#321 Ryan Holiday - The Stoic Survival Guide

Summary

The Shawn Ryan Show #321 – Ryan Holiday: The Stoic Survival Guide

Date: July 13, 2026
Host: Shawn Ryan
Guest: Ryan Holiday

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Episode Overview

In this episode, Shawn Ryan sits down with bestselling author and modern Stoic, Ryan Holiday, for an in-depth conversation on the role of Stoicism in surviving and thriving during turbulent times. The discussion ranges from the practical application of Stoic philosophy in daily life, parenting, personal growth, and leadership, to the ethics of media, the dangers of ego, and the quest for authentic masculinity. Both men get deeply personal about the challenges of fatherhood, the temptations of success, and navigating a noisy, divided world with resilience and virtue. The tone is candid, pragmatic, and charged with urgency for meaningful action—true to the show's reputation for “real stories from real people.”

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Key Discussion Points and Insights

1. Stoicism as a Survival Guide in Turbulent Times

• Opening Theme: Shawn shares his aim to become “a little more stoic” for his family amid global chaos.
• Meditations & Marcus Aurelius: Ryan gives Shawn his favorite translation of “Meditations,” celebrating it as, “the private thoughts of the most powerful person in the world, almost certainly not intended for publication...he might be mortified we’re holding this right now.” (01:24)
• Core Insight: Stoicism isn't about bottling emotions but acknowledging them and returning to center. “Fight to be the person that philosophy tried to make you.” (Ryan, 03:02)
• On Parenting: Both reflect on becoming less naturally stoic after having kids: “There are people who are kind of naturally there, and then you have kids and realize you’re not there at all.” (Ryan, 00:47)

Memorable Quote

“You seem stoic, though. Lowercase stoic. Are you not?”
— Ryan Holiday (00:28)

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2. Book Recommendations for Stoic Living and Parental Wisdom (04:04–10:27)

• Ryan recommends several books that have influenced his own thinking and fatherhood: “Inside or Outside Kids in an Inside World” by Steve Rinella, a biography of Churchill and his son, the writings of James Stockdale, and a political profile of Hunter S. Thompson (“Freak Kingdom”).
• On Outdoor Parenting:

  “Kids love it when they’re out there, but they hate the process of getting out there. The struggle is the starting.”
  — Ryan Holiday (05:17)

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3. Practical Stoicism: Dealing with Anxiety, Revenge, and Social Upheaval

Anxiety and Depression (Related to Stoicism)

• Listener Q&A: Ryan addresses how the Stoic principle of separating oneself from one’s thoughts can help those struggling with anxiety and depression:

  “You have the opinion, the anxiety... and you’re trying to take a second and ask yourself: Is this true?...Is worrying about this affecting the outcome in any way, or am I just torturing myself?” (Ryan, 12:05)

• Release Valve—Not Bottling Up: Shawn worries Stoicism might promote emotional suppression. Ryan counters:

  “We take ‘stoic’ to mean, like, you don’t feel anything. That’s not what it is. It’s about processing that emotion, asking if it’s productive.” (16:53)

• Ryan cites Marcus Aurelius frequently crying as proof that emotional expression is compatible with Stoicism.

Revenge & Energy Management

• Shawn describes time wasted on planning revenge:

  “I would waste an entire day planning all the things I could do to somebody that took advantage of me... in retrospect, it’s just a total waste of energy.” (27:55)

• Ryan reframes it:

  “We hand our minds over to people all the time... We let them take up inordinate amounts of time and space in our life... You have to have some mechanism by which you put up boundaries.” (28:18)

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4. Politics, Information Overload, and Historical Perspective

• On Politics and News Media:

  “Corruption’s not new. Hypocrisy is not new. Declining empire is not new. The only thing new is we have more information in real-time.” (Ryan, 22:19)

• Ryan warns against consuming only current news and urges a deep dive into history to gain context and perspective.
• Sensationalism and Incentive Structures in Media:

  “The valence of the extremeness of emotion is the number one predictor of virality... It creates an incentive for extremes.” (Ryan, 50:46)

• “Most people watch too much news and don’t read enough history.” (Ryan, 22:19)
• Both discuss the rise of “clip culture,” audience capture, and the moral responsibilities of people with platforms.

Memorable Quote

“It’s our job as citizens in America to be informed. But watching the news in real-time isn’t necessarily the best way.”
— Ryan Holiday (22:19)

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5. Fatherhood, Self-Awareness, and Hypocrisy

On Being Role Models and Finding Balance

• Self-Reflection: Both admit to struggling to find their own hypocrisy despite being quick to notice it in others (Sean, 80:46). Ryan stresses the importance of having systems (like boards or spouses) that correct one’s course.

  “As you become powerful... When you get a reputation for punishing critics, it degrades your picture of the world.” (81:04)

• Checks and Balances: Ryan draws lessons from ancient Rome to modern politics, advocating for hearing difficult truths from others to maintain humility and effectiveness.

On Setting Examples and Emotional Labor

• Ryan describes the challenge of raising kids with privilege without entitlement, and the importance of modeling humility, resilience, and values through one's own actions.

  “Your kids don’t always listen, but they’re always watching.” (168:12)

• On Apologizing to Kids:

  “There are things that, 30 years later, if my parents apologized for, it would mean a lot to me... How quickly can you do it now?” (171:19)

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6. Confronting Mortality and Living in the Present

• Ryan introduces the memento mori practice, urging reflection on mortality:

  “The time that passes belongs to death... How we spend our time is how we spend our life.”

• Shawn adds,

  “Every time I thought I was gonna die, there's only one thing that goes through your mind: your family. That’s it.” (121:01)

• They discuss the difficulty ingraining these lessons—how "life creeps back in," and the necessity of continually resetting one’s focus (115:22–125:23).

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7. Ego, Ambition, and Humility

• Ego: “I like to think of ego as being the thing that gets between you and whatever it is you want to do.” (97:35)
• “The more successful you are, the more self-critical and aware you need to be. Success enables people to inflate your ego for you.” (Ryan, 98:53)
• Humility and Growth: “Confidence is, to me, an awareness of strength and an awareness of weakness. Knowing what you’re not good at, what you need to get better at—that’s a big part.” (Ryan, 107:51)
• Practical Parenting Insight:

  “Most of the conflict… doesn’t matter. Pick your battles. Avoid 99.9% of them.” (Ryan, 130:21) Regarding influence: “If you were tried in court, would you be convicted of those beliefs from your actions?” (168:12)

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8. Raising Resilient, Grounded Kids Amid Privilege

• Both wrestle with how to raise kids around new wealth without entitlement or materialism.

  “You could spend all your time constructing a will, but not enough raising a person with enough character to handle it.” (Ryan, 163:17)

• On Modeling the Right Relationship with Money:

  “The most valuable gift you can give your kid is not a huge estate. It's the ability to find the thing that lights them up.” (164:17)

• Key is modeling—how you treat stuff, people, problems is what kids absorb regardless of explicit advice.

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9. On Reading, Learning, and Advice for Growth

• Ryan advises against speed-reading for its own sake:

  “You’re not like, how do I eat food faster? Or is there a way to have sex faster? The point is, stuff that’s good, you want it to take how long it’s supposed to take.” (177:45)

• Reading is “magic... books are door-shaped, portals to another world.” (178:17)

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10. Hot Question Segment: Audie Murphy & Real Masculinity

Timestamps: 182:25–190:03

Question:

What does Audie Murphy’s story (the smallest, quietest guy in the room becoming the most decorated soldier in US history) tell us about real toughness?

Notable Response:

• “There’s physical courage, and then there’s moral courage… The moral courage to say, ‘Hey, I’m not going to do that, this doesn’t feel right to me’—we don’t celebrate enough… If the ideas of masculinity and toughness and resilience—if that’s what initially attracts you to stoicism, awesome. But you can’t stop there.” (Ryan, 186:09)
• Explicit rejection of pop “alpha male stoicism” as promoted by influencers like Andrew Tate:

  “Andrew Tate is a fucking abuser of women… Stoicism is not a recipe for making you a better sociopath.”

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Timestamps for Important Segments

| Segment | Timestamp | | --------------------------------------------------| ------------ | | Introduction, the draw to Stoicism | 00:11–03:35 | | Book recommendations, parenting themes | 04:04–10:27 | | Audience Q: Stoicism for anxiety/depression | 11:46–14:59 | | Not bottling emotions, real Stoicism vs stereotype| 16:14–21:04 | | Politics, media, and information literacy | 22:19–55:42 | | Audience capture & platform responsibility | 59:54–64:55 | | Self-reflection, hypocrisy, and historical models | 80:17–95:03 | | Ego and humility—deep dive | 97:29–114:44 | | Death, memento mori, and living for family | 115:22–126:14| | Parenting, examples, and apologizing to kids | 130:19–173:43| | Wealth, privilege & raising good kids | 159:34–168:12| | Speed reading and the magic of books | 177:39–182:16| | Audie Murphy & real masculinity—“hot question” | 182:25–190:03|

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Notable Quotes (with Timestamps)

• “Fight to be the person that philosophy tried to make you.” — Ryan Holiday (03:02)
• “We take ‘stoic’ to mean, like, you don’t feel anything. That’s not what it is. It’s about processing that emotion, asking if it’s productive.” — Ryan Holiday (16:53)
• “Most people watch too much news and don’t read enough history.” — Ryan Holiday (22:19)
• “If you allow the shittiness of what’s happening around you to make you feel shitty and, worse, to be shitty, like, they are winning.” — Ryan Holiday (23:02)
• “Your kids don’t always listen, but they’re always watching.” — Ryan Holiday (168:12)
• “There are things that, 30 years later, if my parents apologized for, it would mean a lot to me.” — Ryan Holiday (171:19)
• “Success enables people around you to inflate your ego for you.” — Ryan Holiday (98:53)
• “Reading is magic. Books are door-shaped; they're portals to another world.” — Ryan Holiday (178:17)
• “There’s physical courage, and then there’s moral courage… The moral courage to say, ‘Hey, I’m not going to do that, this doesn’t feel right to me’—we don’t celebrate enough.” — Ryan Holiday (183:40)
• “Stoicism is not a recipe for making you a better sociopath… If that’s what attracts you, fine. But you can’t stop there.” — Ryan Holiday (186:09)

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Summary Takeaways

• Real Stoicism is not suppression—it’s honest self-examination, returning to center, striving for virtue, and having emotional release valves.
• Fatherhood is a crucible—how you act and what you model (especially humility, resilience, boundaries) matters far more than what you say.
• Success and Ego: The greater the success, the greater the challenge to remain self-aware and open to dissent; ego unchecked is dangerous.
• Media and Truth: Both the news economy and social media incentivize sensationalism and confirmation bias; personal responsibility for truth is paramount.
• Courage and Justice: True toughness requires moral courage—standing up for justice, choosing not just to be strong but to be good.
• Family: In crisis, the only thing that matters is family—so live and schedule accordingly, with humility about the fleetingness of time with them.

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Final Thought

This episode is a masterclass in actionable wisdom for modern survival—at home, in public life, and within. Ryan and Shawn’s brutally honest conversation offers profound guidance on how to weather chaos with grace, raise grounded children, and maintain integrity in a noisy, transactional world. Virtue, not bravado, is the true mark of toughness.

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Transcript

[Sean Ryan]

Foreign. Holiday. Welcome to the show, man.

[Ryan Holiday]

Yeah, thanks for having me.

[Sean Ryan]

It's an honor to have you.

[Ryan Holiday]

Likewise.

[Sean Ryan]

So, yeah, this year, one of my goals is to become a little more stoic as the political and world current events just continue to spiral out of control. That's been one of my goals, primarily for my family. You know, it's just.

[Ryan Holiday]

You seem stoic, though. Lowercase stoic. You seem. Are you not?

[Sean Ryan]

I tend to lose my shit every once in a while, but. As we all do. But, yeah, I just. I want to be a little more stoic, primarily for my family. My kids.

[Ryan Holiday]

Yeah, I'm the same way. I mean, I think there's some people who are sort of naturally there, and then you have kids, and then you realize you're not there at all.

[Sean Ryan]

Yeah, yeah, but. And actually several. My wife's been wanting me to do this for a while, and I'll bet it five, six years ago, she gave me one of your books. And that's when I first heard about you and read it. It was like a daily.

[Ryan Holiday]

Yeah, a daily. Stoic, maybe. Stoic, yeah.

[Sean Ryan]

And read through that. And then this year got Marcus Aurelius's book on stoicism. And. And so this is perfect. Now you're here.

[Ryan Holiday]

All right, well, I brought you a good edition of Marcus Rios. I don't know which one you have. This is my favorite translation. So I think what's cool about this is like, am I out of the way here? You have the private thoughts of the most powerful person in the world and almost certainly not intended for publication. Like, he might be mortified that we're holding this right now. So most books are written for the audience. Right. But this is a book for the author. That it's a book is the byproduct of the philosophical process, which is like, he has a temper, he has anxiety, he has a shitty job with people he can't trust and an empire that's coming apart. And he has health problems, he has marital problems, he has a plague, there's floods. It's a series of endless wars. And what he's doing is sitting down and writing to himself, trying to get back to center.

[Sean Ryan]

Right, interesting.

[Ryan Holiday]

And it just wasn't burned upon his death or it wasn't destroyed when he died. And so it doesn't read like a typical book. I mean, it's 12 books. Each passage is numbered. But it's really almost like journal or diary entries, because that's what stoicism is, is like this. You know, how you're trying to be and then you're here. There's a great line in Meditations where he's saying, like, fight to be the person that philosophy tried to make you, and that's what he's doing in meditation.

[Sean Ryan]

Can you say that again?

[Ryan Holiday]

He says, fight to be the person that philosophy tried to make you, or fight to be the person that philosophy wants you to be. Right. It's like, we all know the idea, the ideal, like, what our best self is. And then we're dysregulated or we're tired, or we're hungry, or somebody's being really awful and annoying. And. And we're. We're struggling to be. To get from the lower self to the higher self.

[Sean Ryan]

Gotcha.

[Ryan Holiday]

Right? And that's what. That's what this is. So I got this. And then this. This one will hopefully, like, Meditations should be.

[Sean Ryan]

Thank you.

[Ryan Holiday]

It should be a book that you like. Most books you read. Right. Meditation should be a book that you are reading. Like, it should sit on the nightstand and you pick it up and you read it throughout your life, because it was written throughout someone's life. But the idea is that you don't know what passage you're going to need until you're flipping through the book and it jumps out at you. That's the idea of meditations.

[Sean Ryan]

Roger that. Thank you.

[Ryan Holiday]

All right, I got a bunch more. I won't take so much time, but I know you got young kids. Do you know Steve Rinella? Yeah, he's a meat eater. This is. I think this is. He wrote an amazing book about hunting called the American Buffalo, which is, like one of my favorite books, where he gets a buffalo tag in Alaska and he goes to hunt the American bison, and it's all about that. That's my favorite Steve Rinella book. But as a parent, this is inside or outside kids in an inside world. I think that's what every parent is struggling with right now. Cause screens are so addictive and video games are so exciting. And we're all glued to our devices. Right. I mean, people are probably listening to this, almost certainly listening to this on a device right now. But the point is, you wanna raise outdoor kids, right? Kids, he says, you wanna raise kids that don't say ew a lot. Cause they're good. Being outside, getting dirty, doing nonsense that. I love that book. I think it's amazing.

[Sean Ryan]

Do you. You spend a lot of time outdoors with your kids?

[Ryan Holiday]

Yeah, we live on a ranch in Texas, so that. So we're. We're. We're pretty outdoorsy. But, you know, it's a constant fight. It's like. It's like they love it when they're out there, but they hate the process of getting out there.

[Sean Ryan]

Really.

[Ryan Holiday]

Do you know what I like? It's like when we were. Yesterday, we went on a hike. They did not want to get out of the car. They did not want to go on it. And then as soon as they. We were in it, they loved it. Right? And that's like. I think the struggle is the starting. You know what I mean?

[Sponsor/Ad Voice]

Yep.

[Ryan Holiday]

All right, so we got that. Oh, this is another interesting parenting one. This is about Churchill and his son. So Churchill has a horrible father and horrible mother. Basically neglect him, becomes a great man, and he tries to do better with his son, but he doesn't do a great job. And I think that's another thing that keeps us up at night as parents is like, if you're successful, how do you not raise spoiled, entitled kids? They have comforts and security and love that maybe we didn't get. But how do you make sure that that works to their advantage, not that they're to their disadvantage? Right? And so I thought it's a really interesting sort of. Because it looks at three generations, right? It looks like Churchill and his father, and then obviously Churchill and then Churchill and his son. It's a great book. I thought you might like that one. Have you read any Stockdale?

[Sean Ryan]

No, I haven't.

[Ryan Holiday]

All right, so this is Thoughts of a Philosophical Fighter Pilot. So Stockdale goes to the Naval Academy in 43, graduates, becomes a pilot. And it's not until he spends 20 years as a pilot. It's not until the Navy sends him to Stanford, where he gets a graduate degree, that he's introduced to Stoic philosophy. On his last day at Stanford, his philosophy professor goes, hey, I think you might like this book. He gives him a copy of Epictetus, the Stoic philosopher. And he does two more deployments there before he gets shot down. And that's his sort of. Every night in his bunk on the. On the Ticonderoga and the Constellation, and a little bit on the Oriskany, he's reading Stoic philosophy. So when he gets shot down in 65, he famously says to himself, I am leaving the world of technology and entering the world of Epictetus. And it's in the Hanoi Hilton that he basically takes Stoic philosophy, which was a sort of theoretical thing, and he applies it in this, what he calls the laboratory of human behavior.

[Sean Ryan]

Holy shit. Did you get to meet him?

[Ryan Holiday]

I see I never got to meet him. He died. Yeah. I think he died in 2008 or 6. What does it say?

[Sean Ryan]

He died in 2006 at the age of 81.

[Ryan Holiday]

Yeah. No, I met his children and met a lot of people that have met him, but just. I mean, one of the greatest Americans ever, man. Incredible book. You'll love that. I was just. I. I'm actually doing a book on Stockdale right now. And this is. Do you ever read the Wright stuff? The Tom Wolf book?

[Sean Ryan]

No.

[Ryan Holiday]

Oh, you would like that, too. So that's about test pilots who become the first astronauts. So it's about John Glenn and Chuck Yeager. Really good. But this is about. There's a little stock down there, too. This is, like, about carrier pilots in Vietnam. Not enough people know about this book. It's incredible. It's called over the Beach. It was Stockdale's favorite book about the air war in Vietnam. And then the guys that get shot down. So I just read that. I think you would like that. If you don't read a lot, I think you would like that book.

[Sean Ryan]

Perfect.

[Ryan Holiday]

And then the last one. You ever read any Hunter S. Thompson?

[Sean Ryan]

Yes.

[Ryan Holiday]

Okay, so Hunter S. Thompson we think of as the badass wild man, crazy guy. You think Fear and Loathing in Las Vegas is a book about drugs and alcohol. Which it is, but it's the subtitle of that book is about the American dream. Because he's also one of our most astute sort of cultural and political writers. And so this is Freak Kingdom, and it's about Hunter S. Thompson as a political thinker and critic. Because he covers Nixon, he covers Carter, he covers every presidential candidate between sort of the late 60s and then his death. And I don't know, I got the sense. I think it would line up with where. Cause you're kind of like a man without a party. You're politically engaged, but you're not like, Democrat, Republican. I think you'd like that book. What he's primarily is anti fascist. Not like antifa, but anti fascist. Like, doesn't like fascism. Doesn't like people telling him what to do. Doesn't like liars, doesn't like hypocrites, doesn't like corruption. And I'm not gonna met this guy. I think you're gonna like it, man.

[Sponsor/Ad Voice]

Thank you.

[Sean Ryan]

Yeah.

[Ryan Holiday]

Yeah.

[Sean Ryan]

Thank you. This will keep me busy.

[Ryan Holiday]

Yeah, I think so. I appreciate it. I could have brought more. So my wife and I have a bookstore outside Austin. And so my favorite thing is when I'm gonna meet someone or someone Comes in, like, what books would I think they like? That's what gets me excited. So those are ones I thought you'd like.

[Sponsor/Ad Voice]

Thank you.

[Sean Ryan]

I really appreciate that. I'm actually, I want to talk about this one later.

[Ryan Holiday]

Okay.

[Sean Ryan]

Fatherhood segment done. This is something I talk about all the time with a lot of, a lot of different people, how they do it, but. Well, my gift is not as exciting, but this is the Gummies, the Vigilance League, Gummy Bears. Legal in all 50 states, made in the USA. All right, horrible for you, but they taste amazing. So. But let me give you an introduction here real quick. Ryan Holiday, author of 12 books on Stoicism with more than 10 million copies sold, including the Obstacle Is the Way, Ego is the Enemy, and Stillness is the Key. You're the founder of Daily Stoic, reaching millions through books, podcasts, newsletters and YouTube. Your work is right in NFL locker rooms, special operations units. I can attest to that. And Silicon valley boardrooms. In 2025, you completed your four book Stoic Virtue series and launched a sold out world tour across Australia, Ireland and beyond. Welcome to the show.

[Ryan Holiday]

Yeah, thanks.

[Sponsor/Ad Voice]

And so we have a Patreon account.

[Ryan Holiday]

Yeah.

[Sean Ryan]

And it's turned into quite the community. And to be honest, they're the reason I get to sit down here with you today.

[Ryan Holiday]

All right.

[Sean Ryan]

So they get the opportunity to ask every single guest a question. This is from Corey Smith. Ryan, for people battling anxiety, depression, or the long recovery from a brain injury

[Sponsor/Ad Voice]

when the brain can feel like the

[Sean Ryan]

obstacle, how can stoic principles be applied most effectively?

[Ryan Holiday]

Ooh. I mean, I can speak more to the first two than the, than the brain injury. That's not something I have direct experience with, but I think basically what stoicism is at its core is this kind of distance between you and your thoughts. Right. This is similar to Eastern philosophy, but it's the idea that you have the opinion, you have the feeling, you have the dread or the anxiety or the worry or the frustration or the anger. And you're trying to take a second and ask yourself, is this true? Right. Like you're worried about this thing happening and what you're not stopping and thinking is like, hey, is my worrying about this affecting the outcome in any way or am I just torturing myself? Right. You're not asking yourself, hey, let's say it does happen, what then? Right? Because oftentimes what we're torturing ourself with is this kind of vague idea that like, oh, if this happens, that will be bad and I won't be able to handle it. But the truth is, we handle stuff all the time. We've handled everything in our lives up until this point, or we wouldn't be here. We survived everything in our lives up until this point, or we wouldn't be here. And so stoicism is. It's funny he or she said about your brain is the obstacle. Sometimes the brain is the obstacle, injury or not. We have biases, we have patterns, we have things that we make up, and they're not true. Right? It's based on things that we haven't really worked through. And stoicism is the idea of kind of working through that. And that's, again, what Marc Stroz is doing in the Meditations. It's not like this magical formula that as soon as you hear it, you don't have that problem anymore. It's the Hamanopausen. Think about this and work through it and decide whether I'm going to assent to it or not. Epictetus, who's one of the Stoke philosophers, he would talk about how, he says a good money changer, a person you would get money from in the ancient world. He said, they know how to tell a counterfeit coin from a real coin by banging it on the table. They don't have to melt it down to test them out. They just know. You have that intuition. You just know. And I think what stoicism is, whether you're doing it in journaling, whether you're taking a few minutes, whether you take a long walk, or you're just talking through it with someone you know. Stoicism is about asking yourself, hey, is this real or not? Is this true or not? Is this productive or not? Is this helpful or not? Again, this is all very easy to say, but that's what it is as a process is to deal with precisely those feelings, which every person ever who ever lived has struggled with in some way or another.

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[Sean Ryan]

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[Sean Ryan]

When I research, when I. And I haven't gone that too far into my research in stoicism, but, you know, when I first left contracting for the agency, I was at social anxiety. A lot of people thought I was stoic. I just didn't like, you know, I just didn't like being in public talking to new people. And so I bottled everything up. And, you know, when I read some of these books and. And start digging in, it kind of feels like I would go back into bottling it back up. So what I'm. I just want to ask, you know, what's it. Where's the release valve in stoicism?

[Ryan Holiday]

Yeah, it's not bottling it up. I think. I think, obviously the word stoic in English, like, so stoicism comes about the 4th century B.C. this. This guy named Zeno from founds this school of philosophy. He's inspired by the cynics, another word that we don't do great justice to in the English language. We think cynics or cynicism means sort of negative or skeptical or, you know, doesn't believe in anything not what it is at all. And stoicism is called stoicism because Zeno sets up his school on the Stoa pokele, the painted porch in Athens. Stoa just means porch. These were guys hanging out on this porch talking about these ideas. Now, flash forward 2,500 years later when we go, oh, that guy is really stoic. We take that to mean, like, he doesn't feel anything. He's a robot. He stuffs it down. And that's not what it is at all. To me, it's about processing that emotion, asking yourself, hey, is this productive or not productive? Is losing my shit about this? Is that helping anything? Or is it, in fact hurting myself, other people making the situation worse? So it's not like, hey, I'm feeling an emotion. Emotions are not okay, let me white knuckle it. To me, it's about asking yourself, working through it, hey, why am I feeling this way? What is this doing for me? And then I think your question about where's the release valve? Is a good One, because to me, I find that release valve in the work and usually in some kind of physical activity, I think you got to have outlets for it. But the idea of just getting to a place where you're pretending it's not happening, like grief, if you just go, oh, I don't feel that. That's not real. We have multiple stories about Marcus Aurelius crying, right? The most famous stoic in the world that we don't have that much. Like, the historical record is relatively thin on this person. We don't have that many stories about him, right? And I think there's four about him crying. One is over the loss of a tutor. Like, one of his favorite teachers dies. Another is when he's told he's going to become emperor. He. He's just so overwhelmed at the weight of the job, he doesn't think he can do it. And then two others are about the victims of the plague. Marc Aurelius is the Emperor of Rome during what's called the Antonine Plague, which is this devastating pandemic that kills millions and millions of people. And then another is when he's told that an earthquake has flattened this Roman city. And so, like, in all these cases, he's not stuffing his emotions down. In fact, in the first story about the beloved teacher, you know, he's trying to not feel the emotion. He's like a young kid, and, you know, he probably. Some of the ideas of masculinity that we all know, you know, like, boys, don't cry. Don't be a little bitch, right? Like, he's not. He's clearly upset by the fact that this person he loves has died. And one of his philosophy teachers goes to him and tries to tell him, let's keep it under wraps, kid. And his stepfather, who's the emperor of Rome, Antoninus P. He sees this and he goes, no, no, no, no. He says, let the boy be human. And so stoicism to me is not. You never have the emotion or that you stuff it down. I think it's more like, okay, look, if you're still paralyzed by this grief a year later, you can't get out of bed. That's a problem, right? To me, it's the processing, the passing of the emotion, and then it's getting back to center as quickly as possible. That, to me, is what the philosophy is.

[Sean Ryan]

Okay. Yeah. I think this book here, Meditations, is going to be very interesting.

[Ryan Holiday]

I think you'll like it, because I just

[Sean Ryan]

does seem. It does feel like kind of stuffing your emotions. What you're saying makes me thinking before acting. But really, you know what really got me into it as I've started bitching all the time.

[Ryan Holiday]

About what?

[Sean Ryan]

Just bitching about. I mean, I'll just be honest. I haven't been happy with the last two administrations. Sure. But at all. And I feel like I really got duped on this one. And you know, and so I want to be more solutions based and focus on actual solutions than just do what everybody else does. And yeah, let's about all the problems. Let's about the Epstein files, let's about the wars. There has to be. Let's about the stuff that we've been bitching about for, you know, ever.

[Ryan Holiday]

Yeah.

[Sean Ryan]

And at least as long as I've been around. And there's just very few people that take the time to take the things that make them angry and come up with real focused potential solutions.

[Ryan Holiday]

And it's important. One of the things you hear the Stoics talk about is like getting some perspective, right? Like, none of this is new. So Seneca is one of the famous Stoics. Do you know who his boss was? Was Nero. Like, his boss is the worst leader maybe of all time. Right. And I got to imagine this is stressful. I imagine it's demoralizing. I imagine there's a lot to bitch about. Like, in a way, none of this is new, right? Corruption's not new. Hypocrisy is not new. Declining empire is not new. The only thing that's new about any of this is is that we have a lot more information in real time about what's happening, right? Like it was possible to get away from it in the past in ways that we can't now. It was also worse in the past in other ways, right? Like, you know, no one's being forced to fight for their life in the coliseum, let's say, right? There's definitely some things that are better. But like I think about even Socrates, right? Socrates, you know, you think, oh, that was that guy, he wore the toga, he walked around Athens, he asked those questions. Must have been pretty chill. And it's like Socrates lives through the Peloponnesian War. Athens fights a generationally long war against Sparta and loses his country, loses a world war, effectively. And then Athens is ruled by 30 tyrants. Literally, it's known as the time of the 30 tyrants. I mean, like, the world must have felt like it was falling apart and it was falling apart. And so I think one of the things you can take from the study of history and I think we all need to study history more, right? Like, people. Like, people watch too much news and don't read enough history. And the reason for this is, like, they think that being that their job is to be an informed citizen, and it is. Your job is to be an informed citizen in America, in any democracy, the problem is watching news in real time is not necessarily the best way to be informed. And so I urge people to read more history. Not because it takes anything away from the moral calamities that are happening in this moment, but it allows you to understand them in context. It allows you to understand which ones are really important and which ones are kind of par for the course. Right? And it allows you to also remember that, like, no one has lived in a perfect society and that most of the people that you admired were looking around at the world and going, what the fuck are we doing? This is insane. You know, Like. And that actually the job is to not despair, not to get into, like, bitterness and anger, not to. Not to. Like. One of the things Marc Charost talks about in Meditations, he has. He talks about revenge a lot. You can imagine the most powerful man in the world, if he wants to get revenge on someone, he can. He can do some pretty heinous things to people. But he says, you know, he tries to remind himself, the best revenge is to not be like your enemy. And one of the things, I look out at the world and I go, I don't like the corruption, I don't like the cruelty. I don't like the dishonesty. I don't like the pettiness. I don't like the crassness. I don't like any of this. Now, obviously, as a citizen, my job is to vote against those things, speak out against those things. But my main job as a person, philosophically, is to not be those things, right? Like, if what you allow is the shittiness of what's happening around you to make you feel shitty and worse, to be shitty, like, they are winning. And so I think that's. To me, that's where stoicism really has a lot to offer, because we are living in disorienting, disappointing, disillusioning times. But if you allow that to strip from you your happiness at home, your productivity at work, your decency, your kindness, your connection to other people, like, it is winning. And that's. That's kind of how I think about it.

[Sean Ryan]

I mean, how do you. I'm curious too, because, I mean, it's. You know, I brought up. I brought up politics.

[Ryan Holiday]

Yeah.

[Sean Ryan]

But there's there's just so many other. And I think that's something that everybody can relate to one way or another. Right?

[Ryan Holiday]

Yeah.

[Sean Ryan]

But, I mean, we're going to talk about this, you know, towards the end of the interview, and I guess we'll talk about a little bit right now. But, you know, as you find success, you also find very disingenuous people that start to come around and they want to take advantage of you. Sure. They want to take advantage of your kids to get to you. They want to take advantage of your wife to get to you. They are not honest people, you know, and you threw out the word revenge, you know, and that's in my mind. I mean, revenge used to be something that, I mean, I would waste an entire day planning all the things that I could do to somebody that took advantage of me or wronged me or, or over my family or myself or whatever. Right. Whatever the circumstances are. And then I, you know, back in the. A long time ago, I would act on that. This is the best plan. We're going to do this. And then I, you know, and then I realized this is just a total waste of energy.

[Ryan Holiday]

Yeah.

[Sean Ryan]

And it just makes you look like an. I think. And so now I'll. I can't help myself a lot of times.

[Sponsor/Ad Voice]

And I will still go through the

[Sean Ryan]

planning phase on what I could. What can I do to get back at this person? And then I've developed one where somehow I've developed enough discipline to never act on it. That's a good first step, just to let it go.

[Ryan Holiday]

I imagine it if there's an extra level of not temptation, but where you're like, I could break this person in half. You know, like, that's not a thought that enters my head. But I imagine when you are trained to do what you are trained to do and at different points in your life, that has been unleashed just the restraint of going, hey, that's not the rules of engagement. In the world that I'm in now, that would be like, a level of, like, restraint that you would have to practice. But one of the things I think about is like, okay, if somebody tried to control my thoughts or controlled what I said or controlled what I did, I'd like, I'd resist that, like, just instinctively. That's no, I get to decide. I'm in charge. And yet we kind of hand our minds over to people all the time. Like, we let them. We let them just take up, like, inordinate amounts of time and space in our life. I was talking to this Talking to this writer I know, and she was saying, you know, she really didn't like what was happening politically. And she was saying that she was having trouble. She was like, I just can't. I can't work right now. Like, she's like, I'm so outraged. I'm so upset, so pissed off that, like, I just. I can't. I can't do it. And I was saying, like, okay, but, like, if this administration came to you and was like, hey, if you keep doing your work, we're going to throw you in prison. You'd be like, that would be so immediately galvanizing that it would fire you up. Right? You would never allow a government of any persuasion to tell you what you can and can't say. That's the job of an artist, and that's what it means to be an American. That's what it's all right there in the First Amendment. And I was like, but here, voluntarily, you're doing precisely that because you don't like what's happening in the world because it's dark or pissing you off or whatever. You're allowing it to consume so much of your mental bandwidth and your motivation that it's having the same effect. Like, they might as well be putting a gun to your head and saying, you can't do this, but it's actually worse because they're not doing that. And so I do think it's really important that we. You gotta have some mechanism by which you put up some walls and boundaries, and then you protect the thing that is yours. The Stoics would say, the greatest empire is command of yourself, your sovereignty as an individual. And the problem is, we give that up all the time because somebody cut us off in traffic, because we opened up our phone and the news was bad because our parents are visiting or, you know what? Like, we just let these things get inside us and then determine our mood, determine our, you know, our focus, determine what we think about, determine our behavior. And, I mean, it's not easy. It's a lot of work. And I fall down this, you know, sort of into these traps all the time, but I am trying to go, hey, like, I got to protect this. Even. Even if it feels good or feels natural, I can't allow that.

[Sean Ryan]

Have you ever done psychedelics?

[Ryan Holiday]

No.

[Sean Ryan]

Okay. Reason I'm asking. Yeah, I have. I did. I did a ibogaine treatment in Mexico four years ago. I haven't had a drop of booze since. Been a lot more in the moment. It was very. It was a Life changing experience for me anyways. The reason I bring it up is it's, it's.

[Sponsor/Ad Voice]

There's been very few times in my

[Sean Ryan]

life where I've been able to completely separate myself from, I guess maybe my ego and look at things from a. Just a detached point of view. That's maybe a different perspective than what I'm feeling in the moment.

[Ryan Holiday]

One of the things that I, I did this like really intense therapy thing and I was, I was, you know, sort of like just vomiting all this anger and resentment I had at these, this group of people. And the therapist was like, you know, they're not thinking about you at all. Right? And, and he was like, they're just doing their thing. That's who they are. They have no awareness. Not only are they not doing it on purpose, but like they're utterly unconcerned and disinterested of its effect on you. Like they're not waking up and thinking about torturing you in this way. They're not waking up and thinking about abusing you in this way. They're not waking up and trying to make you miserable. They're inherently selfish, narcissistic people. They're waking up and thinking about them. He's not saying it's awesome to be them, he's just saying they're not thinking about you at all. And it's like we can see this, I think, much more clearly in other stuff, like the economy's not thinking about you, A hurricane's not thinking about you, that truck barreling towards you on the freeway is not thinking about you. But then for some reason, because people do have intentions and obviously we have to be aware of them, we do, I think, project a lot more intentionality on other people than is actually happening. And I think when you have someone who's like, like way inside your head reminding yourself that you're not inside their head is really important. And then I like you all, sometimes I'll be like, I just planned out like a whole operation in my head of what I'm going to do if they do this. And it's like, this is a hypothetical. My whole run I was thinking about what I'm going to say if they say this and then I'm going to say this. And it's like, this conversation might not even happen.

[Sean Ryan]

Contingency planning.

[Ryan Holiday]

Yeah. For a made up scenario about a person that again, if you ask them, you're like, they'd be like, who? Like, they wouldn't think about me at all. And so it's like you're not the center of the universe, and almost certainly you're not the center of whatever the situation that you're making all about you is, makes sense.

[Sean Ryan]

Also where I was going with that is. Is stoicism, the ability to kind of view things not as a participant of what's happening. It's just a. Strictly in observation or observing a situation.

[Ryan Holiday]

Yeah. It's like, sometimes it's really helpful to zoom way in, and then sometimes it's helpful to zoom way out. But it's like, a lot of times it's like, how do I take myself out of this equation?

[Sean Ryan]

Okay.

[Ryan Holiday]

And that I. That's what ego does. Right? Ego makes it all about you. It makes you at the center of things. And even just remembering that, like, everyone is the center of their situation, and that, like, you're not the main character in all these other people's stories, you're the tangential character at best, is. Is helpful. Yeah. Why. Why am I making this all about. Like, this was not. Whatever this was, was not specifically chosen to drive you nuts. Like, like. And that again, it's, it's. It's totally indifferent to you. Like, one of the ideas for the stoics is events are objective, our opinions about them are not. The situation is what it is. And then we say this is good or bad. I don't mean morally positive or negative. We say this is fair or unfair. We say this is mean or cruel. We say this was targeted. We say we've been harmed by it. The thing is. And then we decide what it means. And a lot of times the stories we tell ourselves about stuff are pretty self absorbed, pretty distorted, and, like, pretty emotional. And I think, how do you get better at going, what if I could see this from another perspective or another way? Or, what if I told myself a different story about this event?

[Sean Ryan]

Yeah. What happens? I mean, what goes through your. When I told you, you know, oh, I'll spend an entire day planning revenge or vengeance? What happens in your head when you're wronged, when you think you've been wronged, when somebody's.

[Ryan Holiday]

Well, often at times I go, okay, let's say I pull this revenge off. In all the times in my life when I have done it, how did I feel after?

[Sean Ryan]

Pretty shitty.

[Ryan Holiday]

Yeah. Shitty. Or at best, disappointed. You know, and why am I telling myself it's going to be different this time? And the idea of thinking about what you're going to think after is like a really powerful way. Do you know, you know the word Epicurean? I don't that was the rival school to the Stoics. There's the Stoics and the Epicureans. And Epicurean, also in English, tends to mean, like, love's pleasure indulges every whim. And that's not really what they thought at all. But Epicurus, what he would say, he was, let's say, more pleasure seeking than the Stoics. He would say, though, like, if you're going to. You're like, hey, let's share this bottle of wine. He's like, you can't think about just how it's going to feel on the way down. You have to think about how you're going to feel after. And that part of the experience has to be put into the calculation. Okay, but humans are bad at this, right? We tell ourselves, oh, if I make this amount of money, then I'll feel secure and good. If I get with this person, then I'll feel. It'll be amazing. And then I'll feel good and people will look, if I get this car, if I win this office, if I hit this number on the chart, like, we, we just, we tell ourselves this lie that, like, this thing will do something for us. Now, the first time or when you're younger, we can excuse this because, like, we don't have. Although there's all sorts of wisdom out there telling us that it's not going to do what we think it's going to do for us, we don't. We haven't directly tested the hypothesis ourselves, but I think as you get older, to still be falling for that lie is a problem. Right? You know how you feel when you have a hangover. You gotta take that should change the drinking that you do. You know that. I don't know. Your marriage is incredibly important to you and certainly not worth a few minutes of pleasure. And yet you in the moment are considering doing something that would blow that up. Or, you know, all your other accomplishments have never made you feel secure or like you've arrived, that there's an emptiness or a hollowness to them, and yet you go, it's different this time. Why do we.

[Sponsor/Ad Voice]

I mean.

[Ryan Holiday]

Yeah, well, I think from an evolutionary standpoint, it makes total sense, right? Like, if humans were good at being like, I'm good, I don't need any more. Like, enoughness is not a great evolutionary feeling, but, like, insatiability makes you go on to the next and the next and the next thing. And so that can be good for the species as a whole, but really bad for the individual. Makes sense. I Think it's. We are not designed to. Our biology is not inclined to make us feel content and happy and secure. And it takes a lot of work to counteract that impulse.

[Sean Ryan]

How have you done it?

[Ryan Holiday]

I mean, I struggle with it like everybody else. I try to walk through this process like, how am I going to. It's not that. To me, going, like, okay, hey, if I get on the other side of this, this accomplishment, this achievement, whatever, it's not going to make me feel. It's not going to magically fill some hole in my soul. That doesn't mean it's not worth doing. I can find other reasons to do it. It's challenging. It's interesting, you know, it's beneficial to people around me. Like, there's other reasons to do it. So I. And then what I find is that if I'm doing it for those different reasons, the outcome, if I'm lucky enough to get it, I feel differently about it, too, because there's not a false expectation that was impossible to meet. But I think. I mean, I. I'm constantly trying to stop and go, why do I keep finding myself in this same. Why don't. You know. And the definition of insanity is trying the same thing over and over again, expecting different results. That's kind of the human condition. And I'm like, why do I keep sort of backing myself into this corner, finding myself going down this lane? And then I'm like, I know better than this. I'm doing it. I think I'm doing it better than I was when I was 19. But, like, I'm still doing some version of it. And I think that's kind of. We're all battling these kind of scripts or these patterns that we picked up on in our lives, and we're. We're trying to get a little. Trying to get a little better at it as we go.

[Sean Ryan]

Yeah. It reminds me of the saying, nothing. Nothing's what it's cracked up to be. But. Well, how did you get into this stoicism about your interest?

[Ryan Holiday]

Yeah, it's funny. I was in college, I was taking a philosophy class, and then I went to this. I went to this conference. I wrote for the college newspaper, and I asked the guy who's speaking, I said, like, hey, you got any book recommendations? And he was like, you know, I'm reading this guy Epictetus. I think you would like it. And I ended up getting. Somehow I forget how, but I ended up with Marcus Reelis instead, probably because I saw the movie Gladiator and I opened this book. And I go, what the fuck has this been? You know, like, this is what. Like this exists. Like, this advice is there. Like, and it kind of just. It kind of just turned my world upside down.

[Sean Ryan]

How so?

[Ryan Holiday]

Just that I think all young people, anyone coming of age but men, especially in this world, are looking for, like, the path. Like, what should you do? What should you not do? And they're looking for it in a way that school doesn't address. They're looking for it in a way that the church doesn't address. I mean, especially, I think, in some ways, like, you know, some sports programs and definitely maybe like a military tradition. It is based on certain values and you're being inducted into a way of life, right? But if you don't have that, you go away to college and they're like, you can do whatever you want. You can be whoever you want. You can do whatever you want. If it feels good, it's right. You just have effectively unlimited choice. We live in a world religion used to go like, hey, don't do these things or you'll go to hell. And I think obviously that puts a lot of fear and shame and control on people. That's not good. But the problem is when you. When you say, hey, do whatever you want, nothing's wrong, everything's right. Trust your gut. You know, like, the last thing a 19 year old should be doing is trusting their gut. Like, you're an idiot. You know, especially, like a. Especially a 19 year old dude, you know, like. And so I think what struck me about stoicism was like, oh, this is a 2, 500 year tradition. This is a tradition that's been followed by the most powerful people in the world, some of the most powerless people in the world. Epictetus is a slave. And these are people that were dealing with uncertainty and chaos and disorder and dysfunction. They were dealing with temptation, they were dealing with adversity, they were dealing with loss and pain. And hey, they wrote some of their experiences down and they put it into a framework that is actually strikingly modern. Let's just say it's timeless. And I think that's what. Sitting at the table in my college apartment, I was like, oh, okay, like, this makes sense to me in it.

[Sean Ryan]

At 21, you were the director of marketing for American Apparel.

[Ryan Holiday]

Yeah.

[Sean Ryan]

How did that happen?

[Ryan Holiday]

An insane. I mean, it says more about the company than it does about me. You know, it was a dysfunctional, crazy, you know, show, really.

[Sean Ryan]

But, yeah, it got to be a huge company.

[Ryan Holiday]

It was. I mean, it was a huge Company. When I, when I started there, I had nothing to do with it becoming what it became, but I got sort of thrown into the deep end. And yeah, it was, yeah, my 20s were nuts, but I, I watched a, you know, a guy create a billion dollar company and then destroy a billion dollar company. And I watched people get caught up in it. I watched people get sort of spun sideways by it. I watched people enable it. You know, I enabled it. And so I, you know, in a way it was like, it was, it was quite an education in. I mean, it was like, it was like a king's court. Like he was the sort of king and everyone was, you know, currying favor and wanted something. And, you know, it was, it was a. It certainly informed like what I ended up writing about a lot.

[Sean Ryan]

And at 25, you wrote, Trust me, I'm lying.

[Ryan Holiday]

Yeah.

[Sean Ryan]

Where did that come from?

[Ryan Holiday]

It was also, you know, American Apparel was one of the sort of most controversial companies in the world at that time. And so, you know, I had sort of a window seat to how the media environment worked. And then I worked with a number of other sort of controversial clients and stuff over the years. So I wrote an expose on sort of the media system and marketing and pr. I mean, I basically wrote a book on fake news in 2011.

[Sean Ryan]

That's what it seems like.

[Ryan Holiday]

Yeah. Yeah, I thought. The funny thing is, I thought, I thought. I remember trying to get the book out as quickly as possible, going like, this is right now. And if anything, I was probably 10 years early, but I was watching how like the sausage got made, right? Like how true stories got distorted and how made up stories became true and how people could get attention, what attention would do to people, the incentives of the media system. And so the book was me kind of trying to rip back the curtain on what that was and how it worked.

[Sean Ryan]

Can you go into it a little bit?

[Ryan Holiday]

Yeah, I mean, it's, it's funny because, I mean, I wrote that book because

[Sean Ryan]

it is, it's now.

[Ryan Holiday]

Yeah, but it's funny. It's like, you know, I wrote that book Before TikTok existed, before, before I think maybe Instagram had just come come out. I was writing mostly about a world of blogs and, you know, sort of not traditional media, but like traditional media as it was being intersected by social media. And I mean, if anything, just all those trends have accelerated now. But it was ultimately what I'm trying to say in the book is like, you have to think about the incentives operating on both sides of the equation. The people that are trying to get messages out and then the people who are communicating those messages and that everyone is effectively competing for attention in this enormous ecosystem or this marketplace. And so in a world where it used to be okay, half the country subscribes to the New York Times, half subscribes to the Washington Post. Now both these papers have an agenda. There's a bias, but mostly they're trying to deliver value for the subscribers of the, of this paid product. And they're putting out a 40 page newspaper where once you buy it,

[Sean Ryan]

all

[Ryan Holiday]

the information is there. If you look at the headline in the New York Times for the Pentagon Papers, it's like there's no sensationalism in it. There's no craziness because you're not buying the New York Times in Grand Central Station with a newsboy shouting, extra, extra. Read all about it. We're. Which was the media environment in the late 1800s and the early 1900s. And so basically what the Internet did is it broke all that apart and it made it so every story, every headline, every article, every clip is competing with everything else out there, right? So it's like what's the craziest? What tells people what they want to hear, what pisses people off, right? What offers the most certainty? That's what draws like an analogous way. Like what happened in the early to mid 2000s is akin to what's happening now with podcasts, which I'm sure you've experienced, which is like there was this period where podcasts were long form interviews that subscribers of that podcast listened to, right? So you have all the subscribers to this show and you think about like delivering high quality guests who you have a long form conversation with and people listen to the whole thing. And then what's been happening the last, I don't know, two years is like the sort of the clip economy, right? Where now it's like about the most sensational clip. So that two hour conversation is distilled down into a 20 second clip or whatever. And what that's doing is creating, as I'm sure you're seeing it with peers of yours, is a lot of competition for the craziest clips. Gotcha moments. Or conversely, you're just having the same conversation, but then people are coming and cutting out those clips and spreading them. And so now it's creating a lot of pressure and a lot of noise and changing the incentives of the medium. And so what I was writing about, and trust me, I'm lying, was that sort of first wave of that happening where now you don't read a website. You read articles from that website. And you only read them because it's showing up in your Facebook feed or it's showing up in Twitter, or it's because somebody emailed it to you. And that's creating an incentive, a bias towards certain kinds of emotion. Like, for instance, they found that the valence of the extremeness of the emotion is the number one predictor of virality. So something that makes you feel pretty good is not going to be shared as something that makes you extremely angry, or something that makes you kind of angry is not going to spread as well as something that makes you laugh really hard. And so it's creating this incentive for extremes, right? So everything becomes an exaggerated, distorted version of itself to meet that. And then you layer on top of that, in the sort of blog world, one of the first kind of big breakthroughs was like, reporters or influencers or

[Sean Ryan]

whatever,

[Ryan Holiday]

your job performance was, like, how much traffic your article got or how many views your video got, right? Which is different than how journalists had basically been paid for the entirety of the institution. And so in the same way that you wouldn't want a journalist to own shares in a stock that they were reporting on, now they own stock in the story. Instead of being like, hey, it's complicated and we don't know which isn't going to do well, they're like, it shapes the story that they're writing. And I think what we're seeing now, now that people are working for outlets less and less and working for themselves more and more. Like, are you going to tell your substack audience what they don't want to hear? Are you going to have a guest on? Like, not you, but, like, you can imagine someone in a different financial position. You're like, hey, when I have these kind of guests, my Patreon numbers go down. And when I have these kind of guests, my Patreon numbers go up or donations go up when I do this, and they go down when I do this. And so now, again, these financial incentives are acting on the information that people are getting. And people are not good at evaluating the reliability of the person. They're getting information. We're just really bad at it.

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[Sean Ryan]

I think we've lost that because I think that the thirst for real information has significantly, significantly diminished because now people are more concerned with confirming their opinions and their own thoughts. And so rather than actually search for some kind of truth or really try to figure out what the hell is going on, what's at the bottom of this, instead of doing that and spending the time to research and hear other opinions and perspectives, they immediately sift through everything they possibly can to find the one person that is gonna tell them everything that they're thinking is correct. And then it turns into, they tell them how to think, and it's become like this lazy search for just confirming your own biases, opinions, and thoughts.

[Ryan Holiday]

Yeah. And there's always gonna be someone who will fill that need. So, like, we saw this, like, in the aftermath of the 2020 election, right? It's like, oh, if you're not gonna. If you're not gonna tell the audience what they want to hear, then they're just gonna go watch this channel. And if that channel isn't gonna do it, they're gonna watch this channel. And so it's. It's hard. Like, choice is good, but the problem with choice when it comes to information is that you're creating a market incentive for people to lie to you. And typically that incentive is mitigated or by the fact that the media outlet is owned by a big company or the reporter themselves is a salaried employee who identifies as a journalist or a writer, whatever. It's different when it's like, no, no, no. Like, I write for Substack, and I am directly dependent on how many subscribers I have paying subscribers. So, like, audience capture, there's fewer intermediaries between the creator and the sort of payment structure. Now, in many ways, this is great for creators because there's fewer people taking, you know, pick in their pocket along the way. But it also Means that they are directly exposed to some perverse incentive. Like audience capture is right there, there's an influence. Yeah. And like it takes a person, it takes some character and some self control and some ideals to be like, no, no, no, no, I, I, I have an audience. The audience doesn't have me. Like, I say what I think needs to be said, not what's going to do. Well,

[Sean Ryan]

that's what I try to do. I think that's what you do too.

[Ryan Holiday]

Yeah.

[Sean Ryan]

I mean, do you think that. Because I've always been more of a long game person than, than a short game. And so I see exactly what you're talking about all the time. And I would say that the majority of those people don't last very long. Eventually it patters out. And, but by being, being true to yourself and not being beholden to an audience or financial incentive or whatever, I mean, you're going to do this and it's a fucking roller coaster.

[Ryan Holiday]

Yeah, yeah. They're outraged about this and then. Oh no, no, we're not outraged about that anymore. Now we're outraged about this and no, no, actually I like you're surfing the audience and it's both exhausting and also it just doesn't feel like success to me. Right. Like, if success is like, I have to tell you what you want to hear, then like I work for you.

[Sean Ryan]

It's boring anyway. I mean, just to sit in here, I mean, I get a lot of people pissed at me right now because I've leaned across the aisle, because I like new perspectives. That's how shit gets done, you know, and, and, but I just don't, I just don't fucking care, you know? So I'm like, this is what I'm gonna do. I'm just, you're, I'm not gonna be beholden to anybody on who I talk to and do not talk to.

[Ryan Holiday]

Yeah.

[Sean Ryan]

And, and I, it's boring to me to sit there and talk to somebody that has the exact same opinion to me over and over just to confirm to each other that we're, we're the, we're in the right way of thinking. But I'm curious how you navigate it, because when I started this thing, it was just military guys and intelligence folks and people that I'd worked with in the past. And I really just wanted to correct the record and actually have people that had been in the events that these reporters were talking about. Well, actually, here's what actually happened from a guy that was there, you know, and then we started talking about political Issues, Issues with kids. Like lots of different problems that society faces. And it would be a discussion inside one of those.

[Ryan Holiday]

Yeah.

[Sean Ryan]

And then to make a bigger impact, I actually started going to the, to the, to the lawmakers, you know, to the people in charge, people that can make a difference. And, and then I realized they all just lied to you, you know, and they use the platform to, to advance themselves. And so now, now I'm extremely particular. I even have friends that are running for Senate, for Congress, for whatever places in the administration. Doesn't matter.

[Ryan Holiday]

Yeah.

[Sean Ryan]

You know, and I won't have them on.

[Ryan Holiday]

Interesting.

[Sean Ryan]

Because I just. You're just gonna tell me what you think I want to hear and what I think my audience. What you think my audience wants to hear.

[Ryan Holiday]

Yeah.

[Sean Ryan]

And then even if you do have great intentions, I've seen it too many times, you're gonna get in there, you're not gonna make an impact. You're not going to. They're gonna own your ass. You're not gonna be put on committees if you go against the grain. And you're just gonna turn into the same shit that we see every single time. But if you do hold true to your word, I'll help you with your re election.

[Ryan Holiday]

Yeah. You know, that's interesting. Yeah. I think deciding, deciding what you're gonna be a part of and not be a part of to me is like what it's kind of all about. And I think I've been amazed at the degree to which people I know don't think about like, hey, is this a good person? Do I agree with them and just not to agree with them, but like, are they a bad actor? Or, you know, someone at least operating from good faith and they just think about like, how's this gonna do? You know? And like to me, success and a platform comes with responsibilities. Not, not just like, hey, how do you look yourself in the mirror? But like, like people are. If they see you have someone on or they see writing about something or talking about something, like they assume that it's not a cosign. But you're, you're, you're, you're participating. Right. You're like, you're. They go, oh, they wouldn't have this person on if they were psychopath or a lot. Like people like, I, I just think there's a responsibility that comes from having a platform or having influence and it's a huge responsibility. Yeah.

[Sean Ryan]

People make decisions based off what, what's said in this room.

[Ryan Holiday]

Yeah.

[Sean Ryan]

Like life changing decisions.

[Ryan Holiday]

Yeah. Yeah. There's, there was, I Remember finding when I was writing, trust me, I'm lying. There's some, some. And it's funny, none of this stuff is new. There was this media critic and he was writing in like the late 1800s, early 1900s, and he says, America is a country ruled by public opinion. That's what a democracy is. And he says, therefore, what determines public opinion rules America. And so the people that own newspapers, yeah, sure, it's a for profit business, but like, they are responsible for something that in a way affects like the whole country. And that there has to be a response. He was saying there has to be a responsibility, that these things are kind of public trusts. And look, again, I think you get in real problem territory when the government is deciding, you know, like, I'm not saying it should be. Like, this isn't something that should be legally policed, but like, if the people with the platforms are not policing themselves, that's a problem, right? Because then basically, people without character, people with agendas, they can take advantage of that. You know, they take advantage of that. And we're so consumed in America by, like, our political disagreements that we forget that there's people outside America that are also trying to steer and navigate this discourse. Right? And just as, by the way, historically we have done that in other countries, but we seem to think that the only agenda someone could have is left or right. Not Russian, Chinese, Iranian. Like, our enemies see these gaping holes in our media system. They see these people who are basically available to the highest bidder, and they're like, do I want to go to a war with America or do I want to make America go to war with itself? And I think one of the things I was trying to write, and trust me, I'm lying, is like, hey, look, here's how I'm getting you to buy T shirts or getting you to follow this brand or this person or whatever. But real bad people can do these same things and in fact are doing these same things. And I think that, to me, though, even the craziest part of our system isn't just that bad actors can do it, but also the system can manipulate itself. Just like it's so primed for going to where the energy, the action is that sometimes things that start as jokes become real things or things that start as the most harebrained conspiracy theory that you could imagine becomes real. I live in this town called Bastrop, Texas, and one of the first ones that really caught my eye on this. Do you remember the Jade Helm conspiracy?

[Sean Ryan]

No.

[Ryan Holiday]

There was this conspiracy that, like, this is during this 2015. So it's during the Obama administration. They were doing like these big training exercises in like the south and the Southwest. And this conspiracy theory comes out that, like, it's actually this false. It's like this crazy operation where they're gonna, like, I don't know, the federal government was gonna like, occupy the Southern states. It was like a faux military training exercise as a prete. Like start a civil war or something. It was this conspiracy theory that starts online and starts on Facebook. And one of the exercises was happening in where I live. And the governor of Texas ends up sending the National Guard to observe the exercises to make sure this didn't happen. As if that could do anything. But anyways, the point was, it came out in the years after that this was mostly like a foreign sort of propagated theory that this thing, some crazy person online said this, and then it

[Sean Ryan]

was objected from a foreign influence.

[Ryan Holiday]

And then. Yeah, exactly. They went and they put energy behind. They put spend behind it and spread it and whatever. And so it was like, oh, okay. So again, we're so consumed with what we're doing to each other that we don't think about the fact that other people have an even bigger incentive to get us really focused on this or that. And so again, countries that are real close to Russia, like Finland, they spend a lot of time teaching media literacy to their kids because they know that it's real and they know that these operations and this agenda is right there all the time. And I think we live in a bubble because we've so often been the exporter of culture that we don't think about the ways that different nations, causes, etcetera, Have a vested interest in directing that culture in certain ways. And so that's one of the things I was talking about in the book too.

[Sean Ryan]

Yeah, I've. I mean, I've. Like I said, I've changed my tune since the last election. And you know, what I've realized is I think that the. You can have a better, bigger impact in just initiating. In how you initiate certain conversations rather than who you initiate them with. If you start the conversation properly and plant the seed, then it will grow. It will grow into what it needs to be instead of trying to hit the head honcho and pour your ideas into them and hold them accountable.

[Ryan Holiday]

Interesting. What do you mean?

[Sean Ryan]

I mean that. What do I mean? I mean that I've just. Everybody I've brought on here that can make an immediate impact that is in a position to make an immediate impact, they always fall short, no matter what they tell you. But what I have noticed is the things that. In my own personal experience with some of the discussions that I've had in here, the biggest impact that we've made is by starting a conversation and watching the conversation grow through regular people, through the population, not from getting direct to a president, a congressman, a senator, a CEO of a company, somebody that owns a nonprofit, whatever. It's the conversation that happens that engages the population has a much, much bigger impact than going directly to the decision maker.

[Ryan Holiday]

Have you heard that expression that politics is downstream from culture?

[Sean Ryan]

No.

[Ryan Holiday]

I think that's sort of what you're saying is, like, what matters is the consensus or the idea, like the energy, the vibe is more important than a single decision maker, which is, by the way, our whole system. We have a decentralized system where decision making is decentralized and widespread because the founders were so concerned about sort of man on horseback. And. And so there really isn't one singular person who can make a difference now. The problem is that has also allowed a lot of people who are in positions of power to abdicate their responsibility to make a difference. Right. Like everyone. Everyone is trying to save their jobs for some point in the future when they'll be the decision maker, you know, and, like, look, you do need those people, but chances are you're not that person.

[Sean Ryan]

Yeah.

[Ryan Holiday]

Like, chances are you should do the right thing right now.

[Sean Ryan]

Yep. It's interesting. It's interesting. I think. What do you think it is? I think it's addiction to power. But then looking at it from the outside, and it does appear that they have a lot of power. But then when you see it and you're like, you're. You're fucking completely powerless because you're not saying what needs to be said, even though you know exactly what the fuck you need to do. Because you want to hang on to the fake power that you think you have, but you're actually powerless because you're

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not saying what you know needs to

[Sean Ryan]

be said because you know you won't have that position anymore when that position

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[Ryan Holiday]

I think the difference here, there's power and there's status, right? And so they don't exercise the power because they want to keep the status. I mean, look, Thomas Massie is not going to be a congressman much longer. The irony is, when you meet a lot of these politicians privately, not only will they tell you a bunch of things that they won't say in public, but they will also tell you how much they don't like their job. They fucking hate it. It's a miserable job. They don't like their colleagues. They think there's a lot of performance and they have to spend all this time fundraising. They don't like the job. And yet when it comes down to these votes that seem to me to be very clearly conscience based or very stark moral choices, they're like, well, I gotta do what I know is wrong to keep this job that I don't fucking like. I'm like, I don't get it at all. It doesn't make any sense to me, right? But the problem is, I remember I was sitting in the Senate dining room talking to a senator, and I was saying, like, hey, why don't you guys. You and I probably have very different politics. But I was like, why don't, you know, this Trump thing is crazy. Like, what are we doing here? And I was like, why don't you speak out about it, you know? And he goes, see that guy over there? And he's like, yeah. And he's like, that guy was gonna be head of the CIA. And I go, okay. And he's like. And then I can probably say who it was. He said that the White House was like adult daycare over there. I think this is Senator Corker. And he's like, he's not even gonna be a senator anymore. You know, he was like, that guy was in line for the next office, the next level, and he made a comment and it's not happening anymore. And the guy was basically saying, like, that's why. And he was laying it out for, like, it is crazy because, like, me as a citizen, I'm like, you're one of the, you know, hundred most powerful people in the world, and that's not how they see themselves. And so I don't know, why would you want. And look, I write about this. I wrote this book on courage. I talk about when I was at American Peril, I was once asked to do this thing that was profoundly wrong and immoral, and I didn't do it, but I thought about doing it and I struggled with doing it. And. And the reason that I didn't. I didn't, like, challenge my boss about it was that I didn't want to get fired. Right now, in retrospect, why would I want to keep a job that speaking up about something that was wrong would get you fired from? That's crazy. It doesn't make any sense. But this is. These are the equations that we make in our heads. But why Would you want to work in an administration where even the slightest criticism gets you on the shit list? It's not gonna be a good job. This job that you dreamed of having your whole life, it's not what you think it is, right? Like, they just showed you it's not what you think it is. But we rationalize where everybody. Everybody is saving themselves for this

[Sean Ryan]

higher calling.

[Ryan Holiday]

This higher calling. Yeah, yeah, yeah, I remember. You know, Adam Kinzinger, I remember he was saying he felt like a lot of. I was talking to him once, and he was telling me that he feels like members of Congress tell themselves there's a super Congress, and their job is like, the super Congress will take care of it. And it's like, no, no, you were elected to take care of this. This is what we sent you to Washington. We didn't send you there to be in the job for as long as you could have it. We sent you there to represent our interests and to solve the problems of governance. Right? That's the fucking job. And you think your job is to continue to be congressman or congresswoman, and you're so afraid of being the former senator from Massachusetts or the former congresswoman from California that you aren't making the tough decisions that you have to make. And look, one of the things I've been trying to remind myself of is very easy as citizens to be like, why aren't these people risking their jobs to do what is right? And why aren't they putting themselves out there? And then it's like, you. And by you, I mean the person listening you are working a job you fucking hate. And, you know, you could be doing something different or better. You're working in an industry that, you know is fucked up. Like, blah, blah, blah. What was the last risk you took like that? Like, you know what I mean? It's very easy to evaluate the moral choices and the complicity and the contradictions in other people. And of course, as citizens, it's our job to do that and to throw those people out. That's. You cannot. We cannot keep this republic, as Benjamin Franklin said, if we don't do that. However, to me, the main purpose of looking at this, the cowardice and the contradictions and the shamelessness and the sort of petty turf wars, is it should be a mirror reflected back at ourselves and go, well, I could be doing more. Like, I could be. I tell my kids to follow their dreams, and then I'm, like, not doing it, you know? And so I. I don't know. I just think it's really easy to kind of just point this like judgment lens at Washington or the State House or whatever. But ultimately you got to point it out yourself.

[Sean Ryan]

Yeah, it's interesting you bring that up because I wanted to talk to you about hypocrisy, being a hypocrite. I'm sure we all are. I mean I'm real quick, one of us. Yes, real quick to point it out and everybody else. But I do do a lot of self reflection and I talk to a lot, you know, how can I improve? But I'm always thinking about that, whether it's being a dad, being a businessman, being a podcast, whatever it is, you know, and I can't find the,

[Ryan Holiday]

I

[Sean Ryan]

can't find my own hypocrisy. Does that make sense?

[Ryan Holiday]

On, on.

[Sean Ryan]

I don't know what it is. I don't know. I mean, now I'm sure it'll show up in the comments section.

[Ryan Holiday]

The comments can be helpful for that.

[Sean Ryan]

But, but I don't, I, I can't see it in myself a lot of times. I can't see it in myself. Right. Right now.

[Ryan Holiday]

No, no. I mean, look, this is why, this is why a company's got to have a board of directors. This is why a president is supposed to have a cabinet. I think the most alarming thing about where we are politically right now is that not only are a lot of the governmental checks and balances not there, but a lot of the cultural checks and balances aren't there. Like the press is supposed to be hostile to power and the cabinet is like the founders set up a system where ambition was supposed to be a check against ambition. Right. The Congress was supposed to zealously enforce its prerogatives. Like part of being a senator, like part of the perk of being a senator and having a six year term whereas the President has a four year term is you're supposed to be able to go like this to the President when the President is wrong. Right. Like Congress has war making powers, not the President. But if Congress decides that they don't want to enforce that power, then the President has that power. Right. And you know, if we have a partisan news environment where the left wing media slobbers all over a left wing president and the right wing media slobbers all over the right wing president and then if the President has a cabinet and has been allowed to confirm a cabinet of people who are dependent on him and fully bought in on him, then the President's never going to hear no and never going to hear. That's A dumb fucking idea. What about this? What about that? And so, I mean, we know historically what happens when people in positions of power are not subject to any checks and balances and when their information diet is degraded. Like one of the oldest stories that we have about this is that the Emperor has no clothes, right? And when everyone says, hey sir, we love your new outfit, and he's walking around naked, that there was a. There was a reason, there's a moral to that story. And it's funny actually. Marcus Aurelius, the reason Marcus Aurelius becomes Emperor is actually like 2000 years earlier an illustration of that story. So Hadrian does not have a son. He's the Emperor of Rome. He doesn't have a son, so he has to choose his successor. And there's this kid, he's a member of a sort of prestigious Roman family who somehow he meets. That kid is Marcus Aurelius. And for some reason, Marcus Aurelius as a young kid just doesn't seem to be intimidated by the Emperor at all. And he tells him the truth. And you can imagine that the Emperor of Rome does not hear the truth very often. It's actually a famous story about Hadrian where Hadrian is in an argument with one of his advisors who's a philosopher. And some. It's like, it's. We don't know exactly what it was about, but it was something where it was like, it's like an objective, you know, like anyways, the philosopher ends up saying, you know what, sir, you're right, I was wrong, you're right. And later one of his friends comes up to him and he says, you know, why did you tell the Emperor he was right? Like the math equation is very clear, he's wrong. And the philosopher looks at him and he says, ah, this is what you don't understand. The man who controls 50 legions is always correct, right? Like people don't tell powerful people the truth because they are afraid of powerful people, right? And Marx, Aurelius supposedly tells the Emperor Hadrian the truth, and his nickname is Verismus. Like the truest one. Part of what makes Hadrian ultimately select Marcus Aurelius is that he is like the boy in the story, the Emperor has no clothes, who actually says to the Emperor, sir, you're naked. What are you talking about? Like, I don't care what these people said. You don't have any fucking clothes on. You got conned, right? And so as you become powerful and important and as you. This is why revenge is bad. When you get a reputation for Punishing your enemies or punishing your perceived enemies like critics. It degrades your picture of the world because you have just sent a message to everyone around you. Do not challenge that person. Do not tell them the truth. Do not tell them what they don't want to hear. Do you think there were many advisors who told Putin that invading Ukraine would be a bad idea? Do you think anyone laid out this is how bad it could go?

[Sean Ryan]

No, no.

[Ryan Holiday]

Because you don't want to end up fucking in a plane crash or you don't want to fall out of four story window. And so oftentimes you think you want control, you think you want people on board, you think you want true believers and you don't like the antagonistic, hostile. Like the system of government we have is set up there for a reason. Even the so called deep state is also there for like you want career governmental employees who are not necessarily political. I mean, there can be problems with it too. I don't mean to overstate it, but like you want a bureaucracy that doesn't want to swing too far in one direction or the other direction. You want Congress to be oppositional. You want your cabinet to have their own political ambitions. Lincoln staffs his cabinet with his political rivals because he wants, he knows that what he has to do is extremely difficult. And if he only has people telling him what he wants to hear, he will not actually be able to do it. And so that to me is what alarms me about where we are.

[Sean Ryan]

You brought up an interesting point about where do you draw the line between sending a message, maybe not revenge or vengeance, but sending a message because I've done this where, where I will never initiate. I shouldn't say never. I will not initiate arguments. Blast people, get in fights on the Internet. I just think this shit's stupid and it's a waste of time and causes a lot of stress. But there have been times where powerful people come after me. And then I think it is not just, I think it from, for a variety of reasons, I think it's important to stand up and to engage one, to set an example to anybody else out there that's planning on coming after me. If you do come after me, this is what the fuck's gonna happen. If you back me into a corner. I think it also gives other people courage. I just went through one of these at the, at the beginning of the year, a congressman went after me and I went right back at him. And now he's no longer in Congress. Yeah, but you know, I did that because I I. I mean, I started this in my attic, so I still. I. I don't. I'm still coming to the full realization of the magnitude of the shit that can come out of here, because I still consider myself that guy in the attic that was doing this with my wife. It's a small thing and. But so I'm kind of in the middle of, you know, that makes sense. But I also did that because I wanted to show people, like, you don't have to get pushed around by these people, man. Yeah, they're going to come after you. And it is scary to have somebody that high up in government coming after you, but they don't have as much power as you think they do.

[Ryan Holiday]

Yeah.

[Sean Ryan]

And I just proved that.

[Ryan Holiday]

Yeah.

[Sean Ryan]

And at the same time, I don't want to, you know, for my immediate team, like, I ask anybody that's been here for a little bit, you know, that's. Especially the guys that have been here from the beginning, which is only a handful of them. I'm always asking them, like, hey, what do you think of this? Am I off? Am I off on this? You know, and I think they tell me, you know, especially my top two guys tell me. They tell me, yeah, but, you know, I don't want to. Do you see what I'm getting at?

[Ryan Holiday]

No, totally. Look, sometimes you gotta establish some deterrence or you get. You get pushed around. I think that's important. But yeah, I do think what we're talking about culturally is the problem. Like, we. We want people to stand up. We want people to. To do the right thing. And then what examples do they have of that happening? And I think we're in almost like a cultural death spiral of a lack of those examples. And so I do think it's important. Making a martyr of yourself is usually not a great thing to do, but the idea that there are more people out there that feel this way than people think is really important. Because it's so easy to think, like, oh, everyone's going along with this. Everyone's okay with this. Like, this is just what we have to put up with. And I think it's important. Like, acts of courage, like cowardice is contagious, and so is courage, moral courage and physical courage. Like, if you see someone else do, changes your sense of what's possible and what is sort of the cultural expectation. And I think when I say we're in a desperate. It's like everyone is saving themselves for some crisis. And it's like, dude, this is the crisis that's here, man. How Much worse are you expecting it to get? And look, the Stoics are not exempt from this. As I said, Seneca works for Nero. Now, Seneca probably told himself he was the adult in the room, that he was making Nero less bad and that he prevented Nero from doing a lot of bad stuff. And he almost certainly did. But as a result, he also allowed Nero to do a lot of bad stuff. And these are not easy moral choices. And the only reason, I think, like, 2,000 years later, it becomes a little clearer, right? But in the moment, they are vexing emotional and moral choices. And when you're asking someone to choose, hey, you're going to lose your job over this. You're going to be attacked, maybe your family will be threatened. There's a lot to ask of people. I get that. But chances are, when you look back, you're going to wish you did more. You're going to wish you said more. You're going to wish you're not going to be like, I'm so glad I waited. And because here's the thing about waiting, is that you can always tell yourself that this isn't the right time. That, like, again, no, no, no, no. I need to stay in the room till the real crisis happens. And what you've actually done is over and over and over again built the habit of not doing the thing right. And the idea that suddenly when you're at the second to the top level, that's when you're gonna gamble at all and do the hard thing. You have to build it as a habit. Aristotle said that it was wrong to think of virtue as this thing that you have or don't have. Like that people are born courageous or born generous or simply are smart or any of the things that we hold up as good. He's like, no, no, no. It's a verb, not a noun. It's a thing you are doing or not doing. Like courage is a muscle you are exercising. Like, speaking truth to power is a muscle you are exercising. It's a thing you are doing, not a thing you are or aren't. And so the good news about that is, if you want to be generous, if you want to be a generous person, you can start right now, start tipping bigger, tie the percentage of your salary. You can start doing that right now. That's the good news. The bad news is, if you are not doing it, you are building the habit and the muscle of not being that person. And it becomes harder and harder to break as the stakes get higher and higher.

[Sean Ryan]

That's a damn good Point, Ryan, let's take a quick break. All right.

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[Sean Ryan]

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[Sean Ryan]

Welcome to Hollywood versus reality. They do it right. What does he do in the movies?

[Sponsor/Ad Voice]

Tell me if I'm doing this wrong.

[Sean Ryan]

Cause I don't watch any. A little flick like that.

[Sponsor/Ad Voice]

Right?

[Sean Ryan]

Seems pretty cool. It is pretty cool. Gotta silence it. In another lifetime, I did gun reviews

[Sponsor/Ad Voice]

for a living proprietary magazine.

[Sean Ryan]

Supposedly the best engineering in the world. When that breaks, you're. And now we're bringing him back. It does look pretty cool. I gotta. I gotta admit that. All right, Ryan, we're back from the break. I want to dive into ego.

[Ryan Holiday]

Okay.

[Sean Ryan]

Ego is the enemy. Wrote a whole book on this. Where do we start?

[Ryan Holiday]

I mean, is there anyone that thinks ego is good? Like, is there anyone who's like, we need some bigger egos around here.

[Sean Ryan]

That'll help? I don't think so.

[Ryan Holiday]

I like to think of ego as being the thing that gets between you and whatever it is that you want to do. So in a way, like, I'm not saying, like, oh, be sort of humble. So low to the ground that you don't want anything. You don't try to do anything. Like, I actually think ego is the enemy of the ambition that you have. Like whatever you're trying to do, like what you need is a sense of reality. You need self awareness, you need a sense of connection, you need truth. Like you, the ingredients to doing what you want to do are for the most part not delusion and grandiosity and selfishness. Like it's the opposite of that. So when I say ego is the enemy, I'm not saying like think you're a piece of shit. I'm saying just don't think you're God's gift to humanity. Like confidence to me is somewhere in the middle between those two extremes. And yeah, chances are ego is causing the problems, not solving the problems personally or in your organization.

[Sean Ryan]

How do you keep yours in check? I mean, you're an extremely successful guy.

[Ryan Holiday]

Well, I mean a lot of people

[Sean Ryan]

that find success and then their ego just fucking explodes.

[Ryan Holiday]

Yeah. Look, first and foremost admitting that you have one and that it is a problem is like a critical step. Like if I'm sitting here going like, let me tell you how to conquer your ego, because I don't have one, like be real suspicious because, you know, I mean, my ego causes problems for me all the time. It's something I try to work on. It's something I try to work on and I'd be aware of and knowing that, yeah, like success inflates the ego. Success, it not just inflates the ego, but it enables people around you to inflate the ego in a way. You need to be more self critical and aware the more successful you are. For the reasons we were just talking about, which is the air is thinner and you get less, not only do you get less feedback, but you got this really important piece of feedback that can be really misleading, which is like you did something that wasn't supposed to be possible. You didn't listen to the critics and doubters and haters. And so do you take from that that you know better than everyone else? Right. Like this happens to a lot of entrepreneurs. Like everyone said it was a bad idea, everyone said it didn't work. How do you know when to listen in the future? When Elon Musk started SpaceX, which was his second company, with the money that he made from his first company, his friends had a literal intervention. You cannot do this, this is a bad idea. You will lose everything. It's going to go public and be a multi trillion dollar company. So they were wrong. So how does he now, and by the way, this is also true for Tesla, that was supposedly a bad idea. How does he. I think this is again A sort of larger life story that should help us understand this in our own lives. How does he know in future instances not to just listen to himself? Right. And so he's done some real dumb stuff too. And that's what ego does, is that sense of, I don't need to listen to you, I know better.

[Sean Ryan]

So with that earlier we were chatting about trusting your gut instinct. Obviously Elon trusted his gut instinct when it came to SpaceX. It is wildly successful, maybe the biggest company in the world. Yeah. And you know, and so how do you differentiate what to take in from external influences and what gut instincts to trust?

[Ryan Holiday]

Well, to me it comes down to like the story you tell yourself. Right? So like, like when I went to my publisher and I was like, hey, I want to write a book about stoic philosophy. They were not like Cha Ching, you know, like, they were like, what? You know, that sounds like a horrible idea. Like literally they were like. And I think I said this before, but I took less than half I took for the book that became the obstacles away. I took less than half what I got for Trust me, I'm lying. So they thought it was going to be less than 50% successful as successful. So what's the lesson that I take from that? It ended up selling millions of copies and being this big thing. Do I take from that those fucking idiots at my publisher don't know shit. Do I take from that I'm a genius that I can see around corners, that I know what the people want? Or do I take from this, hey, I had what I thought was a pretty good idea and I could see how it wasn't an obvious home run to some other people. And the reason it succeeded is because of I did the work, I was willing to roll the dice anyway. And also because the downsides of being wrong were not that high either. I took a risk and it paid off. It wasn't a certainty that I knew. It's I took a risk and it paid off. So again, you could take. And we have a thousand examples of this. But like you could take from this, hey, I'm a genius, I know better. That's the ego. Or you can go, hey, I took a risk and it paid off. That's to me, confidence with some self awareness in there. And so whatever story you tell yourself about why you are where you are, it doesn't change what happened. Like the event doesn't know that you're telling a story about it, but it does change how you make future decisions. Right? Like if you feel like you're anointed. If you feel like the rules don't apply, if you feel like you can defy gravity, all these things make it really likely that in the future you're going to overreach. And that tends to be what successful people do, right? They tend to overreach. And so that's what I think you want to take from, from like, trust your gut, but trust the right part about it, not the delusional part of it.

[Sean Ryan]

Do you feel that you have ever overreached?

[Ryan Holiday]

Yeah, I mean, I try to think mostly back around the calls that I made where I was super wrong. Like, I don't think about the fights I had with my publisher where I ended up being right. I think about the times where I insisted on getting my way. And in retrospect, they had a point. You know, I try to think about the, the times where, you know, I didn't listen to the feedback and I would have saved myself a painful bump on the head had I done so. And I think that's healthy. I mean, like, again, if you focus on all the things you know, you don't get any better. If you focus on what you don't know, you can get better. If you focus on where you fell short, you can make improvements. And if you focus on what you got right, you're just jerking yourself off.

[Sean Ryan]

How about humility?

[Ryan Holiday]

I mean, I think humility is important to me. Confidence is, confidence is an awareness of strength and an awareness of weakness. Like, to me, the story of David and Goliath is at its core about the power of both of those things, right. David doesn't think, oh, I'm anointed by God, therefore of course I can defeat Goliath, right? If, if, if he knew that he was preordained to win, he would have just, you know, rushed heedlessly into battle and let God take care of it. Right? Like the story, to me that the, the critical part in the story of David and Goliath is when David tries on the armor of the soldier, his brothers, and it's too big and he goes, I can't do this. Like, this isn't going to work. I'm. He's like as a shepherd, he's just not able to operate as a traditional warrior. And that's when he turns to the sling, right? The sling is, hey, he's bigger than me, he's stronger than me, he's better trained than me. I don't have these tools in my toolkit, but I do have this thing, right? And so humility to me is a key element in matching what every battle, figurative and literal is about, which is about matching strength against weakness. Strength against strength is stupid. It usually creates two losers, even if there's one winner. What a great general does, what a great athlete does, what a great entrepreneur does is match strength against weakness. And by the way, also protects. Hides your own weakness. Right, because that's where you don't want their strength to go against yours. So to me, this humility is really important. Knowing what you're not that good at, what you need to get better at is. Yeah, it's like a big part of it.

[Sean Ryan]

How do you keep yourself humble?

[Ryan Holiday]

You know, the kids help, spouse helps. Trying to do hard shit helps. Like if you are only doing what you're really comfortable with and you're never in situations that you're outmatched, that you're, that you're out of your depth in, you lose that feeling of like, oh, shit, I gotta figure this out. And so like, when I take on projects, one of the things I think about is like, is this something I've done before? And if it's something I've done before, like, it's not that interesting to me. And if it's something where I'm like, oh, I'm gonna have to figure out a lot of different skills to be able to do this. And this can be in. I don't mean like you're reinventing the wheel every time. Like, I just mean, like, what's the element of your game that you're working on? Like, if you go into the off season and you're like, I want to practice getting better at what I'm really good at, I think that that is, you know, not just, not just the gains are going to be less than exciting, but like, it's a sort of a confirmation of ego. But if you're like, hey, no, no. What I'm not good at is this. What I could get better at is this. And that's what you're going to spend your time on. To me, that's that, that helps with humility because you're waking up every day and it's fucking hard. It sucks. And it's just, it's. You can't feel. You can't feel great about how you're doing when you're getting your ass kicked. And so how are you seeking out those experiences? I think that's really important.

[Sean Ryan]

What about with just amongst people? I mean, somebody as successful as yourself, You've reached millions of people with your books, lots of people seek you out. They want to talk to you, they want to meet you, they want to get on an autograph. They want to pick your brain.

[Sponsor/Ad Voice]

They just want to be around.

[Sean Ryan]

And that can really inflate your ego. So how do you navigate that? Especially how do you navigate that around your kids?

[Ryan Holiday]

Yeah. Yeah. It is. Like, when you get recognized around your kids, it's a weird. It's a weird thing. My kids, like, they roll their eyes and they. They. We were in Greece this summer, and they started playing this game where they would. They. They wanted to see if they would see more stray cats than I would get recognized. And the fact that they saw, like, hundreds of more stray cats than I got recognized was, like, a thing they were just constantly shoving in my face, which I love. I loved. And, you know, so, yeah, there is that. I think any. Anything you do in public that has fans or, you know, sort of recognition attached to it can sort of puff you up. I have the benefit in what I do in that it's not mine. I write about an ancient philosophy that has been around for 2500 years. The reason the books work is 90% the philosophy and 10% me. And I try to remind myself of that fact. Like, I am a conduit for a thing that not only did I not invent and can't be credited with, I'm not even good at. Like, my success in writing about stoicism is very different than my individual journey through stoic philosophy as a human being, and I try to remind myself of that.

[Sean Ryan]

Do you consider yourself a stoic?

[Ryan Holiday]

Yeah. I mean, if this is the philosophy that I am interested in, that I am trying to apply in my life, do I call myself a stoic? I mean, I would say I am an aspiring stoic. Like, I would certainly not claim to have attained any kind of enlightenment or mastery of the stuff. Like, in fact, the reason that I'm so driven to write about it and talk about it is because it's like, it's really hard, and I really struggle with it. So I try to remind myself that, like, when someone comes to me and says, like, hey, your books changed my life, they help, you know, or they say, stoicism changed my life. It got me through cancer. Whatever it is, I go, yeah, it worked for me, too. Like, we're on the same journey. Like, what it's. What they think has. Is my books is really, like, the philosophy that I am also a student of, if that makes sense.

[Sean Ryan]

It does make sense.

[Ryan Holiday]

But it's like, you know, when they Interview athletes, like, in the locker room after, like, a big game, and they're like, you know, all glory to God. I think they mean that, and I think that's important. I also think that's, like, a really important professional adaptation. Like, if. If LeBron James or Kobe Bryant or. Or whoever is like, fuck, yeah, that was all fucking me. You know, like, I'm the greatest. That's bad. Like, that's bad for future performance. It's better. It's better to credit. And I don't just mean, like, from a public relations standpoint. Like, you have to mean it. Like, if it's false modesty, it's a pro. It's. You might as well just own it. But if you're like, no, this was the team. This was the training. This is the tradition, That is the right and the healthy way to think about it. First off, because it's true. And second, because it's not good for you to put that on and credit yourself for things that.

[Sean Ryan]

Why is it not good?

[Ryan Holiday]

Well, I think, as I said, first off, it's not good because it's not true. Right. Like, everything is a team sport. Right. And second, because it breeds complacency and entitlement. And if it's not a little scary to you and it's not a little hard and you're not questioning your ability to do it, you're probably going in the opposite direction. Like, you're, You're. You're. It should be getting. It should always stay challenging and hard. Or. Or else it's like, you know, you're lifting weights. When it becomes easy, you grew. You grew the muscles, and you. You need to crank the thing up.

[Sean Ryan]

Makes sense. Let's move into. How do I word this? People that have experienced death or been close to death or I guess not experienced death, but they've been around death. People that have killed, people that have seen war, people that have been around death a lot and kind of knowing when to act, when to let things go, that kind of stuff. I mean, you have a lot to say on that.

[Ryan Holiday]

I mean, I'd be. I'd be curious your opinion. I mean, when. When you experience how fragile life is, does it turn down the volume on stuff for you for a little bit? Yeah. Then it creeps back.

[Sean Ryan]

And then it creeps back.

[Ryan Holiday]

Yeah.

[Sean Ryan]

I liked everything I was reading, and then I did. I compared it to myself, and I was like, you know, a lot of this stuff bleeds back.

[Ryan Holiday]

Yeah.

[Sean Ryan]

And then. And then you get, you know, in my life journey, in my previous Life, it was, you know, there was constant. You're humbled again, you're humbled again, you're humbled again. Somebody died, somebody died, we killed somebody. Somebody, you know, and so there's that constant reminder. And you live in that pretty regularly. Then I left, and I'm not around it anymore. And things that maybe don't matter or shouldn't matter, they creep back in and they seem like a bigger deal than they are. And then I go into my revenge planning, or you know what I mean? And I'm just being honest. It fucking creeps back in. And it creeps back in faster than you would think.

[Ryan Holiday]

Yeah. A friend of mine is in martial arts, was telling me that it's like sweeping the floor. You don't sweep it once and it's clean forever. It's a constant process of sweeping. And I think ego's that way. And I think, like, the urgency of life is another one. Like, you go to the doctor and they're like, oh, I need to check that out. There's that moment where you're like, oh, shit, is this it? You know, did it just get serious? Or, you know, you were talking to a friend on Friday, and then you find out over the weekend they died, or, you know, natural disaster, you know, whatever, Anything that happens. And suddenly you're like, oh, I forgot, we're mortal. The Stoic practice is memento mori. Like, remember, you are mortal. But it has to be an active meditation because, like, we all know objectively that we're all going to die. Like, every person who's ever lived has eventually died. There's no way out alive. And we know that. Although, on average, this is about how long we have, people die before they should all the time. The healthiest people in the world drop dead of a heart attack. The greatest people in the world get murdered for the money in their wallet. Obviously wars and natural disasters, it happens. But then you get a little soft, a little entitled. You drift away from that urgency. And so, yeah, to me, it's an active process of reminding yourself that, yeah, tomorrow is not certain, the future is not yours. One of the, I think, the most powerful ideas from the Stoics, this comes from Seneca, you know. He says it's wrong to think of death as something that happens in the future. Like, that death is something we're moving towards. He says, actually death is behind us. He says, like, the time that passes belongs to death. So instead of thinking like, you live 80 years, he says, like, you've died however many years you're currently Old. So, like, I'm gonna. I turn 38 next. 38. No, 39 next month. I don't remember. But anyways, like, my birthday, I should look back and go, this is how many years I have died. What do I have to show for that? Not how many years do I have left, but what do I have to show for the time? Because how we spend our time is how we spend our life, Right? And so the idea of going, like, hey, oh, I don't like this, but I'm going to do it until my kids grow up. Or I'm going to do it, you know, for a couple more years. I'm going to do it till things settle down. Like, you know, we. We tell ourselves, like, we make these assumptions about the future, and really, the only thing that's certain is. Is now the thing you're. You're paying for with your life right now. And so that I do try to remind myself of that. That, like, we don't. The choices we're making about our time right now are the choices that matter. The idea of working something you don't like, deferring something you don't like, because what you really want to do is play golf in your 70s is naive and entitled. And so, by the way, is just the basic procrastination of, like, you know what? I think I'm going to start that project next week. If you're going to do it, you should do it and you should start right now. That, to me, is the. What you take out of the momentum where you practice.

[Sean Ryan]

Yeah. I really struggle with this. And just in my personal experience, every time that I have been around death, thought I was gonna die. There's only one thing that goes through your mind, and that is. That's your family. That's it. That's the. It's not all your shit.

[Ryan Holiday]

Yeah.

[Sean Ryan]

It's not all your accomplishments. It's not what you've done at work. It's not any of that. It's not how much money. The only thing is, like, you know, who's gonna watch out for my family.

[Ryan Holiday]

Yeah.

[Sean Ryan]

When I'm out of here. And. And then, you know, that. That creates the fight, you know, to stay alive.

[Sponsor/Ad Voice]

But what you're.

[Sean Ryan]

What you're talking about, I. And I still struggle with this. No matter how many times I thought I was gonna die or been around it or been close to it, I've had that constant reminder like, none of this shit matters. The only thing that matters in my head is my family. But then there's the Preparation. I have to hit this financial benchmark. I have to hit this. I have to hit all these accomplishments or goals or whatever it may be to make the future of my life, my wife's life, my kids life, hopefully

[Sponsor/Ad Voice]

easier in the future, which takes away

[Sean Ryan]

from living in the now because it's all planning, right?

[Ryan Holiday]

Well, even more insidious. Like at some point you would give literally all of it back for five more minutes of time with them, right? And then here you are fucking doom scrolling on Twitter with the five minutes that you have for sure right now. Like you're going to look back and wish that you could have more of this. And what are you doing with it right now? You're wasting it. And that to me is what I take from it is like I have the thing that in the future will be priceless and unattainable and I'm so frivolous with it. And I say yes to things because I don't want to be rude to someone. I get distracted because something's happening in the world. I, you know, I get overwhelmed and I'm like, I'm going to take a break, you know, like. And you experience it in little, like already. Like if you have little kids, you're just like, dude, like a year ago, like that's gone, right? Like these periods are so fleeting and so short and in the moment you want like the next thing you want to get out of it. I can't wait till they walk, I can't wait till they talk, I can't wait till they drive, whatever it is. And then actually when those moments come, all you wish for is more of what you wished away in the moment because you're entitled or short tempered or frustrated or whatever.

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[Sean Ryan]

How do you reset? Do you find yourself going down those rabbit holes, too?

[Ryan Holiday]

Yeah, of course. I mean, I. I try. I try to. The good news about the present moment is that you're always getting another one until the moment that you don't. And so how. To me, how quickly can you get like, shit, I'm throwing the phone down. Like, I'm stopping right now. Not like, tomorrow, I'll do better, but like, I'm stopping right now. It's like, how fast can you get back to center? Is to me, like, the key. The key skill, both as a parent and as a person in this crazy modern world. But, you know, today was rough. Okay, how do you do better tomorrow? And how do you stop. Whatever the direction you're going in that you know you shouldn't be going in and how quickly you can do that?

[Sean Ryan]

What are your indications? Do they come from you? Do they come from your wife, your kids?

[Ryan Holiday]

Yeah. I mean, I feel like parenting is a lot of. After they go to bed, you're like, man, what are we doing? Why did it go this way? You know, it's that sort of debrief at night. To me, that's. That's. You know, and it's very rarely, man, we crushed it today. Like, it's usually like, why did we try to squeeze one more thing in? You know, why did. Why. Why did. Why did I. I remember I was putting my son down for bed the other night, and, you know, first off, can I have a little more iPad time? Then I got to brush my teeth. Oh, no, now I got to go to the bathroom again. Or, oh, no, now I need water. Oh, I'm hungry, even though I had dinner twice. You know, all this stuff that he's making up for, you know, not going to bed. And then I finally. He's like, all right. We go in his room. And I'm like, all right, let's get in bed. And he's like, no, no, I'm sleeping on the floor. And I go, what? You're not sleeping on the floor? Like, and then we just got in this huge. You know, it's like, what do you mean? You never said I couldn't sleep on the floor. We get this whole fucking argument about why couldn't sleep on the floor. And then I was finally, like. I was like, why do I have an opinion about this? You know, like, sleep on the floor, I don't care. I realized, like, I think in the moment, it was like, I didn't want him to sleep on the floor because here's what I knew what happened. He would sleep on the floor until, like, the middle of the night and then wake up, and then he'd come in our room, you know? And I was like, I wanted sleep, right? Like, I was extrapolating what this means, what, you know, like, instead of going like, I don't care where you fall asleep, I was thinking about what it means if you sleep here or there, right? And so anyways, finally, I'm like. I realized I'd gotten down. I was in a battle of wills that I had the power to end right then by saying, sleep wherever you want. If you want to sleep on this teddy bear on the floor, knock yourself out. So anyways, he lays down, and just when I think he's fallen asleep and I go to leave, he goes, I'm ready to sleep in my bed now. And I go, all right, let's go. And he walks in and he falls asleep in his bed. And it was such an illustrative one for me because it's like, I know when it started. It started when we walked into his room and he said I wanted to sleep on the floor, and I said no. And then it ended with him realizing that he didn't want to sleep on the floor and he would rather sleep in his bed. And that whole argument, you know, where I argued one thing, and then I realized I was wrong, and then I changed. Like, that whole thing in the middle, it just didn't fucking need to happen, you know? Like, the whole, like, it. It would have worked itself out had I been a little more go with the flow about something. And I think what I took from that, as a parent is just like, I need to be more in the. Like, does this thing actually matter? Like, why am I thinking that this matters? And I'm thinking that it matters because I'm thinking about what it means as opposed to. That it means nothing, right? And that I could save us both a lot. Like, I could save us both a lot of trouble. And in fact, not only did it work itself out, but it worked itself out. Except we also had a big argument in the middle which has a cost to it. Right. And so look, I'm not saying you do everything your kids want and you let you know you got king baby walking around. But most of the conflict, like when I think about the things I had conflict with, with my parents, how many of those in retrospect were significant in any way, you know, and how many of those things are they glad that they went to the mattresses on? And I'm trying to get better at that.

[Sean Ryan]

You're saying pick your battles.

[Ryan Holiday]

Totally. And, and, and by pick your battles, I mean avoid 99.9 of the battles because they don't matter.

[Sean Ryan]

So how do you guide of that? I mean, now we're moving into fatherhood, so. Yeah, how do you. I'm just curious, how do you guide them without confrontation, without discipline, disciplining them?

[Ryan Holiday]

Yeah, I mean, yeah, of course that's the challenge is like you're not creating this fantasy world where they get to do whatever they want, whenever they want it, but at the same time, like again, why do I care whether you sleep on the floor or their bed? There's no lesson in here. What there actually is is me wondering about the consequences of this for me. And two, my desire for control. Right. Like you want to do this and I want you to do this and why am I going to let a six year old win? You know, so in a way you think like, oh, I'm giving them discipline, I'm giving them structure. It's very helpful actually. You're just showing them like authority is arbitrary and pointless and should be fought against every. Like you're actually sending the exact opposite lesson you want. And again, I'm saying this all as someone who constantly struggles with this. So I'm not saying this is something I'm good at. It's precisely the opposite. But I mean, look, you teach your kids by example and you teach your kids often in the moments when they are open to being taught because they've experienced some kind of consequence or

[Sean Ryan]

for

[Ryan Holiday]

a choice or there is an opening because of something that's happened, for you to actually insert that thing, that bit of wisdom or experience or lesson or whatever. That's kind of how I think about it.

[Sean Ryan]

Okay. I mean, you wrote a whole book on stoic fatherhood, correct?

[Ryan Holiday]

Well, I did a book, I did a book called the Daily dad, which is just sort of classical or ancient lessons, like one a day. I think the problem with parenting books is like you're supposed to read this book and then just be good. I'm supposed to read about when my kid is 13 months, I'm reading about how you teach things to a 13 year old. Like I'm not going to remember any of this. So the idea of the Daily dad is. It's an email too. The Daily dad email is just one thought a day. I think to me parenting is like a series of values and lessons that you've got to be reminded of over and over and over again. And that's kind of what I've tried to do with it.

[Sean Ryan]

What are some of the most important ones that stick out to you?

[Ryan Holiday]

Yeah, I think that the most important one I think is just how fast this is all going and that you. Every time I cut my kids fingernails or take them to get a haircut, I go like, that's that much life right there. That's that much of the brief window that they live in my house, right. That we get to do things together. And I try to be always aware. Just as memento mori is about your own mortality. Realizing that I don't have a 2 year old anymore, my 3 year old is dead and gone, my 4 year old is dead and gone. You are cycling through those ages and they will never be that thing again. To me that's like one of the ultimate parenting lessons. The other one my wife and I were related to that was like, we were like, do we want to. There was like some kids concert or something. We were thinking about going and we're like, but we got to get in the car. It's like a 30 minute drive. Are they going to appreciate it? And it was just like, how many more times are they going to want to do this? You know, probably not that many more. Like at some point there's the last time and are we going to be glad that we stayed at home and didn't do the thing or are we going to be glad that we did the thing? So realizing that you only get so many shots of these things, I think is a big one that you are the voice that's going to be in their head. And what is that voice like? Is it a negative voice, is it a positive voice? Bruce Springsteen talked about how we're going to be either ancestors or ghosts to our children. Like an ancestor guides and a ghost haunts. And what, what kind of example are you going to?

[Sean Ryan]

I never thought of it like that.

[Ryan Holiday]

And it's not just like what you say, but also like, is dad working on his shit, his mom working on her shit? Or are they just foisting that stuff on you? And so like thinking about Getting serious about the stuff that, you know, you need to address, you know, you need to work on. I think that's one. And then related to that, I think, like, I have. I've never lost my temper at my kids, and then afterward, been like, I'm so glad I did that.

[Sean Ryan]

Yeah.

[Ryan Holiday]

One I have, like, on my phone, you know, it cycles through, like, pictures of my kids, like, as my home screen. And one of the things I'm always struck by is, like, how little they were. Like, I was real fucking pissed. At a very small person. It doesn't age well. The things you get upset about, the things that you thought were a big deal. As they get older and you get a little better at this parenting thing, I think that the disparity of them and you becomes more obvious. And I'm like, why did I. Like, like. Like, what do I give a shit about the backseat of the car so much for, you know. Or, like, you know, you walk in and he's drawn on the wall or, you know, broke something. You know, where's. Where's the car that my parents were really concerned about me spilling my McDonald's ketchup on? Like, it's in a. It's in a fucking cube somewhere.

[Sean Ryan]

Yeah.

[Ryan Holiday]

Like, it doesn't. Like, it did not ultimately affect the resale value of said car. It did not teach me any lessons about cleanliness. Like, it. It was just like, a stupid argument that we had. Right. Like, and I try to think about that. Again, not good at it. But I try to go, like, where will this thing be in the future? Am I going to care about it?

[Sean Ryan]

You don't put importance on any things.

[Ryan Holiday]

Yeah. Or I try to get better at. Not the human or the thing. What do I care more about? The marriage advice is like, do you want to be right? You want to be married? You know, do you. Do you want to have a good relationship with your kids, or do you want to get your way all the time?

[Sean Ryan]

How do you know if you're. I mean, this is a really good way to put it. If you're a positive or a negative in your. In your kid's mind, how do you gauge that?

[Ryan Holiday]

To me, I think. It comes down to. No parent is perfect. Every therapy session ultimately ends up in all the ways that your parents could have done better or whatever. But people say, oh, my parents did the best they could. I'm not sure that's always true. And so are you actually doing your best? To me, the question is, like, I go, you know, I'm doing my Best. And I go, am I. Because I feel like I try a lot harder at other stuff. Like, I'm not saying parenting is easy, but I feel like I do a lot more work evaluating myself professionally. I bring in a lot more help professionally. I measure myself better professionally. And then a lot of times as a parent, I'm just winging it. And then. And then I wanna. I want them to let me off the hook and go, dad was doing his best. Like, I'm not sure that's true. And so that. That does kind of push me to try to do better.

[Sean Ryan]

Damn. It's like, me, I'm like that.

[Ryan Holiday]

Yeah. Because, look, and I think culturally, for. For men especially, right? Like, your job was where you were supposed to be your best, where you prove yourself. And then parenting was like an afterthought, and the expectations were, you know, that expression, the soft bigotry of low expectations. That's basically dudes for all of human history when it comes to parenting. And, like, I don't know. I. I want. I want to do better than that.

[Sean Ryan]

What are the. I mean, what are the steps that you're taking that you're thinking about taking? That. That. That. That create a better balance?

[Ryan Holiday]

Yeah. I mean, I. To me, a big one is like, okay, so you're really good at what you do. You're successful at it. And then. And then you think that that somehow, like, exempts you from having to do shit at home, right? Like, like, obviously, look, managing your time and delegating where you can, but you're like, why am I assuming that, like, my wife should make the school lunches? Or there's this. They did this interesting study of, like, schools where, like, they needed something at home. Like. Like, there's some problem at the school, right? And the. The.

[Sean Ryan]

The.

[Ryan Holiday]

The receptionist or the principal or whatever had to call the parent. Like, what percentage of the time do they call the dad?

[Sean Ryan]

Probably a very small percentage.

[Ryan Holiday]

And there. There's. There's the assumption of the person making the call, and then there's also the reality of, like, the family. Like, and, like, I've worked really hard, and my wife and I, like, whenever we hire, like, an assistant or we're like. We're like, there's no. We're both the default parent. Like, it's not, like, call her if there's anything important, and then call Ryan if you can't reach her. You know, like, I want to make this a thing that I value and that. I heard someone say, your kids are not a distraction from your work. They are your work. And that's easy to say, but what does your calendar say? What does your division of household labor say? Like, your kid has a birthday. Are you just showing up at the birthday party, or did you make planning decisions? You know, did you make purchase decisions? Did you. Did it catch you off guard that it was. There's just. There's just an assumption. I think it's. Look, it's obviously better than it's ever been before, but there is, like, an assumption that, like, that's not, like, the term for. This is emotional labor. That's not emotional labor that the father should have to do unless they're, like, a single parent or, you know, whatever. And I'm not saying it came easy, and I'm not saying it came voluntarily. I'm just saying, like, in my marriage and in my family, my wife and I have tried to not do that. And it's been like I've had to learn how to do a bunch of things that I would not. I would not normally be inclined to do or be good at. I've had to figure out how to do.

[Sean Ryan]

Man. It's. It's just a. Man. It's such a dichotomy. Right. I mean, I think about this all the time. I've talked about this several times on the show. I mean, my wife and I have, like, this little bitty hunt cabin that's. It is, like. Looks like you could blow on it, fall over.

[Ryan Holiday]

Yeah.

[Sean Ryan]

You know, it's. It's. It's all one room. You know, the kitchen, the bathroom. It's all one room.

[Ryan Holiday]

Yeah.

[Sean Ryan]

And.

[Ryan Holiday]

And.

[Sean Ryan]

And before my kids were born, we would spend weekends down there and just to. We live out in the women East.

[Ryan Holiday]

Yeah.

[Sean Ryan]

We live out in the woods. You go down there, you're really out in the woods, and that's the. Some of the happiest times I've had with my wife is down there. Zero. There's no cell reception. There's no Internet. There's nothing. And. I keep coming back to this, which I love doing this, but I'm happier right there. No distractions. I'm in the moment.

[Ryan Holiday]

Sure.

[Sean Ryan]

And, you know, and now that I'm close to being able to just. I could do that. I could get rid. I could sell.

[Ryan Holiday]

Sure.

[Sean Ryan]

The studio I could do. I could get rid of all of this. Sell it. It'd be totally fine financially and actually live that life where I'm 100% dedicated to my family.

[Ryan Holiday]

Yeah.

[Sean Ryan]

100% of the time.

[Ryan Holiday]

Yeah.

[Sean Ryan]

And knowing that I would probably be happier yeah, I. 99% sure I would be a happier person, you know, if I. If I put all the. Even though I love doing this, you know, put all the world's distractions into it, just away from my life, but I still fucking come back to this.

[Ryan Holiday]

Yeah.

[Sean Ryan]

Because I love it. And I also think about, you know, well, what would it be better? Would it. Realistically, would it be better for me to be there 100% of the time for my.

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For my wife and my two kids?

[Sean Ryan]

And what kind of example is that setting for my son? Because that's not how society is set up.

[Ryan Holiday]

Yeah. It's an interesting question. Is it better for them? Is it.

[Sean Ryan]

It's better for them right now. Is it better for their future?

[Ryan Holiday]

Yeah.

[Sean Ryan]

Because they're going to hit a point where they're going to have to provide for their family. It's unattractive. I personally think it's unattractive for a woman to whether. Whether he is a wealthy, financially wealthy man or not a trust fund baby. You know, I don't think. I don't think women. I don't think that's a real attraction.

[Ryan Holiday]

Sure.

[Sean Ryan]

You know.

[Ryan Holiday]

Yeah.

[Sean Ryan]

To find in a.

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[Ryan Holiday]

Sure.

[Sean Ryan]

You know, and so if he doesn't. If he doesn't see me providing for the family and doing things that in my opinion, men should be doing as the. As the leader of the household, then what happens to him when he comes of age to find a wife and have kids and provide?

[Ryan Holiday]

Well, don't you also think of that

[Sean Ryan]

example then what is that gonna lead to? And he may not ever find somebody if he doesn't get that example.

[Ryan Holiday]

I remember a couple weeks into the pandemic, my wife was like, please never be home this much ever again. And obviously I had to do some work on being like, okay, I have to become a more stable, chill person, because this is currently operating in a way that's only good in small doses. Right. That wasn't good. At the same time, to take the energy and the drives and the competence and the mastery, all the stuff that you have, and be like, I'm gonna put all this at home. You know, I think that's also how you get stage parents and, you know, sports parents. Like, what are stage parents? I just mean, like the parents that make all facets of their existence, their family. Right. And then all of a sudden, you're just channeling that energy. Yeah. At home, like, it's. There's an intensity and a. And an energy that has to have a release valve. And I think Work and impact, like, that shouldn't all be on your family. We're meant to go out and do things and to figure things out. And it's like, so you're just gonna drive him to school and then play golf all day? Like, I'm not sure that's, that's not thriving as a human being either, or setting a good example either. So there's a tension. But yeah, I think one of the things that bothers me and I think we all delude ourselves with it, is we go, like, I do this all for my family. It's like, no, you don't. You stop needing to do this for your family a long time ago. This is about you. Right. And, and that's not to say it's not about them at all, but like, you're a billionaire, dude. Like, you're not doing this for anybody. You're doing this because there's never enough for you. And so it can be very easy to take something selfish and make it seem like it's selfless.

[Sean Ryan]

Justify it.

[Ryan Holiday]

Yeah. And so understanding the tension between those two things and like what I've tried, I've tried to say and work on a way that I can be really good at what I do and keep it within some reasonable hours. Boundaries and systems to me, what I'm working on, I'm not trying to sell the most books in the world, have the most impact in the world or be the most famous or any. I'm trying to be really good at what I do and be a really good parent. And that in a way, that's actually a more difficult needle to thread than just being all in one or all in the other. And I think it's important that we understand that that's possible to do. Like the athletes that I admire or the entrepreneurs that I admire or the leaders that I admire are not the maniacs. Right. It's the ones who seem to be reasonably well adjusted human beings also. Right. Like sometimes you read about these, like, this is my daily routine. This is my system. This is how so and so prepares in the off season. And you're like, well, I'm sure that's all really easy to do if you don't fucking see your family. You know, like, if you're a piece of shit, that's easier. Yeah, it's, it's. Can you, can you be in great shape? Can you do what you do? Can you perform at a high level and do school drop off or, I don't know, be involved and be, be present when you're you know, like, can, can you. Like, that's the challenge for me. Like it used to be like when I was working on a book, I was just an all consuming thing. I don't just mean the hours, I just mean like, I couldn't turn it off. And now I try to judge the success on a book on like how, how, how not disruptive it is.

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[Sean Ryan]

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[Sean Ryan]

Not overly tactical, just modern functional design that works every day.

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[Sean Ryan]

code SRS how do you, I mean, what are your indicators for you that tell you if you're leaning.

[Ryan Holiday]

Yeah.

[Sean Ryan]

Talking to you? I doubt you lean too far into family. It seems like you probably leaned too far into work.

[Ryan Holiday]

Yes.

[Sean Ryan]

You know, and so what are, what are your indicators? That's that let you know. Is it a personal guilt? Is it a, is it the way your kids are acting or communicating to you? Is it your wife? What is, what is, what are your indicators?

[Ryan Holiday]

Yeah, I mean, look, just practically, I try to measure like the stuff that I do or I say yes to. I measure it in bedtimes. Like how many bedtimes I'm going to miss for this thing. And like one is a lot, two is usually too many. Right. So I try to, I try to measure it in bedtimes. So that's like, that's kind of my North Star. Like how physically is this taking me away? Yes or no? And that's kind of how I judge the stuff that comes my way. That being said, that can be a way of fooling yourself, which is like, you're there, but you're not really there. So I try to think about, like, hey, how is my emotional state, my focus, like, am I the reason that this is all dysregulated or am I the calming presence? Right? And I think too often, like, I'm, it's like I came home amped, I came home worked up, I'm stressed, I'm distracted. And you can, like, I think you can just feel the energy in the family dynamic. And I want to be the solution, not the problem. And I think I know I'm not taking care of the things I need to be taken care of, and I'm not doing what I'm supposed to be doing when I am. I'm the problem. You know, like, if the three year old is upset because they're a three year old, great. If the three year old is upset because you snapped at them because you were trying to play with them and check your phone at the same time, you're the problem. And so I try to think about that, like, how am I fitting into this system, this sort of wavelength, as opposed to, I want to make it all about me.

[Sean Ryan]

Makes a lot of sense. Makes a lot of sense.

[Ryan Holiday]

And then you should have a, a spouse and a family dynamic, co, parent, whatever it is for you, where they're like, dude, what was that? You know, like, like, I think my wife and I talk a lot about, like, like, let's back each other up in the moment. You know, let's not throw each other under the bus in front of the kids. But like, afterwards, like, yo, you can't do that. Like, you know, you can't do that. You saw, you saw when you made that choice, right? It goes both directions. But like, I think if, if, if, if you're not making each other better as parents, you're not, you're not doing your job.

[Sean Ryan]

Yeah, yeah. You know Steve Ranella's book.

[Ryan Holiday]

Yeah.

[Sean Ryan]

About outdoor kids and then Inside World. I mean, there's so many studies that talk about, you know, the more kids are outside the, I mean, the percentage of them having depression decreases dramatically. I mean, less screen time, depression decreases dramatically. You raising your kids on a farm. Correct.

[Ryan Holiday]

My son's, my youngest, is in first grade, and when he started in August, it was the first time he ever sat at a desk because he went, he did kindergarten and pre K for several years at an outdoor school. Like, they would go, there was no buildings, and they did it outside, rain or shine. You know, they ate their lunch around a campfire and they did all the stuff outside.

[Sean Ryan]

That's awesome.

[Ryan Holiday]

And it was incredible.

[Sean Ryan]

What's that kind of education called?

[Ryan Holiday]

I think it's just called. It's like a nature school or an outdoor school. I guarantee you there's one around here. And it was incredible. And, you know, that was a big choice for us. And then, you know, we, like, one of our big things is like, okay, sure, screens are maybe better parents than us could exist in a screen free household. That ship has sailed. But, like, we try to use them to, like, how is that an entry point into a world that we. We are by nature of where we are financially and the freedom we have. Like, we. I can show you that world, right? Like, my. My boys got really into this podcast called Greeking out, which is. It's all about the Greek myths. It's amazing. It's like 10 seasons. They listen to every episode multiple times. And so, like, we went on a road trip across Greece, going to Rome this year. Like, you get. If they get interested in a thing because they watch a video about it, they hear about it, like, let's go experience that thing in real life. So to me, like, one of the most important skills you can have in life is first curiosity, but then second, the ability to take that curiosity to its natural conclusion, right? Like, if you're interested in something or you don't know about something, do you have the skills to go figure it out? You know, like, there are books about that, there are videos about that, there are podcasts about that. There are places we can go, there are experts about this thing. There's AI, Right? Like, how you. To me, I try to see the screen as an entry point into the enormity of the world. And then it's like the algorithm is exposing themselves to stuff. And then because they're interested in it, my job as a parent is to take them down that rabbit hole.

[Sean Ryan]

Okay.

[Ryan Holiday]

And so that's kind of how we think about learning and doing stuff.

[Sean Ryan]

I like that.

[Ryan Holiday]

Like, oh, we're going on this road trip now, I guess. Or. And I'm showing them stuff, right? It's like I showed my son this Saturday Night Live video, and he thought it was hilarious. And then it's like, oh, you want to take an improv class now? Done. Or, oh, did you actually know Lorne Michael's papers are at a museum in Austin? Let's go do that. So that idea of they have that flicker of interest or awareness of something. How do you take them down that rabbit hole?

[Sean Ryan]

So they show interest and you immediately act on it.

[Ryan Holiday]

Yeah, yeah. And like, it's not heavy handed, but it's like, oh, there's so much more of that you don't even know. And that's like. That gets me excited. Right. Because, like, sometimes it's something I know a lot about and I get to show you all the things that I know about it and that I love about it. And then sometimes it's something I know nothing about and we get to go learn about that together.

[Sean Ryan]

Do you introduce things to all of them as well?

[Ryan Holiday]

Yeah, yeah. It's like, you're always like, what about this? What about that? And, you know, you don't have a great hit rate, but when it lights them up, that's like the best. Like music, movies. Yeah.

[Sean Ryan]

Nice. Let's talk. I'm dying to talk about this.

[Ryan Holiday]

All right, Churchill.

[Sean Ryan]

Yeah.

[Ryan Holiday]

Okay.

[Sean Ryan]

I didn't grow up with money.

[Ryan Holiday]

Yeah.

[Sean Ryan]

Was never around it, you know. And now I find myself making a pretty decent amount.

[Ryan Holiday]

Yeah. And.

[Sean Ryan]

I don't know where to look to, you know, how do you raise kids with that? Keep them humble, keep them from being entitled, keep them from idolizing shit.

[Ryan Holiday]

Yeah.

[Sean Ryan]

Fucking cars, watches, whatever. You know that.

[Ryan Holiday]

Yeah.

[Sean Ryan]

Luxury items or, you know, how do you do it?

[Ryan Holiday]

I don't know. And you don't know whether you see

[Sean Ryan]

all these people that have grown up with it. And a lot of times I don't like the way they turn out. You know, I don't wish that for my kids. I'll say that.

[Ryan Holiday]

And you don't know if you're doing a good job until it's like, too late. Yeah. No, I think. I think it's the thing that keeps parents up at night. I remember I was talking to Matthew McConaughey one time and he said, you know, there were a lot of things when he was a kid where it was like, we can't. But then you find yourself in a position as a parent that's very different. And it's like, we're not going to, like, we don't do that. In a way, it's not easier because it's hard to not have enough, but it takes the choice out of things. Right. Like, yeah. You know, and I think, I think not to idealize the past, but like, there used to be society was the, the, the. The income inequality was less. Like, we've never existed with this level of income inequality in this sort of stratified. World where it's like, okay, now, it used to be there was first class and economy on an airplane. Now not only are these different levels on an airplane, but there's private. And the people who are flying private are living in a very different world than the people who are not. And how do you, how do you stay in reality? I think is like the first, the first challenge. Especially as, you know, people get to levels where, you know, it's, it's inconsequential to them, like what this costs or that costs. You. You have to create some artificial boundaries and rules, I think. I just, I don't know.

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[Sean Ryan]

It is because they have to like, you could starve them from all of that as a parent and you can, you can start, but then on the other hand, eventually they're going to be in it. And if they don't know how to act and when they're around it, then I also think you're doing them a disservice. And so they really need to know how to operate in both worlds, in my opinion. How do you get them to operate in both worlds without becoming a self entitled, selfish piece of shit? I mean, for lack of a better

[Ryan Holiday]

word, look, it's a timeless challenge. Plutarch, one of the great biographers of antiquity, was talking about how parents will spend a lot of time on their will trying to create an estate. Who's going to manage the estate? Who's going to be the guardians? How much money do they get? Spent a lot of time thinking about that and not enough time thinking about, how do I raise a person with enough character that they can handle it instead of being like, oh, we're creating a trust fund. And the trust fund gives them this much per year, which is just enough and not too many. It's like, you could also just spend your time trying to raise a child who has good values and a good work ethic and doesn't derive their value from luxury goods. Right. So I think it's a challenge. Certainly, again, nothing close to the challenge of being a single mother on food stamps, trying to raise three kids or whatever. But it comes with its own challenges and ultimately I think we have to model it and then I think we have to. Like, the most valuable gift you can give your kid is not, you know, a huge estate. It's like the ability to. Have the thing that lights them up that they like doing that they want to spend their life doing. Robert Green, my mentor, he calls this your life's task. What is Your life's task, what were you put here to do? And I think our job as parents is to help our kids find that thing, to create an environment where they can find that thing and be supported and loved in pursuing that thing. You know, it's not to make them a doctor or a lawyer or to inherit the family business. It's to find the thing that if they didn't do, not only would they be unhappy, but the world would be worse off for them not doing it. I mean.

[Sean Ryan]

But I want to say something too, just for the audience. I mean, I don't want to sound like a couple of fucking elitists, you know, sitting up here talking about this, but this is because we're not even talking about what we have, what we don't have. We're just anybody who finds himself in a position that they are doing better than their parents did. This applies to them, whether. You know what I mean?

[Ryan Holiday]

Look, your average American has a level of choice and privilege that a struggling family almost anywhere else in the world is not having to think about that. So this is privilege, but in a way that we're all privileged and there's just different degrees of it. But yeah, how do you raise a kid who is resilient, who is in like stoicism to me is about being in control of yourself, being master of yourself. And that's what we're trying. Like you're trying to raise kids who can go through life and are not going to be, as we said, don't say ew a lot, don't throw in the towel a lot, don't expect other people to solve their problems for them. How do you raise self sufficient, resilient kids? That's the challenge of our time. And yet it's also the most timeless challenge for us. Every parent for all time has had to deal with that in some form or another. And I think, I don't think there's one thing you do. I think it's a handful of things.

[Sean Ryan]

Do you think it's how you act? The things that I've learned and my kids are very young. My oldest is close to five. But, you know, I think it is. I really am starting to think it's the only thing that really matters is the example that you set for them.

[Ryan Holiday]

Yeah.

[Sean Ryan]

So if you idolize your shit, they're going to idolize their shit. If you get pissed because they fucking scratch your car, break a window, whatever, break a vase, anything, you know, and you, you overreact and idolize the thing that's going to be passed on. Yeah, Same with people. You know, they're going to look to see how you treat people. All people.

[Ryan Holiday]

Yeah.

[Sean Ryan]

Not people you look up to and people that you think that you're above all people. And they're going to take that in. And hopefully the financial aspect, it doesn't have any relevance if you lead by example.

[Ryan Holiday]

Yeah. They say your kids don't always listen, but they're always watching. And a way to think about it is, let's say you never gave them a single piece of advice. Like, you never told your kids, do this, don't do that. This is important. That's not important. This is what we believe. These are our values. What do you think they would deduce about what you think about those things from the life that you lead? If you were tried in court, would you be convicted of those beliefs from your actions? I think that's like, you know, I think about this. It's like, okay, so I write about stoicism, but if, If I didn't, would my kids say that that's what I believe in or care about? That would that be how they would describe me? You know, and that, that, like, that's the message that ultimately matters. Like, what are you. What are you saying with your. Your deeds, not your words? And you say this matters and this doesn't matter. And then, you know, Your decisions tell a very different story. I like to say, like, your calendar doesn't lie, and neither ultimately does your behavior at home.

[Sean Ryan]

Do you ever ask your kids for input on how you're doing?

[Ryan Holiday]

Oh, like, what can I do better? Yeah, all the time.

[Sean Ryan]

Do you really?

[Ryan Holiday]

Yeah.

[Sean Ryan]

What do they say?

[Ryan Holiday]

They're usually like, can I? You should give us our iPads more? Stuff like that. I. I think it's. It's a lot to ask them to be able to. I think when they're. They're older, they're going to be better at being able to verbalize, like, what. What they need more of and what they need less of. But I do try to think, like, hey, like, why isn't this working? You know, I try to, like, why, if this isn't having the effect that I want it to have, I need to do something differently. Instead of insisting over and over again that this is how it should go. This is, you know, this is what I think. But I don't know. It's a constant challenge. And one of the things I heard someone say that was helpful to me is the bad parents aren't thinking about whether they're doing a Good job or not. So the fact that it is a challenge and that you are thinking about it and that you're, you know, how are we doing here? What could we do better? I'm worried about this. Like, that's not. That already puts you in. In somewhat elite company.

[Sean Ryan]

You're a better parent by. Yeah, you're in the better parent category. Yeah.

[Ryan Holiday]

Yeah. Well, look, a lot of people have kids. Not everyone's a parent. Yeah. And the decision to be like, hey, I'm going to. I'm going to take this thing seriously. I'm gonna. It's not this side hustle that I have. It's like my main thing. It's the main reason I'm here. And I'm going to. I'm gonna work at this like I work at anything else, which means I'm gonna take it seriously, which means I'm gonna ask for advice, which means I'm gonna actually look at how it's going and the results. And then I'm gonna be willing to change and try. Try it differently. I'm not just gonna go, well, my parents did it this way, or, well, this feels right to me, but actually be willing to change and take feedback is not just change and take feedback. I think also apologize. There are things that 30 years later, if my parents apologized for, it would mean a lot to me. Right. I don't know about you, but if my parents were like, hey, you know what? When you were a teenager, you really clearly needed this, and we didn't do that for you, and I bet that was hard. And, like, we thought about it more and, like, we wish we'd done it differently. I'd be like, oh, my God. Right? So it's never too late, right, to apologize. How. How quickly can you do it now, though? Like. Like, can I go, hey, like the next day, hey, I don't know why I picked this fight with you about. You wanted to sleep on the floor. It doesn't matter to me. I just love that you still let me put you down. And picking a fight was not how I wanted it to go, but I did, and I don't want to do that. I'm sorry. I mean, I don't know about you, but I didn't get apologized too much when I was a kid. And maybe some people think that's weak or soft or whatever. To me, I'm trying to get better, and I'm not going to get better if I'm not taking accountability and responsibility for when I don't do it the way that I want to do it.

[Sean Ryan]

I do it. Especially about the phone.

[Ryan Holiday]

Yeah.

[Sean Ryan]

I feel so fucking guilty. And I keep doing it over and over and over again.

[Ryan Holiday]

Yeah.

[Sean Ryan]

But I. Paul, you know, I'm like, I do. I just. I have to do it.

[Ryan Holiday]

Yeah.

[Sean Ryan]

Because I think that, once again, a lead by example, because it also teaches them, like, they need to be able to do that, too.

[Ryan Holiday]

Or just to see you struggle with, like, you're like, hey, this is a thing I have to use, but I use it way more than I have to and I want to use it less. So here's where I want to be, and here's where I am, and here's your dad trying to get there. To me, that's a much more relatable, a much more inspiring and ultimately much more practical perception of your parents than mom and dad are perfect. Their word is law. Because kids know that's not true. They sense the bullshit and they resent it, and it undermines their connection and their belief in you. And so, yeah, I try to. I try to. To own that shit when I can. And I try to be. I try to be clear about the stuff that I'm working on and the stuff that I'm trying to get better at.

[Sean Ryan]

Yeah. Yeah. You know, I'm doing a. I got so much out of my first psychedelics ibogaine treatment. I'm doing it again in the. In the. In the foreseeable future. And what I'm really hoping I get out of it is some kind of perspective of what my kids think of me.

[Ryan Holiday]

Oh, interesting.

[Sean Ryan]

I really want to see what I look like through their lens.

[Ryan Holiday]

Yeah.

[Sean Ryan]

And that's probably going to be a hard thing to see, but, yeah, I. I just want to. I want to improve and I really want to see that.

[Ryan Holiday]

I saw this video of this billionaire, and someone was like, what's it like to have a billion dollars? Or what's it like to be rich? And he was like, rich? Isn't having a billion dollars rich is having kids who want to come home for the holidays. I think it's really important that you sort of define what success is. Right. Like, people go, oh, you only get 18 summers with your kids. And it's like, legally. But, like, you meet families and they spend a lot of time together, and you're like, oh, that's a whole different thing. I didn't know we could do that. You know, I didn't know that was something we could work towards. And so thinking about, like, what the goal is, and so the goal is not to have the shoes nicely lined up by the back door. The shoe that the goal is not to have. I remember I was talking to someone once. She was. She was in her 90s, and she's like, people used to come over and be like, it doesn't look like you have kids. And she was like, I took that as a compliment. And I. She's like, I don't know how I could have possibly been so wrong. She was like, your house should look like you have kids. You're like, you have kids. Why? What are you doing? So, like, the goal is to have. Is to not have these people for 18 years and then eject them and go back to your selfish life. Like, you started a family. The goal is to have the family.

[Sean Ryan]

Yeah.

[Ryan Holiday]

In the future. And so remembering that, running the things through the lens of that again, it doesn't mean giving them whatever they want whenever they want it, because that is also at odds with that. I would also say, though, like, if you're a billionaire, you can go visit your kids for the holidays. You know, they don't need to come home. But the point is, they should want. They should want to come home. Right. Like. Like you should. The success here is that. That when the authority ends, the relationship is still there. Yeah. And I think people lose sight of that.

[Sean Ryan]

I've never heard it like that. That's really good. Let's talk about speed reading.

[Ryan Holiday]

Oh, speed reading is a scam.

[Sean Ryan]

Well, how do I read faster?

[Ryan Holiday]

I don't know. I think it's illustrative that that's what you want to do. You're not like, how do I eat food faster? Is there a way to have sex faster? The point is stuff that's good, you want it to take how long it's supposed to take. So I don't know why we want to read faster. If the question is, how do I read more? I got lots of answers to that question, but I don't think we should try to read faster. I would say I read at a medium speed. I just spend a lot of time reading. And I spend a lot of time reading because it's worth doing. It's enjoyable to do, and also it's magic. The founding of Stoicism has a story about this. Zeno, the founder of Stoicism, he visits the oracle at Delphi, the famous oracle. And he asked what the secret to the good life is. And he's told that wisdom comes when we begin to have conversations with the dead. And it's only later at a bookstore that he realizes that that's what books are. It's a way to talk to people who are dead. That we can converse with Marcus Aurelius through meditations, that we can read the speeches of Churchill, that we can read the poems of Emily Dickinson, that we can read great novels, the campaigns of the greats. It's magic. It's fucking time travel. Here is someone who's no longer with us, transporting us to them, them to us, breaking down. You know, there's a famous poem that says, you know, books are door shaped like they're portals to another world. And so anyways, the point is reading is spectacular. Like for $15 or $20 or fucking free at the library, that you can have access to the brain of Julius Caesar or Napoleon. You know, you can read from Stockdale, you can read from Marcus Aurelius, you can read from Epictetus, you can read from Frederick Douglass, you can read from Abraham Lincoln. You know, this is incredible. Like the amount of wisdom and hard won experience inside the pages of the book is an incredible thing. And like most people are like, nah, I'd like to learn by trial and error. Or they're like, eh, I don't know. A lot of good stuff on Instagram too, right? It's ridiculous. Tolstoy talked about you can converse with the wisest people who ever lived and you choose not to. So I think first and foremost, understanding what reading allows you to do makes the ROI of it much clearer. Is it also entertaining and fun and relaxing? Sure. But it's an incredible thing that we have contained in these pages. The other thing is you got to make time for it. There's no shortcut. You got to do it, you got to make time for it. And if I looked at your screen time app, I promise you, I could find the time. You have the time, you're just not spending it. And this is for all of us. Like, I could read more. I just get distracted by things. And so one of the reasons I like carry a physical book with me everywhere is like when I sit down because I'm a little early or someone's late, or I have a few minutes between here or there. Like I want to read a book. I don't want to go into social media, I don't want to go into work. Like I want to read. And I see that as part of my job. Like it's crazy. Like some of my best ideas, some of the biggest successes I've had as an entrepreneur but also as an employee came from things I read in books. But for some reason, if Someone had come into my office, and I was sitting in a chair like this, reading. They'd be like, I don't pay you to do this yet. If I was sitting at my computer monitor checking espn, they'd have no idea. And so I think we need to do a better job understanding that reading is not just work, like, has a work benefit, but it's like, some of the best, single best way you could spend your time. And I know that's my case for reading. Right on, man.

[Sean Ryan]

Well, Ryan, I know you got a flight to catch, but this is amazing. This was an awesome conversation. I'd love to have you back at some point.

[Ryan Holiday]

I would be honored.

[Sean Ryan]

We do have a hot question. I almost forgot one last thing. Hot question. Audie Murphy tried to enlist in the Marines at 17.

[Sponsor/Ad Voice]

They rejected him for being too small.

[Sean Ryan]

The paratroopers rejected him, too.

[Sponsor/Ad Voice]

He finally got into the army by

[Sean Ryan]

gaining weight before the physical.

[Sponsor/Ad Voice]

5 5, 112 pounds.

[Sean Ryan]

He went on to win every US combat decoration for valor, including the Medal of Honor, 28 medals total. The most decorated American soldier in history. He came home, became a movie star, and was haunted by PTSD for the rest of his life. Slept with a loaded pistol under his pillow, got addicted to sleeping pills, locked himself in a hotel room and kicked a cold turkey. And then he did something nobody at his level was doing in the 1960s. He went public, talked openly about combat trauma, demanded the VA take it seriously. Died in a plane crash at age 45. Here's the question. Tell me about Audie Murphy. What does the smallest, quietest guy in the room becoming the most decorated soldier in American history tell us about what real toughness actually looks like?

[Ryan Holiday]

Well, they told us quite a bit about Audie Murphy right there. Just an incredible human being, an incredible American. He has a memoir called To Hell and Back, which I should have brought you because it's an amazing book. One of the great memoirs of the 20th century. I'll tell you one little story about Audie Murphy. All those accomplishments are incredibly impressive. One of the ones he doesn't get enough credit for, that. I think, in a way, it's not harder, but it's rarer. So he becomes a movie star, country musician, and he's asked to do a bunch of endorsements, and he turns down all drugs. Sorry, all cigarette and alcohol endorsements, because he doesn't want to model that for kids. And so, like, I just. I just think, like, he did a lot of feats of discipline and a lot of feats of courage, saying no to Money is a thing that a lot of brave and powerful people have found it hard to do. And I just, in a way that's like, there's physical courage and then there's moral courage and the moral courage to say, hey, I'm not going to do that. This doesn't feel right to me. Is courage that we don't celebrate enough. We don't give out medals for that kind of courage. And then the courage to speak out and to speak honestly about what you're struggling with, like, vulnerability, like, hey, I'm not okay. Hey, even though I'm capable of all these things, this thing is kicking my ass. I'm struggling with this thing. Again, that's another form of courage that, that we don't. We don't celebrate enough and we don't hold up enough. And, and it's, it's. And we wonder why it's, you know, we wonder why it's rare and, and. Moves me just, just as much. He's an incredible person. And you, you read some of those Medal of Honor citations for those guys and you're just. It's just absolutely unreal. Right?

[Sean Ryan]

Yeah. Yeah. There's a follow up here.

[Ryan Holiday]

Okay.

[Sean Ryan]

I think you're gonna like this. What does this story say to every influencer right now? Selling alpha males alpha male stoicism.

[Ryan Holiday]

Yeah, I, Andrew Tate is a fucking abuser of women. Shitty person, a sex trafficker. And the idea that, like, that's who you should be taking life advice from is insane. Right? Like, stoicism is not a recipe for making you a better sociopath. It is not this pick and choose thing where you take a couple motivational quotes and then you put it up next to an AI generated picture of Marcus Aurelius with a 12 pack, and you're like, I get it. It's a philosophy. And it's a philosophy built around virtue. And the four virtues of stoicism. Courage, essential. Discipline, essential. Wisdom, essential. But the fourth is justice. That's ethics. That's the standards you hold yourself to. That's your contribution to society, to the world. And none of the other virtues are of any worth if not balanced out by or in fact directed at justice. Right. Like courage on the battlefield. Sure. Very impressive. But what if you're fighting a horrible war? Like, I stayed in Franklin and, you know, walked past the Confederate statue, and, you know, it says there have never been braver men or a cause more honorable. It's like, I can think of quite a few causes more honorable, like, other than Nazism. It was literally the Worst cause. Like, literally the worst cause to ever go to war. For now, it's complicated. A lot of the men were drafted. Most of them didn't own slaves. They were told a bunch of lies by the slave powers. But let's not lie to ourselves about what that heroism was used for and what it would have looked like had it triumphed. Like, the world would have been a worse place. In fact, their virtue, that military valor, was weaponized and spent in the wrong way for the wrong cause. Right? And so there's no, like, that's ultimately what philosophy is designed to help us wrestle with. It's like, what's right and wrong? What do we owe other people? Are we making the world a better or a worse place? And look, if the ideas of masculinity and toughness and resilience, if that's what initially attracts you to stoicism, awesome, right? You just can't stop there. And I think probably you see this in your line of work, like, the recruiting poster is what gets the people in the door, right? But ultimately, you got to buy into the values and the cause larger than yourself. And that it. If that's not you, that's actually, like. Like the most dangerous person. Because, like, the violence and the power and the strength, all that stuff is, like, it's dangerous if. If not. If not moderated by and controlled by this ethical compass, it can become very addictive. Yeah. Yeah, that's a good question. Everyone should read To Hell and Back by Audie Murphy. Just like an incredible. An incredible book.

[Sean Ryan]

Right on.

[Ryan Holiday]

Yeah. Well, Ryan, dude, thank you.

[Sean Ryan]

Thank you, man. This was awesome. This was awesome. I really appreciate you coming. Had a great time. I hope you come back.

[Ryan Holiday]

Yeah.

[Sean Ryan]

Sweet.

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