6 Stoic Rules To Beat Ego

Summary

Podcast Summary: "6 Stoic Rules To Beat Ego"

The Daily Stoic Podcast | Host: Ryan Holiday
Date: July 19, 2026

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Episode Overview

This episode of The Daily Stoic delves into the destructive power of ego and offers timeless Stoic principles to keep it in check—what Ryan Holiday calls "rules to beat ego." Through conversation, anecdotes, and ancient wisdom, Holiday and a slate of guests—including a female fighter pilot, a British journalist, a comedian, and a former NFL quarterback—explore how ego manifests, why it can be both a motivator and a downfall, and the practices that help cultivate humility, self-awareness, and effective self-improvement.

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Key Discussion Points & Insights

The Subtleties of Ego

• Ego and Success:
  Ryan opens the episode emphasizing that ego is not essential for success and references historic figures undone by ego (Caligula, Nero, Mussolini). He notes the Stoic antidote: "humility, self-awareness, introspection, reflection" ([00:00]).

• Hidden Ego in Humility:
  The fighter pilot shares how trying to seem “humble” in a hyper-competitive squadron was a kind of ego, driven by fear of looking weak or incompetent:

  “I thought I was too humble...but in hindsight, I realized my ego was actually getting in the way because I saw asking questions, asking for help as weakness.” (Female Fighter Pilot, [01:37])

  Ryan reframes imposter syndrome as a more subtle form of ego:

  “There's an ego even in that kind of imposter syndrome...because you don't want to ask for help, you don't get help...It's actually just a similar self-absorption.” ([01:52])

• Gender Nuances and Extra Pressure:
  The sense of being watched and judged is magnified for underrepresented groups:

  “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 1.” (Female Fighter Pilot, [03:05])

Ego’s Double Edge

• Ego as an Early Advantage:
  Ryan and the pilot discuss how ego or fearlessness can help people break into difficult fields, but becomes dangerous if not checked or matured ([03:36]).

  “Ego makes you go out for things you have no business going out for. In the beginning it’s an advantage, but it becomes costly later.” (Ryan Holiday, [03:36])

• The Importance of Debrief and Taking Criticism: The pilot describes the rigorous post-flight debriefing culture as a way to enforce humility and growth:

  “Every little thing you did wrong in the air is picked apart...And no one is spared from being criticized.” (Female Fighter Pilot, [05:17])

  Not being open to constructive criticism is “failure to take instruction,” which can get you kicked out for safety ([06:04]).

The Stoic View on Mortality and Legacy

• Hadrian’s Mausoleum:
  Ryan uses the story of Hadrian’s massive tomb to emphasize Marcus Aurelius’s reminder of our mortality and the futility of ego:

  “Marcus Aurelius would have found this to be the antithesis of Stoic philosophy...You are not immortal. You are not a God. You cannot defy the laws ultimately of gravity or of time or of decomposition.” (Ryan Holiday, [06:12])

  Even mighty emperors are forgotten in the end, as Marcus observed:

  “Alexander the Great and his mule driver, they both died. And the same thing happened to both.” (Ryan Holiday, [06:12])

Ego in Social Movements, Genius, and Vindication

• Ego in Social Movements:
  The British journalist reflects on how movements can become defined by a contempt for outsiders:

  “So many social movements now were defined by a feeling of the kind of the people, the outside people...they're the kind of benighted heathens.” (British Journalist, [10:13])

• The Trap of Vindicated Genius:
  Ryan and the journalist discuss the danger when people who were right against the crowd once, then become convinced they’re always right—what leads to “Nobel syndrome”:

  “It's very hard for you to go back to zero on the next thing...you're starting now with a cynicism and a sense of superiority.” (Ryan Holiday, [10:35])

  The journalist relays how such vindication leads to cognitive traps:

  “The humiliation and vindication...the idea of the scientist as a rebel. It's so emotionally satisfying we vastly over-index on it.” (British Journalist, [11:33])

• Retrospective Self-Deception:
  Ryan admits to his own temptation to inflate his prescience after success:

  “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.” (Ryan Holiday, [13:37])

Confidence vs. Ego in Creative and Athletic Domains

• Performer’s Ego:
  Being on stage or in the spotlight requires some ego but can easily turn toxic if unchecked.

  "To be a good frontman, you have to have the willingness to get up and make an idiot of yourself again and again." (Comedian, [18:48]) "The definition of ego: the rejection of the evidence over your belief or faith in yourself." (Ryan Holiday, [19:46])

• Adaptive Early, Maladaptive Later:

  "Ego can be adaptive early on. The problem is it’s fundamentally maladaptive later on." (Ryan Holiday, [20:29])

• Humility is Essential for Growth:
  The difference between confidence and ego comes down to attitude toward work and improvement:

  "You need a certain amount of shamelessness to get up and do the thing when you're bad...But you also need the humility...to think that you're bad, so you do the work to get good." (Ryan Holiday, [23:33])

  Reliable self-criticism marks mastery:

  "The best in the world don’t feel like they crushed it every night." (Ryan Holiday, [23:56]) "That’s where ego is the enemy, because it’s making you stay as you are." (Ryan Holiday, [24:00])

• The Humbling Power of Craft:
  Tasks that require technical skill (e.g., musicianship, comedy, writing) inherently knock down narcissism:

  "The more technical the thing you did, the less narcissistic you were. The craft itself humbles you and keeps you in check." (Ryan Holiday, [25:45], [27:03])

The Endgame: Ego After Achievement

• Struggle with Ordinary Life After Success:
  Retired athletes, politicians, and artists often flounder in the absence of the intense feedback and identity previously available to them:

  "Your name only gets you so far...you go from being a not regular to a regular person, and you spent your whole life trying not to be regular." (Ryan Holiday, [31:27], [32:32])

  Springsteen's post-tour depressions and Tom Brady’s “washing machine” analogy for retirement are cited as examples ([32:47]).

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6 Stoic Rules To Beat Ego (Implicit in the Episode)

1. Recognize Ego’s Many Forms:
   – From grandiosity to insecurity to self-absorption—ego manifests differently and often hides behind false humility.

2. Seek Humility through Self-Examination:
   – Regular reflection, rigorous debrief, and willingness to ask for help keep ego in check ([05:17]).

3. Own Mistakes and Critique:
   – Constructive criticism and honest self-assessment are prerequisites for real improvement; avoid making excuses ([06:01]).

4. Remain a Student:
   – “You’re never perfect, always a student” ([24:55]). The best keep learning, never growing too enamored of their own hype.

5. Embrace Mortality and Perspective:
   – Remember that status, praise, even legacy is fleeting. “You are not immortal...You cannot defy the laws of time or decomposition.” ([06:12])

6. Detach Identity from Achievements:
   – Don’t let roles—be it athlete, performer, leader—define the self. Prepare for transitions and practice detachment ([32:32]).

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Notable Quotes & Memorable Moments

• “Because you don’t want to look stupid, you’ll stay stupid. Because you don’t want to ask for help, you don’t get help.”
  — Ryan Holiday ([01:52])

• “The irony is it gets you what you want, and now the stakes are much higher...pride goeth before the fall.”
  — Ryan Holiday ([04:02])

• “Every genius story is the story of ego.”
  — Ryan Holiday paraphrasing the journalist ([10:35])

• “The craft itself humbles you and keeps you in check.”
  — Ryan Holiday ([27:03])

• “You need a certain amount of shamelessness to get up and do the thing when you're bad...but you also need the humility to think that you’re bad, so you do the work to get good.”
  — Ryan Holiday ([23:33])

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Timestamps for Key Segments

• [00:00] Introduction: The dangers of ego and why Stoics advocate humility
• [01:03–03:36] Fighter pilot on ego, humility, imposter syndrome, and gender in high-pressure careers
• [05:17–06:12] The value of critique and reflection; consequences of unteachable ego
• [06:12–09:15] Story of Hadrian’s mausoleum: mortality, futility of ego
• [10:13–13:37] Ego in social movements, vindicated genius, “Nobel syndrome”; pitfalls after being “proved right”
• [18:30–24:00] Ego vs. confidence in performing arts, the necessity of humility for improvement
• [24:55–27:03] Technical skill, the humbling power of craft, Dr. Drew’s narcissism study
• [29:20–33:09] Transition out of success: athlete/leader experiences, struggle with ordinary life

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Conclusion

This episode untangles the complex role of ego in our ambitions and achievements—showing both its drivers and its pitfalls. Drawing on Stoic wisdom, personal anecdotes, and candid reflections from high achievers across domains, Ryan Holiday and guests make a powerful case for humility, continual self-scrutiny, and the ongoing fight against the insidious pull of ego. For Holiday and his guests, mastery over the self—and the ego—remains a daily practice, never a finished achievement.

Transcript

[Ryan 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. 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. Who were Caligula, Nero, Xerxes, Mussolini, and then, of course, business and art, 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.

[Female Fighter Pilot]

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. Like, you're really establishing your reputation in this career field you're going to be in for a decade.

[Ryan Holiday]

Yeah.

[Female Fighter Pilot]

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.

[Ryan Holiday]

Yeah.

[Female Fighter Pilot]

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.

[Ryan Holiday]

Yeah.

[Female Fighter Pilot]

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

[Ryan 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. 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. 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. But it's actually just a similar self absorption.

[Female Fighter Pilot]

Yeah. My whole world revolved around me and 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.

[Ryan Holiday]

Yeah.

[Female Fighter Pilot]

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

[Ryan Holiday]

Yeah.

[Female Fighter Pilot]

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 1.

[Ryan Holiday]

You're just spending too much time thinking about what other people are thinking and you don't realize. But 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 schematics or whatever.

[Female Fighter Pilot]

It's a massive distraction.

[Ryan 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.

[Female Fighter Pilot]

I feel like not being afraid of things you should be afraid of.

[Ryan Holiday]

Right.

[Female Fighter Pilot]

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

[Ryan 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, you think you're exempt or you've made a bunch of enemies or again, yeah, you've picked up really bad habits or, 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, 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. And that's why they say pride goeth before the fall. At what level do you want that fall to happen?

[Female Fighter Pilot]

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.

[British Journalist/Commentator]

Yeah.

[Female Fighter Pilot]

That can get you places initially.

[Ryan Holiday]

Yeah.

[Female Fighter Pilot]

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. 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.

[Ryan Holiday]

Yeah.

[Female Fighter Pilot]

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.

[Ryan Holiday]

Yeah.

[Female Fighter Pilot]

It's just failure to take instruction.

[Ryan Holiday]

Yeah.

[Female Fighter Pilot]

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 because it's dangerous.

[Ryan Holiday]

Yeah. 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. Now, you might think the fact that this is still here 2,000 years later, that. That it's. 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 Rios 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 happen to Augustus, or 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. 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. Hey, it's Ryan. I'm on the road right now, doing talks all over the country. I love traveling. I love going to new places. The thing I don't like about it, though, is I don't get to sleep in my bed at home, which I like, not just because it's home, but because I have an eight sleep on my bed. I've had an eight sleep on my bed. I don't know, five years. I love it. My wife loves it. We love it because it cools the mattress. It heats the mattress. You can have different sides, cool the different temperatures. It's even how I wake up in the morning. Instead of an annoying alarm clock or that, you know, horrible sound on your phone, it lightly buzzes you awake, and then. And then when you're up, you want to turn it off, you just tap the mattress. There's all sorts of awesome features in my eight Sleep. It was worth every penny. The point is, I love my Eight Sleep. And the Eight Sleep keeps getting better. Eight Sleep users report up to 32% better sleep and up to 34% better deep sleep. This is all stuff you love. You can use the code [e-mail] Dailystoic do now for up to $500 off. And this Fourth of July sale ends on July 12th, so don't wait. And if you have an HSA or an FSA. Some eight sleep stuff qualifies for that as well through True Med and qualified customers save about 30% on average. Check your eligibility@True Med.com 8. Sleep before you buy True Med is for qualified customers. HSA and FSA tax savings may vary. Back to school starts now. Get long lasting battery life on the Dell XPS Lapt powered by Series 3 Intel Core, so you can work from anywhere. And now starting at $699 with exclusive student pricing starting at $599. It's lightweight, portable and packed with enough processing power to make multitasking a breeze. So say goodbye to distractions and hello to more free time because you finished your work faster. Complete your setup with savings on select monitors and more. Must have electronics and accessories, limited time deals and free shipping on PCs and more await [e-mail] that's Dell.com deals.

[British Journalist/Commentator]

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.

[Ryan 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? 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.

[British Journalist/Commentator]

Oh, I completely think that's true. I remember having this conversation with a journalist, as 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. 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 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 right. And I think that's true. My friend Sarah Dighton once said this about the Iraq war ruining the left, right, being everybody in the left who was like, the Iraq war is a very bad idea. I think it's 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, the humiliation and vindication. And I write about this in the book because 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 Ignaz 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 over index on it. And we see it, you know, we almost want it to happen every time because it's just. Whereas obviously that would be absurd. You'd never be able to get in an airplane if it turned out that, you know, every, every engineering thing was wrong. You never go to a hospital where every bit of medicine was actually wrong.

[Ryan 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 as sound a footing, not to convince yourself the same thing is happening. And so I Think you see that a lot. And this is actually, I think, the trap 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, 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 expectations they had for the book were within the bounds of reason and made sense, given their past experience. They were not snubbing me. They were not insulting me. 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.

[Comedian]

Right.

[Ryan Holiday]

And so what can happen? I saw this when I was at American Apparel. You know, the idea was insane, what Dove Charney was trying to do and what he was trying to pull off. And he's like, everyone was right to say that it wasn't going to work. 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. Yeah.

[British Journalist/Commentator]

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?

[Ryan Holiday]

Yeah. Didn't Newton get into alchemy?

[British Journalist/Commentator]

Yeah, Newton spent a lot of his life in 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.

[Ryan Holiday]

Yes.

[British Journalist/Commentator]

That, you know, but 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 your sense of you are going to end up with quite a fluid sense 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 you're sheeple, you're 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. But I think it is a real challenge 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.

[Ryan Holiday]

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

[Former NFL Quarterback]

Oh, God.

[Ryan Holiday]

As if. And then how insidious it is to see it in yourself. Oh, yes. You know, horrifying. Exactly. It's something constantly work on keeping in check. Constantly. You know, especially being in a band. Yeah. I would say being a lead singer is probably of a successful band. Maybe it's actually harder to be it in a not successful band. But there's something about it that is uniquely toxic to the ego. Yeah. It's like gasoline.

[Comedian]

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

[Ryan Holiday]

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

[British Journalist/Commentator]

Yes.

[Comedian]

I don't know. It's interesting. I kind of became the singer of

[Ryan Holiday]

my band by mistake. Yeah. You know, but like to be a

[Comedian]

good front man, you have to have the willingness to get up and make

[Ryan Holiday]

an idiot out of yourself again.

[Comedian]

And besides a smidgen of talent, the

[Ryan Holiday]

only requirement to be a good frontman

[Comedian]

is the willingness to get in front

[Ryan Holiday]

of other people and make an idiot of yourself again and again and again until you get good at it.

[Comedian]

Right.

[Ryan Holiday]

And in order to do that, I believe there has to be a healthy amount of ego. Well, that's why it 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.

[Former NFL Quarterback]

Sure.

[Ryan Holiday]

Right. You can be like, it's not about me, you know, I don't want to take it too seriously. You can serve self employment face. To me, where the ego is required in the 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.

[Female Fighter Pilot]

Yes.

[Ryan Holiday]

When no one has asked for it.

[Comedian]

Right.

[Ryan 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. Like you are getting rejected over and over and over again and you're like, no, but this is really good and everyone needs to hear it. And that is the definition of ego. Right. Like the rejection of the evidence 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 lead singers or artists or whatever that we know about that we would say as egotistical are the ones who are fundamentally stuck at how they were.

[British Journalist/Commentator]

Yes.

[Ryan 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 Guns, you know. Yeah, yeah.

[Former NFL Quarterback]

For sure.

[Comedian]

And we call it lsd, Lead singer's disease.

[Ryan Holiday]

You know, he's got a bad case. The lsd. I managed to keep mine in check. I think if you're not looking very closely. Yeah. Or you're not very informed.

[Comedian]

Yeah.

[Ryan Holiday]

Like you're not savvy. Ego and confidence look very similar.

[Comedian]

Right.

[Ryan Holiday]

Just like Mania can look like charisma.

[Comedian]

Yeah.

[Ryan Holiday]

But if you. So if you've never been around someone to be like, oh, this is what a crazy person does. Yeah. You're like, I'm pumped around this guy. You don't realize, like, it's going to crash at some point. Yeah. Especially if you're not confident. The confidence of egotistical or narcissistic. I mean, like, you look at the first couple 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. Yeah, this is normal. 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.

[Comedian]

Yeah.

[Ryan Holiday]

I just think it's. It's two things. One, like, you got, like. That's the myth of. Was it Croesus? Where it's like, you can't. You got to wait till the end to 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.

[Comedian]

Right.

[Ryan 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 entirely like, yeah, you know what I mean? Like, it seems like confidence to be like, give me the shot. Game's on the line.

[Comedian]

Yeah.

[Ryan Holiday]

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

[Comedian]

Yeah.

[Ryan Holiday]

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

[Comedian]

Yes. It's the confidence to want to get the opportunity 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 stand up. Have you heard of that? Basically, you get stage time if you bring five friends. If you bring the audience, you get stage time. And so early on, I did an open mic, 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. And I'm like, amazing.

[Ryan Holiday]

Yeah.

[Comedian]

And, yeah, just bring five friends. So immediately I was like, I'm already on stage at the Comedy Store.

[Ryan Holiday]

This is crazy.

[Comedian]

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 it really takes is two to three open mics a night.

[Ryan Holiday]

Yeah.

[Comedian]

Every night for 10 years. Yeah.

[Ryan 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.

[Comedian]

Yeah.

[Ryan Holiday]

But you also need, like the humility and maybe even the self loathing to like, think that you're bad.

[Comedian]

Yes.

[Ryan Holiday]

So you do the work to get good. Yeah.

[Comedian]

And you see that a lot. Like the people who will get off stage and be like, man, I crushed.

[Ryan Holiday]

Yeah.

[Comedian]

Like, no, you didn't.

[Ryan Holiday]

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

[Comedian]

No.

[Ryan Holiday]

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

[Comedian]

Yeah.

[Ryan Holiday]

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

[Comedian]

Yeah.

[Ryan 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 your 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.

[Comedian]

Yeah.

[Ryan Holiday]

Just because you believe you can do something is not even close to sufficient to being able to do it.

[Comedian]

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

[Ryan Holiday]

Yeah.

[Comedian]

Like, 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 Berg got the stage at the Comedy Store and he, to me, I'm like, he just crushed.

[British Journalist/Commentator]

Yeah.

[Comedian]

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 kind of. It's always perfecting it and it's, it's, it's kind of never reaching that destination, I think.

[Ryan Holiday]

Well, Dr. Drew did a study many years ago of he. As guests would come in to Loveline, he gave them, like, this narcissistic personality test because, 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.

[Former NFL Quarterback]

Most.

[Ryan Holiday]

Most studies are done on, like, college students for class credit, you know.

[Comedian]

Yeah. Yeah.

[Ryan 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. 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. Yeah. 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. Yeah. And the other one is mostly just thinking about, like, how can I get more on tv?

[Comedian]

Yeah. It's like the craft itself humbles you. Yes. And keeps you in check.

[Ryan Holiday]

Yeah.

[Comedian]

That makes a lot of sense.

[Ryan Holiday]

Stand up 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.

[Comedian]

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

[Ryan 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, it just, like, crushed.

[Comedian]

Yeah.

[Ryan Holiday]

That's, like, now you're. Now you're the person instead of, like, trying to be the person. 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. The person who did the thing that I think can be destabilizing and disorienting, The part of you that can't waste a single snap. I mean, I get it because I'm that way. 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, Like, 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 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, because 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.

[Former NFL Quarterback]

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.

[Ryan Holiday]

Yeah.

[Former NFL Quarterback]

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.

[Ryan Holiday]

Interesting.

[Former NFL Quarterback]

And Steve kind of ran. He stayed. He kept 1.1foot in the pool. But, like, it's the exact thing. Because Joe Montana, you know, says, I wish that everyone could experience being an NFL quarterback for just one Sunday.

[Comedian]

Yeah.

[Former NFL Quarterback]

Because then they'd get it.

[Female Fighter Pilot]

Yeah.

[Ryan Holiday]

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 got to 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 die and nothing happens. You know, like, I think that he

[Former NFL Quarterback]

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

[Ryan Holiday]

Yeah.

[Former NFL Quarterback]

It was going to 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.

[British Journalist/Commentator]

Yeah.

[Former NFL Quarterback]

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 said he felt like he was like, you know, in a washing machine where you're just bouncing everywhere.

[Ryan Holiday]

Yeah.

[Former NFL Quarterback]

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.

[Ryan Holiday]

Yeah.

[Former NFL Quarterback]

And your name only gets you so far.

[Ryan Holiday]

Yeah.

[Former NFL Quarterback]

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.

[Ryan Holiday]

Yeah.

[Former NFL Quarterback]

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 school for it.

[Ryan 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, you're like. But, like, because 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 this 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.

[Comedian]

Right?

[Ryan Holiday]

And 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 went absolutely.

[Former NFL Quarterback]

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 60s and into his 70s 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.

[Comedian]

It.