idiot out of yourself again. And besides a smidgen of talent, the only requirement to be a good front man is the willingness to get in front of other people and make an idiot of yourself again, again, and again, until you get good at it, right? And in order to do that, I believe there has to be a healthy amount of ego.

• 17:05Ryan Holiday?

  Well, that's why I meant, I think it might actually be worse for the ego to be in a failed or an up and coming band than a successful band. Because a successful band, you can be like, you understand it's unhealthy and you can create some artificial distance.

• 17:18Speaker 03

  Sure.

• 17:18Ryan Holiday?

  Right? And you can be like, it's not about me, you know, I don't want to take it too seriously. You can sort of self-efface. To me, where the ego is required in this sort of performative, whether it's sitting down to write a book and write a song, whatever, is the part of you that goes, everyone wants to hear this.

• 17:35Speaker 03

  Yes.

• 17:36Ryan Holiday?

  When no one has asked for it.

• 17:38Speaker 03

  Right.

• 17:38Ryan Holiday?

  Literally no one has asked for it. And in fact, they're actually telling you for a good chunk of the time you're doing it, that they are fundamentally not interested.

• 17:45Speaker 03

  Yeah.

• 17:46Ryan Holiday?

  Like you are getting rejected over and over and over again.

• 17:49Speaker 03

  Sure.

• 17:49Ryan Holiday?

  And you're like, no, but this is really good. Everyone needs to hear it. And that is the definition of ego, right? Like the rejection of the evidence.

• 17:58Speaker 03

  Right.

• 17:59Ryan Holiday?

  Over your belief or faith in yourself. And so I think in that way, ego can be adaptive early on. The problem is it's so fundamentally maladaptive later on. And this is, I think the, the lead singers or artists or whatever that we know about, that we would say is egotistical, are the ones who are fundamentally stuck at how they were.

• 18:21Speaker 03

  Yes.

• 18:21Ryan Holiday?

  Whatever they had to be to be the up and coming lead singer of Guns N' Roses, you are still the lead singer of, you know?

• 18:28Speaker 03

  Yeah. Yeah. For sure. And we call it LSD, lead singer's disease, you know? He's got a bad case of the LSD. I've managed to keep mine in check.

• 18:44Ryan Holiday?

  I think if you're not looking very closely or you're not very informed.

• 18:48Speaker 03

  Yeah.

• 18:48Ryan Holiday?

  Like you're not savvy, ego and competence look very similar.

• 18:51Speaker 03

  Right.

• 18:52Ryan Holiday?

  Just like mania can look like charisma.

• 18:56Speaker 03

  Yeah.

• 18:56Ryan Holiday?

  But if you, so if you've never been around someone to be like, oh, this is what a crazy person does.

• 19:01Speaker 03

  Yeah.

• 19:01Ryan Holiday?

  You're like, I. Pumped around this guy. You don't realize like it's gonna crash at some point.

• 19:06Speaker 04

  Yeah.

• 19:07Ryan Holiday?

  Especially if you're not confident, the confidence of egotistical or narcissistic. I mean, like you look at the first couple of people that I worked for. I was clearly searching for something. Most people see that kind of boss and run the other way. We're like, I love it here. This is normal.

• 19:25Speaker 04

  Yeah.

• 19:26Ryan Holiday?

  On a long enough timeline, it becomes a disadvantage. That's why I think you can confidently go like ego's the enemy. But it clearly, I mean, there's obviously an extraordinary amount of very successful, very egotistical people.

• 19:39Speaker 04

  Yeah.

• 19:40Ryan Holiday?

  I just think it's, it's two things. One, like you gotta like, that's the myth of, was it Croesus? Where it's like, you can't, you gotta wait till the end till you judge a person happy. But I also think unless you're really, really studying them closely, you're not seeing all the ways that they actually could have been more successful.

• 19:59Speaker 04

  Right.

• 19:59Ryan Holiday?

  So it's like, maybe, yeah, that person's ego makes them shameless enough to ask for stuff that they have no business doing. But by the same token, they tend not to do the work to then earn the thing because they think they're entitled. Like, you know what I mean? Like, it seems like confidence to be like, give me the shot, game's on the line.

• 20:16Speaker 04

  Yeah.

• 20:16Ryan Holiday?

  But like actually a great athlete is like, they know they have to do the work to earn that, you know?

• 20:22Speaker 04

  Yeah.

• 20:23Ryan Holiday?

  And if you're just like, no, no, give it to me, but you don't have the goods. Then you're gonna lose said game when it's on the line.

• 20:28Speaker 04

  Yeah, it's the, the confidence to, to, to want to get the opportunity to, to, to put yourself in that position. Even when I was starting out, it was like, you know, there's these things called bringer shows for standup. Have you heard of that? Like basically you get stage time if you bring five friends. If you bring the audience, you get stage time. And so early on, I like did like an open mic and I like, and then there's a bringer show. They're like, yeah, we can give you stage at the, we can give you stage time at the Comedy Store. I'm like, amazing.

• 20:58Ryan Holiday?

  Yeah.

• 20:58Speaker 04

  And yeah, just bring five friends. So immediately I was like, I'm already on stage at the Comedy Store. This is crazy. And then I quickly, you know, wore out all my friends. I'm like, they were like, dude, we're not coming to any more shows. It was this thing where I had like the naivete or to be like, no, I can be on stage at the Comedy Store. But then quickly learning of like, oh no, it takes, what, what it really takes is two to three open mics a night.

• 21:22Ryan Holiday?

  Yeah.

• 21:22Speaker 04

  Every night for 10 years.

• 21:25Ryan Holiday?

  You need a certain amount of shamelessness to get up and do the thing when you're bad, which you invariably are at the beginning.

• 21:32Speaker 04

  Yeah.

• 21:32Ryan Holiday?

  But you also need like the humility and maybe even the self-loathing.

• 21:37Speaker 04

  Yeah.

• 21:37Ryan Holiday?

  To like, think that you're bad.

• 21:39Speaker 04

  Yes.

• 21:39Ryan Holiday?

  So you do the work to get good.

• 21:41Speaker 04

  Yeah. And you see that a lot. Like the people who will get off stage and being, man, I crushed. And you're like, no, you didn't.

• 21:48Ryan Holiday?

  Yeah. If you walk off feeling like you crushed, it's like the best in the world don't feel that way.

• 21:52Speaker 04

  No.

• 21:52Ryan Holiday?

  So that you feel that way, that, so that's where ego's the enemy because it's, it's making you stay as you are. It's probably more pleasant to not feel shitty.

• 22:03Speaker 04

  Yeah.

• 22:03Ryan Holiday?

  But the shitty is like, Ira Glass talks about this. He's like, there's a taste talent gap.

• 22:08Speaker 04

  Yeah.

• 22:09Ryan Holiday?

  When you start and you have good taste, which is you know what is funny, or you know what's beautiful, or you know what's good writing. But like you can't do it. But the desire to bridge that gap is like the propulsive force that makes you good. But if you're just like, maybe you have good taste, but then you're also biased when it comes to yourself. Or you're delusional when it comes to yourself, that's a problem because now you're just not, you're just like confidently being shitty. If you don't believe you can do something, you're not gonna be able to do it. But just because you believe you can do something is not even close to sufficient to being able to do it.

• 22:42Speaker 04

  Yeah, it's always having this kind of a, this mindset of like, no, there's always room for improvement.

• 22:46Ryan Holiday?

  Yeah.

• 22:47Speaker 04

  Like you're, you're never perfect. Always a student. That's one of my favorite things is just because like, you know, you'll see like Bill Burr. Get off stage at the Comedy Store and he, to me, I'm like, he just crushed.

• 22:57Ryan Holiday?

  Yeah.

• 22:57Speaker 04

  But to him, he's like, oh, that one bit, like I, I'm not getting it right. You know, he's, there's that, there's that criticism. There's like self-criticism of like, no, I need to improve this to really kinda, it's always perfecting it. And it's, it's, it's kinda never reaching that destination, I think.

• 23:13Ryan Holiday?

  Well, Dr. Drew did a study many years ago of he, as guests would come in to Love Line, he gave them like this narcissistic personality test. Cause like, it's interesting, like you, you'd think you'd be able to study narcissism, but most really successful narcissists are obviously inaccessible to like clinical research, right? Most, most studies are done on like college students for class credit, you know?

• 23:36Speaker 04

  Yeah, yeah, yeah.

• 23:37Ryan Holiday?

  So he was able to give this narcissistic personality test to like all the guests. So like a range of celebrities and musicians and then also like reality TV stars and whatever. And what I remember from the study is that they found that, yeah, like most celebrities are, have some level of narcissism. But it's this interesting question of like, are narcissists attracted to celebrity? Or does celebrity make you narcissistic? It's probably a little of both. But one of the things they found was that the more technical the thing you did was, the less narcissistic you were. So like drummers might be very famous because they're in a huge band, but what they do is really fucking hard.

• 24:19Speaker 04

  Yeah.

• 24:19Ryan Holiday?

  And it's like a craft that you love. So it's like inherently humbling and it's inherently about like solving this like puzzle, you know? Versus like someone who was on the Real World Road Rules Challenge is like attractive, in good shape, made a good like pitch video.

• 24:38Speaker 04

  Yeah.

• 24:38Ryan Holiday?

  And then is maybe like dramatic. So like they, they're both famous, but one is getting their ass kicked by the craft of the thing.

• 24:51Speaker 04

  Yeah.

• 24:51Ryan Holiday?

  And the other one is mostly just thinking about like, how can I get more on TV?

• 24:55Speaker 04

  Yeah, it's like the craft itself humbles you and keeps you in check.

• 24:59Ryan Holiday?

  Yeah.

• 25:00Speaker 04

  That makes a lot of sense.

• 25:01Ryan Holiday?

  Standup is like a thing you're going and doing every night. And it's whether you're doing it for a thousand people or 10 people, it's fucking hard.

• 25:08Speaker 04

  And you get humbled by the audience too. If you're not improving, if you're not constantly putting your A game forward, the, the audience will humble you.

• 25:15Ryan Holiday?

  I feel lucky because like my first book came out and did well, but the Stoic stuff was much more gradual. And then I know people who like their first book had just like crushed.

• 25:25Speaker 04

  Yeah.

• 25:25Ryan Holiday?

  That's like, now you're, now you're the person instead of like trying to be the person. I, I spend a lot more time writing than being the writer. If you, if your first thing just, now you're the, you're the guy.

• 25:37Speaker 04

  Yeah.

• 25:38Ryan Holiday?

  The person who did the thing. And that I think can be destabilizing and disorienting.

• 25:47Ryan Holiday?

  The part of you that can't waste a single snap. I mean, I get it because I'm like, the idea of like, I don't actually need this. I can say no to this and be fine. Or like people will be like, hey, do you want to write this thing for this thing? And I'm like, why am I even considering this? Do you know what? Like I have, I have three books I have to write. And then an unsolicited request to do something, now because it's there, I'm considering it, right? And so you can see how the, the, the part of you that goes, no, I, I fucking seize every opportunity that's in front of me. That's what actually makes you a great quarterback, but then it makes it hard for you to be a good quarterback and then regular person.

• 26:28Ryan Holiday?

  Cause you're just that all the time. You're applying the quarterback mentality to, do you want to do this other thing or not? And this other thing is superfluous.

• 26:36Speaker 05

  Yeah. I mean, that entire, in my own way, I can relate to that, what you were saying and like, it's that entire thing. It's that jockeying between insecurity and needing to be praised or the rush you get from a byline. The rush you get from standing in front of people and giving, you know, a speech and having people give you a standing ovation. It's all of those things wrapped up in that. And, you know, when you're out of the quarterback space, there are things in place maybe to check you here or there. Even though it's ultimately up to you. And when you're in that tunnel of the quarterback space, there's very, very few.

• 27:11Ryan Holiday?

  Yeah.

• 27:12Speaker 05

  And that's where I think it becomes difficult. And that's where I think that for all these guys, you know, Steve Young loved Roger Staubach. And he asked Roger Staubach when he retired, because Staubach obviously has probably become the most successful, great quarterback ever in retirement. I mean, he's a real estate, has a real estate empire. And, you know, Steve asked him, like, you seem like you've done pretty good. Like, how do you walk away from football? And Staubach was like, run. You have to run away from the game. You can never look back.

• 27:38Ryan Holiday?

  Interesting.

• 27:39Speaker 05

  And Steve kinda ran, you know, he, he stayed, he kept one, one foot in the pool, but like it's that exact thing. Because Joe Montana, you know, says, I wish that everyone could experience being an NFL quarterback for just one Sunday.

• 27:54Ryan Holiday?

  Yeah.

• 27:54Speaker 05

  Cause then they'd get it.

• 27:55Ryan Holiday?

  Yeah, yeah. Right. But it is, yeah, it's weird. It's like, why was Kobe Bryant like producing movies? Or like, why did Kobe Bryant need a venture capital fund? Some part of it's probably like, yeah, you gotta put that energy somewhere. But also like, if you don't wrestle with why you have that energy, there's just never enoughness. And so you're just doing, doing, and, and, you know, at the end of the day, we all fucking die and nothing happens, you know, like.

• 28:22Speaker 05

  I think that he, and Brady did this too, but I think that he knew that it was gonna be devastating.

• 28:28Ryan Holiday?

  Yeah.

• 28:28Speaker 05

  It was gonna be a death of sorts when he walked away. And so he was looking for exit ramps to, so that when he was exiting, he was exiting into things.

• 28:36Ryan Holiday?

  Yeah.

• 28:37Speaker 05

  And, you know, when you had Brady, here at Brady, you know, has this like career that spans two decades, accomplishes everything you could accomplish. Years before he retired, he had set up his Fox deal. He had these other businesses, you know, he had a production outfit. He had his TB12 quote unquote lifestyle brand, you know, he had all these things he was planning to do. And yet still, he's talked about it where, you know, he'd said he felt like he was like, you know, in a washing machine where you're just bouncing everywhere.

• 29:03Ryan Holiday?

  Yeah.

• 29:04Speaker 05

  And even it got Brady. Even with all of that, it got Brady. And Elway was talking about how, you know, you, you exit, Super Bowl champion, all these things, perfect ending. Then you go into these other spaces and you're behind everyone else.

• 29:19Ryan Holiday?

  Yeah.

• 29:19Speaker 05

  And your name only gets you so far.

• 29:21Ryan Holiday?

  Yeah.

• 29:22Speaker 05

  Elway went and became the GM of the Arena League Colorado Crush. Like what is the great John Elway doing, becoming the GM of an Arena League team and doing these goofy commercials with Jon Bon Jovi?

• 29:34Ryan Holiday?

  Yeah.

• 29:34Speaker 05

  It's because that was his graduate school. He knew that he wanted to get back into football and he wanted to learn how to run a team. And he looked at that like his graduate school for it.

• 29:43Ryan Holiday?

  Yeah, it's funny. You'll be like, why is the president, why is the ex-president on The View? Or what, you know, like, you're like, but like, cause you need your, not your fix, but you're just, you're used to being able to tell people what you're thinking. And like, you know, and then all of a sudden you're just a guy, you know? Like they asked Truman what he did the first day he was out of the White House. And he goes, I, I had to take the suitcases up to the attic. And you're just like, what a come, like that, that's not, there, there's no transition there. And you go from being a not regular to a regular person and you spent your whole life trying not to be regular, right?

• 30:25Ryan Holiday?

  And then, and then it catches up with you and that, that's a, that's a brutal thing. Because if you, if you were content to be a regular person, you would have walked away the second you got like the fuck you wanted.

• 30:38Speaker 05

  Absolutely. You know, Springsteen talks about how he, you know, goes off a cliff into depression when he comes back from a tour. And you go from being king to being a highly paid chauffeur, you know, basically. And, you know, even in his sixties and into his seventies, when he spent his entire life doing this and he knows the ebbs and flows of it, it would still get him. Like that's how powerful that is.