Not Seeking Wisdom DESTROYS Great Minds | Ryan Holiday & Billy Oppenheimer

Summary

Podcast Summary: The Daily Stoic

Episode: Not Seeking Wisdom DESTROYS Great Minds | Ryan Holiday & Billy Oppenheimer
Date: October 25, 2025
Participants: Ryan Holiday (host, author of “Wisdom Takes Work”) and Billy Oppenheimer (researcher, writer, collaborator)

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Overview

This episode is the second part of a conversation between Ryan Holiday and his long-time research collaborator, Billy Oppenheimer, focusing on the dangers of neglecting wisdom, the perils that befall "great minds" who stop seeking it, and insights from Holiday’s latest book, “Wisdom Takes Work.” Drawing lessons from history and contemporary figures—particularly Elon Musk and Sam Bankman-Fried—the discussion explores mentorship, intellectual humility, and why unchecked intelligence easily devolves into folly. The tone is conversational, reflective, and at times irreverent, as the duo blends anecdotes, literary analysis, and personal stories.

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Key Discussion Points & Insights

1. The Path from Apprentice to Mentor (09:15–09:59)

• Ryan shares how his career began as Robert Greene’s apprentice, learning not just the craft of writing but a research and thinking method that now anchors his own books. He reflects on the cycle of teaching these lessons to Billy, and how mentorship is fundamental to both personal and intellectual growth:
  • “Seneca said of mentorship: For men learn as they teach. In helping others, we are forced to examine our own thinking, to reflect on our experiences.” (07:49)
  • The debt we owe isn’t just to our teachers, Ryan says, but to the next generation (“teachership”—James Stockdale’s term).

2. Elon Musk as a Cautionary Tale of Anti-Wisdom (09:15–25:07)

• Transition from Hero to Caution:
  Musk initially represented great accomplishment, but Holiday explains his contemporary transformation into a cautionary figure:
  • “He is a great man of history... and then there is this turn, which is fascinating to me because we used to—he was one of the few people that everybody agreed about... how he went from hero to villain so quickly and what happened.” (09:59)
• Dangers of Losing Intellectual Balance:
  The main lesson: Genius with no self-care, no feedback, no critical counterbalance devolves into delusion.
  • “This is what happens when you go from reading Soviet rocket manuals to figure out the rocket business from scratch to getting all your information from social media.” (11:59)
  • “This is what brain rot looks like—and this is what happens when you start to think you're a genius and you only hear from people who tell you what you want to hear. You become disconnected from reality extremely quickly.” (12:33)
• Family & Lineage Matter:
  Drawing from Jill Lepore’s profile and William F. Buckley’s biography, Holiday and Oppenheimer note how generational beliefs and pathologies are passed down—particularly Musk's background.
  • “The story of the son is always embedded in the father.” —Francis Ford Coppola via Billy (15:39)

3. The Isolating Effects of Success (21:26–24:54)

• Erosion of Feedback and Trust:
  Musk’s alienation is examined through his relationships: firing long-term assistants, the absence of enduring confidantes or critics.
  • “At that level, you need continuity and consistency... or else you become untethered.” (24:20)
  • “Success is in and of itself destabilizing. So if you don’t create stabilizers, you’re gonna fall off.” (24:54)
• Legacy of Mentorship:
  Contrasted to Musk, true greats keep close advisors for decades; the absence of this is a warning sign.

4. The Dunning-Kruger Curve of Genius: When Smart Becomes Stupid (25:07–38:59)

• Sam Bankman-Fried (SBF) as Cautionary Tale:
  Blind spots for “smart” people—hubris, lack of curiosity, and the “death of expertise.”
  • Holiday excoriates SBF’s famous dismissal: “If you wrote a book, you fucked up—it should have been an 800 word blog post. The hubris of that, the intellectual conceit of that...” (28:59)
• Glorification of Intellectual Burnout:
  Both Musk’s and SBF’s intellectual trajectories spiral as their social circles shrink and their info diets become echo chambers.
• Bad Bets and Overconfidence:
  The psychological danger of contrarian bets that come true.
  • “Making a contrarian bet that turns out to be right can be a brain-destroying experience... How do you go back to operating in the universe as a humble, regular person?” (33:16)
• Thin Air of Success:
  The more right you are against consensus, the more likely you start to believe you’re right everywhere—and the more isolated you become from reality.

5. Difference Between Smart and Wise (33:11–38:59)

• Humility v. Intelligence:
  “A lot of people are really smart and there’s not that many wise people. The tricky part about being smart is it makes you more susceptible to being really stupid.” (33:16)
• Staying Grounded:
  The ongoing challenge: remaining a student, seeking teachers, and accepting negative feedback.
  • “When was the last time you had a conversation and you were aware in the moment that you were the student and they were the master? And if that doesn’t happen on a regular basis, I think it deforms your perception of reality.” (39:28)

6. Mentorship, Feedback, and the Board of Directors (41:18–45:37)

• Historical Examples:
  Marcus Aurelius vs. Commodus: both had wise advisors, but one listened and the other didn't—leading to drastically different legacies.
  • “It’s interesting that Commodus and Marcus have basically all the same advisors and one is a philosopher king and the other is a monster who is killed by a gladiator. One listened and the other didn’t.” (41:30)
• Modern Creative Process:
  Ryan reflects on his own journey: why established authors must still actively seek feedback and not become complacent.
  • “I need to find... a John Landau type. How many people are going to say, ‘this isn’t your best work’?” (42:26)

7. The Haziness of Creative Feedback (43:14–44:57)

• Handling Negative Feedback:
  Ryan recounts his own insecurity over work (like “The Obstacle is the Way”) and how feedback can be both right and wrong.
  • "Is the lesson I shouldn’t listen?” (44:30)
  • “Nobody knows anything.” – quoting William Goldman (44:12)
• Outcome Unpredictability:
  Conflicting advice and unpredictable reception are inevitable, reinforcing the need for humility and persistence.

8. Writing, Growth, and Moving On (47:35–53:05)

• Reflections on the Virtue Series:
  Holiday is proud of growth across four books and reveals he’d love to go back and improve “Courage.”
  • “I wish now I could go back and write the Courage book again. That would be my dream.” (47:35)
• Perspective for New Writers:
  Billy discusses struggles with his own first book. Ryan emphasizes that the first book seldom defines an author’s legacy and the importance of finishing over perfection.
  • “This is probably not the book you were meant to write... This is like the experience job. You just need to do it. And that may require you accepting that you’re not going to do it on this one.” (53:05)
  • “The actual stakes are: do you do it right? And as long as you do it, you won.” (54:59)

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Notable Quotes & Memorable Moments

• On Mentorship:
  “For men learn as they teach. In helping others, we are forced to examine our own thinking, to reflect on our experiences.”
  — Ryan Holiday, quoting Seneca (07:49)

• On the Downside of Genius:
  “This is what happens when you go from reading Soviet rocket manuals... to getting all your information from social media. This is what brain rot looks like.”
  — Ryan Holiday (11:59)

• On SBF and the Death of Books:
  “If you wrote a book, you fucked up... It should’ve been an 800 word blog post. The hubris, the intellectual conceit of that.”
  — Ryan Holiday, on Sam Bankman-Fried (28:59)

• On the Self-Destructiveness of Intellectual Ego:
  “Making a contrarian bet that turns out to be right can be a brain-destroying experience.”
  — Ryan Holiday (33:16)

• Wisdom Versus Intelligence:
  “A lot of people are really smart and there’s not that many wise people. And the tricky part about being smart is that it makes you more susceptible to being really stupid.”
  — Ryan Holiday (33:16)

• On Seeking Out Teachers:
  “When was the last time you had a conversation and you were aware in the moment that you were the student and they were the master? And if that doesn’t happen on a regular basis, I think it deforms your perception of reality.”
  — Ryan Holiday (39:28)

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Timeline of Important Segments

• 09:15 – Apprenticeship and paying it forward
• 09:59 – Elon Musk’s journey from admired innovator to cautionary tale
• 11:59 – How intellectual isolation leads to brain rot
• 15:30 – The father-son dynamic in great (and infamous) men
• 21:26 – The danger of losing critical feedback and continuity
• 28:59 – Sam Bankman-Fried’s intellectual arrogance about books
• 33:16 – Why smart people do stupid things
• 39:28 – The necessity of being a student, no matter your stature
• 41:18 – The difference between good and bad kings (and modern creators): listening to advisors
• 47:35 – Holiday’s wish to rewrite his own early work
• 53:05 – Advice and perspective on writing a first book

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Takeaways

• Wisdom is a process, not a possession: Even the most brilliant minds can derail if they neglect feedback, mentorship, and self-awareness.
• Intellectual humility is vital: Contrarian successes are dangerous if they breed unchecked ego.
• Mentorship benefits both parties: Teaching is a way to deepen your own learning—and it breaks the cycle of hubris.
• Keep learning, keep questioning: No matter your accomplishments, you’re vulnerable to folly if you’re not regularly the student, too.
• Creative risks and feedback are inseparable: Self-doubt and advice (sometimes conflicting) are both necessary—and ultimately, the act of finishing is what matters most.

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This episode is a must-listen for anyone interested in the difference between wisdom and intelligence, the importance of mentorship (both giving and receiving), and the subtle dangers that come with success. Ryan Holiday and Billy Oppenheimer’s candid, story-driven conversation is equal parts cautionary tale and practical instruction for lifelong learners.

Transcript

[Ryan Holiday]

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[Jeff Bridges]

Morning, Zoe. Got donuts.

[Ryan Holiday]

Jeff Bridges.

[Dana]

Why are you still living above our garage.

[Jeff Bridges]

Well, I dig the mattress and I want to be in a T mobile commercial like you teach me so Dana.

[Dana]

Oh no, I'm not really prepared. I couldn't possibly at t mobile get the new iPhone 17 Pro on them. It's designed to be the most powerful iPhone yet and has the ultimate pro camera system.

[Jeff Bridges]

Wow, impressive. Let me try. T Mobile is the best place to get iPhone 17 Pro because they've got the network. Nice.

[Dana]

Jeffrey.

[Ryan Holiday]

You heard them.

[Jeff Bridges]

T Mobile is the best place to.

[Ryan Holiday]

Get the new iPhone 17 Pro on us with eligible traded in any condition.

[Jeff Bridges]

So what are we having for lunch?

[Dana]

Dude, my work here is done.

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[Ryan Holiday]

Welcome to the weekend edition of the Daily Stoic. Each weekday we bring you a meditation inspired by the ancient Stoics, something to help you live up to those four Stoic virtues of courage, justice, temperance, and wisdom. And then here on the weekend, we take a deeper dive into those same topics. We interview Stoic philosophers. We explore at length how these Stoic ideas can be applied to our actual lives and the challenging issues of our time. Here on the weekend, when you have a little bit more space, when things have slowed down, be sure to take some time to think, to go for a walk, to sit with your journal, and most importantly, to prepare for what the week ahead may bring. Hey, it's Ryan. Welcome to another episode of the Daily Stoic podcast. I think that the path to mastery, to wisdom, to success, usually involves two things and they kind of bookend each other, right? So it starts as, as my career did, with what Robert Greene calls the apprenticeship phase. I began as an apprentice to Robert. That's how I learned how to write. That's how I learned the research method that I build all my books around. Robert taught me that. And then I in turn, and this is maybe not exactly the end of my career, but it's certainly a transition phase where then I taught that to my research assistant, Billy Oppenheimer, who has become a great writer in his own right and was the interviewer on this kind of turn the Tables episode that we brought you part One of earlier in the week, he and I sat down and talked about the new book and how it got made and how we work together and all that stuff. But I taught that to Billy, and he's now working on his first book, so there's that transition. But one of the chapters that I have in Wisdom Takes Work that I'm very proud of is about that, the sort of paying it forward. Actually, it's a theme in a couple of the books. It's the Coaching Tree chapter in Right Thing. Right now I have a chapter in part one about finding your teacher, and then I have a chapter in part three about becoming a teacher. So let me actually bring you a little segment of that chapter, because it's one of my favorites. Wisdom cares about progress, not itself. Each of us is only a vessel and not a permanent one. It is inevitable that we will all be replaced eventually. Knowledge is power, they say, but like power given to Antoninus, it has strings attached. We owe something to our teachers. We owe something to someone else now, too, to future generations. And that debt, as Stockdale described it, is teachership. But we are wrong to see this simply as charity, as some onerous moral obligation. We get something out of it. The process is mutual. Seneca said of mentorship for men learn as they teach. In helping others, we are forced to examine our own thinking, to reflect on our experiences. We sit down and write, putting what was previously intuition into knowledge. And in writing this for someone else, we practice empathy and understanding. Feynman would actually say that if someone can't do this, if they can't clearly and simply explain what they know to someone else in simple terms, it's because they themselves don't fully understand what they think they know. We learn as we teach. Someone was our mentor. Who are we mentoring? We've had our board of directors, but whose board are we on now? That's what it's about. We've got to go back into the cave. We have to bring others out into the light with us. And so, you know, obviously, as I was putting that together, I was thinking about Billy. I was thinking about my time with Robert Crean. I'm thinking about the other researchers and employees that I've been lucky enough to work with, some who've gone on to do really awesome things. Very proud of all of them. Billy's new book is coming out, which I'm excited about as well. I don't think it has a publicly stated title yet. He's got to finish it. And Billy, if you are listening to this, although I doubt you are. I tend not to want to listen to things that are about me either. Got to finish this book, man. Let's get it across the finish line. In any case, you can check out Billy's wonderful newsletter, the Six at Six on Sunday. You can find [e-mail] and as I was saying, it's been one of my favorite things, like as rewarding as any success I've had. A bunch of different people have come in and gone, is Billy here? Can I meet Billy? Or Billy will come down when we do the walkthroughs to the store and they're like, oh, I get your newsletter. I know who you are. I just love that. That's what it's all about. That's the paying it forward. He's gotten better for his work with me, but I have gotten better working with him. Not just his contributions, but in teaching and thinking about these things. That has been immensely instructive to me. And as I talk about in the justice book, the third book in the Virtue series, Wisdom is four. It's been immensely rewarding too. So this is part two of my conversation with Billy Oppenheimer, talking about the new book Wisdom Takes Work. It would mean so much to me if you could still order it. This first week is where it's all at. Grab it on audible. Grab it as an ebook. Grab it as. Grab the signed editions from the painted [e-mail] Wisdom Swing by the Painted Porch, Swing by Barnes and Noble. I don't care where you get it. It just means a lot to me that you order it. And I can't wait for you to check out the book. Thanks to Billy for his work on the book. Thanks to you for supporting the other books in the Virtue series. And I'll just get into this episode.

[Billy Oppenheimer]

Trying to think like, how do we segue into part two of the book? Yeah, Musk as a cautionary tale. And that part just being like some of the anti Wisdom.

[Ryan Holiday]

Yeah.

[Billy Oppenheimer]

Things to avoid.

[Ryan Holiday]

He's the only one in the whole series. There's some cautionary tales, but he's the only. Like I tried to pick one really impressive person for part one, part two, part three of each book. Like I different than obstacle. He goes. I would really do like a very big deep dive into characters. So did Florence Nightingale and de Gaulle Tain, Queen Elizabeth, Lou Gehrig, Gandhi, Lincoln. But I think Elon Musk is the only one that is negative. I mean, the story starts very positive because he is a great man of history. Like the others. But then there is this turn, which is fascinating to me because we used to. I think he was one of the few people that everybody agreed about. Like, it is fascinating to me how he went from hero to villain so quickly. And what happened.

[Billy Oppenheimer]

Yeah.

[Ryan Holiday]

Like, when people go, Elon Musk, then people might go, what happened to that guy? That is itself interesting. So that's what that one's about.

[Billy Oppenheimer]

Yeah.

[Ryan Holiday]

And that was harder because it's also something that's, like, happening. And I. Like, the Doge stuff happened after I finished.

[Billy Oppenheimer]

Yeah.

[Ryan Holiday]

So then I had to add some stuff back. But, like, that was a developing story. That was a weird one, too. But those are harder because, like, I felt like I had more of a hotter take when I wrote it. And then I feel like I've been subsequently vindicated by events.

[Billy Oppenheimer]

Yeah.

[Ryan Holiday]

In a way that, although satisfying intellectually, might make some of the arguments feel less singular. But I think when I was writing them in 2023. Yeah, they were a little fresher.

[Billy Oppenheimer]

Yeah. At some stage you had. I don't know if concerns the right word, but just like, a lot of people would maybe disagree with this take.

[Ryan Holiday]

Sure. Yeah.

[Billy Oppenheimer]

But now.

[Ryan Holiday]

Yeah, you'd be there. If you don't. When you look at him and you see if you're not like, whoa, that's. Something went sideways there, you're probably also brain fucked.

[Billy Oppenheimer]

Yeah.

[Ryan Holiday]

Which again, is not to say that he's not incredibly impressive. It isn't gonna continually to do impressive things. I think that's what. Actually, the hard part about writing the chapter is that, like, at every step of Elon Musk's career, what he's doing has seemed crazy, and betting against him is a very bad bet. So I had to spend a lot of time trying to figure out if this moment is different and why it's different and what there is to learn from it.

[Billy Oppenheimer]

What would you say is, like, the. The big lesson from him of what not to do?

[Ryan Holiday]

I mean. Well, this is what happens when you don't take care of yourself, when you have no balance in your life, when you have no structure in your life. And a lot of it was. Is informed by my experiences at American Apparel, where I watched a different kind of genius become untethered. But to me, the most salient is, like, this is what happens when you go from reading Soviet rocket manuals to figure out the rocket business from scratch to getting all your information from social media.

[Billy Oppenheimer]

Yeah.

[Ryan Holiday]

Like, there is. People go, oh, podcasts are great. Or, oh, you know, I've really curated social Media or whatever. Like, this is what brain rot looks like, and this is what happens when you start to think you're a genius and you only hear from people who tell you what you want to hear. You become disconnected from reality extremely quickly.

[Billy Oppenheimer]

Yeah.

[Ryan Holiday]

Also, there's a really fascinating piece in the New Yorker that Jill Lepore wrote about his grandfather and father. His grandfather was, like, this sort of, like, quack doctor who moved to South Africa because of its views on racial segregation. Like, before it was an apartheid state. Like, he went there to participate in it becoming an apartheid state and was a conspiracy theorist who, you know, is, like, anti Semitic and sexist and racist and unhinged, you know? And when you read that, suddenly the current musk doesn't seem like an independent creation. It seems like the natural evolution of that lineage, which is like. Have you read anything in that William F. Buckley's book I was telling you about?

[Billy Oppenheimer]

Yeah, I'm like, a third of the way in.

[Ryan Holiday]

The book's incredible, is it not?

[Billy Oppenheimer]

It's really good.

[Ryan Holiday]

Like, to be able to make a compelling biography of someone you would not give a shit about is, like, a very impressive feat. But have you read much about his father yet? Is that, oh, Buckley's father isn't at the beginning, maybe not very far, but you go, oh, you understand the father, and then suddenly you can't separate the son did not independently come to all the ideas of the father.

[Billy Oppenheimer]

Yeah.

[Ryan Holiday]

The son heard them from the father, believed them, and then created intellectual justifications for. Like, there's a scene where William F. Buckley's siblings go and burn a cross on one of their neighbor's lawns. And then you're like, oh, but he was an intellectually rigorous conservative. It's like, no, you were raised in a bigoted family that when desegregation happened, your father put his money into a segregationist newspaper. Your father dispatched you to tell your sister that she could not marry your best friend from college because he was Jewish. Like, you did not independently come to these controversial ideas, but not from a place of bigotry if your bigot father had all the same views and you grew up with that person. So, like, you have to trace this stuff back. And then you go, oh, okay. They're able to present it as this, but when you have the larger context.

[Billy Oppenheimer]

There'S a video of Francis Ford Coppola. Yeah, it's one of those where he's, like, walking through all of his movies, and he has a line in there of the story of the son is always embedded in the Father.

[Ryan Holiday]

Yeah, sure.

[Billy Oppenheimer]

And that's kind of like what he's exploring in a lot of his movies.

[Ryan Holiday]

Yeah, yeah, yeah, that's totally what it is. That's not to say that, like, it had to go this way.

[Billy Oppenheimer]

Yeah.

[Ryan Holiday]

But if it did go this way, it did not independently go this way. Right. Like, it's obviously rooted in the example, and then whatever the predilections are in a person that make, you know, like the paranoid style did not strike twice like lightning. Like, you had a paranoid, reactionary father and you became just a more palatable and socially adept paranoid style reactionary. That doesn't mean everything you said was bad. That doesn't mean you weren't smart. That doesn't mean you weren't a great writer. That doesn't mean you weren't a great political organizer. All those things are true. Just like Elon Musk is clearly not as extreme as his grandfather. His father is a, it appears, a sex predator who had children with one of his stepchildren. Okay, so is Musk a pro natalist because he did all this research about declining birth rates and blah, blah, blah, blah, blah, and he really cares about the future of civilization? Or did he grow up in the house of a sexual predator and he picked up some weird fetishes and stuff and that's this.

[Billy Oppenheimer]

Furthering civilization is just the story to justify it.

[Ryan Holiday]

And again, this doesn't change the fact that he's a brilliant engineer or whatever. What I'm fascinated by is, like, if your great grandfather or your grandfather was an anti semitic, racist, conspiracy theorist, quack physician, might you, in the middle of a pandemic, go, if my instinct is to be anti vaccine, anti science, anti public health, could these two things be related or. What is fascinating about reading biographies is that this stack of pages makes you understand the person better than they understand themselves in some ways. And how rare self awareness is.

[Billy Oppenheimer]

Yeah.

[Ryan Holiday]

Not to say I have it, because if you think you do, you almost don't. Certainly don't. But the point is, it's fascinating how quickly the trajectory or the underlying forces in a person's life can be made clear to everyone but themselves. Thanks to Toyota Trucks for sponsoring this episode. When I bought my ranch in 2015 out here in Bastro County, I drove my car about halfway down the dirt road that we live on. Thought, this isn't going to work. Stopped, parked it walked the rest of the way home, borrowed my wife's car, drove into Austin and bought a truck. What I bought was a Toyota Tacoma. And this truck wasn't just transportation. It was getting me to and from my house. It unlocked a whole different style of living for us, not just on the ranch, but in our little Texas towns. There were places I could go now that I couldn't go before, especially out here in the piney forests, through the fields and on the unpaved roads like the one that I lived in. We got to go deep into the Hill Country's wild beauty. We've driven all the way out to East Texas. We've driven it across the country. And by we, I mean not just my wife, but both my kids, who I drove home from the hospital in that truck. Toyota trucks are built for those who understand that the best adventures happen when you're willing to veer off course. Because you never know when you'll end up on a Toyota Adventure Detour. And of course, this is stoicism too, because every detour, every obstacle is an opportunity. But it's helpful if you can handle the difficulty inherent in that. If you've got the resilience and the right companion to make it wherever the road takes you, discover your uncharted territory. Learn [e-mail] Trucks Adventure detours by the time you know you need someone new on your team, you're already behind, right? You don't need to hire someone tomorrow, you need to hire somebody new yesterday. So how can you find amazing candidates fast? Easy. Just use Indeed. When it comes to hiring, Indeed is all you need. Stop struggling to get your job post seen. Indeed's Sponsored Jobs helps you stand out and hire fast. And with Sponsored Jobs, your post jumps to the top of the page for relevant candidates so you can reach the people you want faster. According to Indeed data, Sponsored Jobs post directly on Indeed have 45% more applicants than non sponsored jobs. And plus, with Indeed sponsored Jobs, there's no monthly subscription, no long term contracts, and you only pay for results. People were hired on Indeed while you were listening to this. That's how fast it is. There's no need to wait any longer. Speed up your hiring right now with Indeed and listeners of this show will get $75 sponsored job credit. To get your jobs more visibility@ Indeed.com DailyStoke just go to Indeed.com DailyStoke right now and support the show by saying you heard about Indeed on this podcast. Indeed.comDailySTOIC Terms and Conditions apply. Indeed is all you need.

[Billy Oppenheimer]

And he almost seems to like cut ties with anyone who's willing to like there's a great story.

[Ryan Holiday]

The Sam Harris thing?

[Billy Oppenheimer]

No.

[Ryan Holiday]

Oh, they made a bet during the pandemic for like quite a bit of money. But not obviously to Elon Musk about how Covid would go. And at some point Sam Harris like followed up and Musk was like refused to acknowledge or pay up. Yeah, that's pretty funny.

[Billy Oppenheimer]

Well, there's the story you tell of the. I don't care if it's Tesla or somewhere else, but an employee kind of stands up to him and he's like, I disagree with like what you said.

[Ryan Holiday]

Immediately 1% of the population would fall for this thing that you just fell for. Like this is like elite level stupidity here, you know. And Musk is like, fuck you. Get the fuck out of, you know, fires him.

[Billy Oppenheimer]

Yeah.

[Ryan Holiday]

And then he looks around the room and he's like, why isn't anyone else talking? You know, like I have some experience with that because I like Dove at American Apparel would just fucking scream at people. And I think this new documentary, someone told me there's some scenes of it, but like I've seen the chilling effect that like that sort of feral like feral power slash anger issues, like what it does to people. So yeah, you add, I mean there's this great letter that Twain writes to Vanderbilt and he goes, you think you're a genius, but you're not understanding the way that your sense of yourself is the reflection off your 70 million. 70 million, which is like the, the largest fortune in the world at that time. Which gives you a sense of how crazy society has got. Like 70 million. I mean, Musk bought Twitter for 44 billion.

[Billy Oppenheimer]

Yeah.

[Ryan Holiday]

And it was like a rounding error to him. But just, just to be successful at any level is alienating and isolating and the air gets thinner. But then if you eschew human interaction for an unhealthy amount of online mob dynamics, it is as toxic an environment as you can imagine building around yourself. I thought in the Ashlee Vance book, I think it's in there. Maybe it's in the Walter Isaacson book. But there's this scene where he fires, when he's only running SpaceX and Tesla, he fires his assistant and doesn't replace them. And that was like 15 years ago or 10 years ago. Now of course, part of it might be pretends that he doesn't have anyone helping him, but the fact that there's not, he doesn't have a long time person who is his. Like when I was working on the Raveling book, yeah, he was like, call. And he said this name. Who? I won't say because maybe it's private, but he's a call this person. And it was like Michael Jordan's assistant of like 30 years.

[Billy Oppenheimer]

Yeah.

[Ryan Holiday]

You know, you need. At that level, you need continuity and consistency.

[Billy Oppenheimer]

Yeah.

[Ryan Holiday]

Or else you become untethered, you know? And the idea that a person who's just on its face running an inhuman amount of companies and businesses at an inhuman pace with the stakes as high as they are, that he would be fucking winging it is.

[Billy Oppenheimer]

Yeah. And just like, what does it say that no one's stayed in his circle for.

[Ryan Holiday]

Yeah.

[Billy Oppenheimer]

A long time.

[Ryan Holiday]

Yeah.

[Billy Oppenheimer]

Like Rav had like, relationships for 60 years.

[Ryan Holiday]

No, no, you. You need that. It's not healthy and it's. It's destabilizing. Like, success is in and of itself destabilizing. So if you don't create stabilizers, you're gonna fall off.

[Billy Oppenheimer]

Another cautionary tale in the book is sbf.

[Ryan Holiday]

Oh, yeah.

[Billy Oppenheimer]

And his.

[Ryan Holiday]

Although it's funny, that will probably get pardoned and then that story won't seem as.

[Billy Oppenheimer]

I still think he's.

[Ryan Holiday]

Well, of course. No, no, I'm just saying. I'm just saying, like, we live in a time where that should be a universal cautionary tale.

[Billy Oppenheimer]

Yeah.

[Ryan Holiday]

Just as Musk should be a universal cautionary tale. And instead, somehow these things have become partisan and almost like litmus tests. Like, you can't see the thing that should be obvious to everyone under any circumstances, even if you are predisposed to like, that person.

[Capital One Announcer]

Yeah.

[Ryan Holiday]

Yeah. And I thought people have criticized that Michael Lewis book as being positive. I think he, like, destroys him in that book, but he does it so artfully that it doesn't feel like that's what he's doing. Because Michael Lewis is a seeming. I've never met him, but like a happy, well adjusted person who seems to love celebrating unconventional characters.

[Billy Oppenheimer]

Yeah.

[Ryan Holiday]

And yeah. To me, that it is a withering picture of him, that none of you wouldn't say that about any of his other books except for maybe the Jim Clark in the New New Thing, which is a great book that more people should have read. It feels it's probably going through a cycle where. Because tech has changed. There was a period where it didn't seem that impressive because it's like the founder of Netscape. But now that so much time has passed, it probably comes back around, like reading about Rockefeller or something. But there's some scenes in the New New Thing where he's like playing a tuba alone in his room and you're just like, oh, it's sad to be you, you know, but mostly, mostly Michael Lewis's portraits are very positive.

[Billy Oppenheimer]

Yeah. That sad to be you line made me. There's something about, like, forget who said it, but it's like, if you're so successful, why are you so miserable?

[Ryan Holiday]

Yeah. Yeah. Or if you're so smart, why aren't you happy? I've heard it said something like that.

[Billy Oppenheimer]

And Musk, like, there's just some really sad clips of him out there of just like, wow, you wouldn't want to be. And he says that, you know, like, you wouldn't want to be me.

[Ryan Holiday]

I was at a party and I was talking to someone, and they were asking me about the wisdom book, and I was telling them about it, and then I slowly realized that they were. They were very connected to Musk. I won't say how. I'll tell you later how they were connected, but I put two and two together and they were like, oh, I can't wait to read the book. And I was like, I'm not sure you do.

[Billy Oppenheimer]

Had you told them that.

[Ryan Holiday]

No, no. They were just. We're talking about wisdom, generally virtue and wisdom. They had, like, a philosophy degree. They were, like, excited.

[Billy Oppenheimer]

Yeah.

[Ryan Holiday]

And then they were like, oh, I'll start with that one. And I was like, please don't.

[Billy Oppenheimer]

Or maybe that's like, the person who needs to read it.

[Ryan Holiday]

Yeah. When I tell you who this person is, you'll get. I don't want to blow them up or embarrass them. But that was a weird part of that. Right. Because, like, they just announced, like, another million square feet they're adding to the SpaceX offices, like, two miles from here.

[Billy Oppenheimer]

Yeah.

[Ryan Holiday]

Like, if you look at, like, if you get, like, an alert from Twitter or whatever over email and you look at the bottom, it's like, Twitter is headquartered in Bastrop now.

[Billy Oppenheimer]

Yeah.

[Ryan Holiday]

It's crazy, right?

[Billy Oppenheimer]

Like, so you're saying, like, it would have been much easier to not include him in the book in this way.

[Ryan Holiday]

I just already know how many. We did a piece the other couple weeks ago that you helped me with and the amount of angry emails about it.

[Billy Oppenheimer]

Yes.

[Ryan Holiday]

Like, it's. I just already know. And then people are all that what they're going to write is like, how could you. Like, didn't you understand this was going to piss someone like me off? It's like, I do. I would just like not to have to hear from you about it.

[Billy Oppenheimer]

Yeah.

[Ryan Holiday]

You just keep it yourself.

[Billy Oppenheimer]

But the part two, like, the watching your info diet, not breaking your brain.

[Ryan Holiday]

Yes.

[Billy Oppenheimer]

And there's a great story of sbf like with a journalist of like, I.

[Ryan Holiday]

Never read a book.

[Billy Oppenheimer]

Being very skeptical of books.

[Ryan Holiday]

He said that I would never. He was like, if you wrote a book, you fucked up.

[Billy Oppenheimer]

Yeah.

[Ryan Holiday]

It should have been an 800 word blog post. The hubris of that, the intellectual conceit of that. I mean he's obviously incredibly smart. He can do things with numbers in a way that he could probably sit here and just. Our jaws would be on the floor. Like he'd probably be one of those people that could divide two credit card numbers in his head or something. He's obviously a genius. But then you go, oh. Layered on top of that genius was fundamental incuriosity, a fundamental ego and a fundamental antisocial tendency that in the end unraveled the genius and brought you crashing back down to earth. The idea that the thing that has been responsible for the progression of human wisdom over thousands of years, that these things are better expressed as an 800 word blog post. So the audacity of that and then it's also just perfectly encapsulated and encapsulates where we are as a society. This sort of death of expertise, the death of real knowledge. It is the, the Seneca story about, well, I'll just get someone to whisper into my ear.

[Billy Oppenheimer]

Yeah, yeah.

[Ryan Holiday]

And that's sufficient. And it's, it's both terrifying and tragic.

[Billy Oppenheimer]

Yeah.

[Ryan Holiday]

I thought was interesting about that is that that came with this interview. There's an interview. Some guy who's writing for one of the VC companies, sort of like an in house publication.

[Billy Oppenheimer]

Yeah.

[Ryan Holiday]

Doing that interview. And like he has the, a little bit of an argument with him. This guy who's a professional writer.

[Billy Oppenheimer]

Yeah.

[Ryan Holiday]

Goes, well, you know, he's so smart. He's probably smarter than me. Maybe he's onto something.

[Billy Oppenheimer]

Yes.

[Ryan Holiday]

And it's like, no, he's a fucking moron. That is one of the dumbest things that a person has ever said on the record to a journalist. Just putting aside whether it's true or not. That's a dumb thing to say to a writer who is interviewing you and holds your fate in their hand. Like most writers would have. That would have changed the entire direction of the piece and it would have become a takedown. Like that was just a reckless thing to do. Putting aside the fact that it's just dumb and wrong. That's just a dumb thing to say. Like, know your audience. That's a dumb thing to say. Yeah, that's a dumb thing to say when you are spending hundreds of millions of dollars to buttress your public image. To make you look like a super genius. That's just a dumb. That's a thought you might have. And a lot of books are fuck ups and do suck, but that's just a dumb thing to say. Yeah, but I thought it was. Watching the mental gymnastics of this writer to justify an indictment of his own profession. And life's work is also interesting.

[Billy Oppenheimer]

Well, yeah, and he like, the piece is like kind of glowing.

[Ryan Holiday]

Yeah, no, that's what I mean. He's like, he knows more than me. He's such a genius. That should have been an emperor has no clothes moment, but instead it's the opposite, which is a big one. I talk a lot about cognitive dissonance in part two of the book. That is classic cognitive dissonance. I can either like, that guy's having to look at one of the richest people in the world who just said something so profoundly stupid that it should make you question everything they think about everything. And instead of doing that, which is hard also because he's being paid by the VC company to profile this person instead of being like five alarm fire. This is crazy. I don't know if this guy is what he thinks. He's like, no, no, no, no. He's more than, I think, like, he's actually like even smarter. And again, I've done that. It's easier to think that than to go, oh fuck, now I have to be at cross purposes with this person.

[Billy Oppenheimer]

Yeah. I think the writer even has like a moment of questioning.

[Ryan Holiday]

Like there's a little back and forth and then he's just like, no, no, no, I'm gonna side with you.

[Billy Oppenheimer]

But no, like questioning his own, like.

[Ryan Holiday]

Oh, maybe like, yeah, maybe I wasted my life. Yeah, yeah, it's pretty, it's pretty spectacular.

[Billy Oppenheimer]

How do you think about the difference between being wise and being really smart?

[Ryan Holiday]

Well, a lot of people are really smart and there's not that many wise people.

[Billy Oppenheimer]

Yeah.

[Ryan Holiday]

And I think the tricky part about being smart is that it makes you more susceptible to being really stupid.

[Billy Oppenheimer]

Yeah.

[Ryan Holiday]

Because you like. One of my friends who gave me some great notes on the Musk chapter, he said this thing I think about all the time. He said making a contrarian bet that turns out to be right can be a brain destroying experience. And I think that's kind of one of the explanations for the radicalization of Silicon Valley in a very short amount of time is it's not good for your sense of self and your ability to continue to operate in the world, to have gotten something very right while everyone else is telling You. You're wrong. And then to have been proven right. Because then how do you go back to operating in the universe as a humble, regular person who's not right about everything?

[Billy Oppenheimer]

Yeah. And it's just an entire population of people who have had that experience, at least.

[Ryan Holiday]

And then you layer on top of that money, fame, bubble, et cetera. This is also what happens. Elon Musk. Right. It's hard to go, I was just right about this one thing and then every other thing I'm starting over from scratch on. I think about this, like, writing the obstacles away and it dramatically exceeding expectations and bringing sort of creating this whole sort of resurgence of an ancient philosophy. That doesn't mean that every idea that I have is that.

[Billy Oppenheimer]

Yeah.

[Ryan Holiday]

In fact, statistically, it's much more likely that my next idea is not that. And so the story you tell yourself, your relationship to reality, this is all tenuous stuff because it's not even a contrarian bet, just making any kind of bet that pays off. It doesn't change. You're starting from scratch each time.

[Billy Oppenheimer]

And then each time you get more and more sort of emboldened by these people are wrong. Because I have proof that it takes.

[Ryan Holiday]

A lot of discipline to start from first principles every time and to not go. These people are fucking wrong about everything. So if I think this I'm right and they're wrong, that's. I think that is maybe the number one reason why smart people do stupid things. There's a section in the book where I just sort of list, like, all the dumb things that, like, really genius people fell for.

[Billy Oppenheimer]

Yeah.

[Ryan Holiday]

And I think this is partly why, like, a lot of people that I knew that were sort of groundbreakers in these various things are now have a lot of kind of fringe, either political or medical beliefs, is that it was hard for them to be right about. Largely right about Paleo. Like, the food pyramid is 100% wrong. Like, not what your diet should be. You should not be mostly eating grains and rices and breads and shit. Right. It's not. That's not what we're meant to eat. And that's not. Now the food pyramid was. You could argue that those are the cheapest foods. And if you're trying to feed as many people as possible, like, there's some political logic to it too. But the point is they were totally right. You know, does that mean you should only be eating, you know, like, this carnivore diet? No. Like, that's probably not right either. But you should. It's very hard to Be say, like, really right about Paleo. And then everyone make fun of you and be like, oh, you're gonna eat like a caveman, you idiot, you know, and get made fun of. And it turns out that, you know, they were largely right or their stuff helped a lot of people or whatever. Or they. So just at a personal level, they weighed this and they look like this. They made these changes, and now they weighed this and they look like this. And then, you know, I think you're gonna be more vulnerable to, like. And maybe the vaccine shouldn't be trusted or whatever. Right. Like, when you've had a contrarian bed, it makes it. You start to see that everywhere.

[Billy Oppenheimer]

Yeah. And, like, what else is wrong if the food pyramid. Have you read the Marc Maron memoir from, like, early in his career?

[Ryan Holiday]

Oh, the. Yes.

[Billy Oppenheimer]

I forget that. He tells a story of, like, when he was in a period of that, like, just sort of questioning everything. And he goes to meet a friend who was working in D.C. and he's like, what are you doing? Like, can you see this is all. And he just is, like, asking about all these different conspiracies. And his friend is like, mark, we're not that organized. And it was like. It broke him in a good way of, like, it's just people going to work every day, like.

[Ryan Holiday]

Yeah. And that's not to say there. There aren't some conspiracies. I mean, I wrote a book about one. That's not to say there aren't. Isn't some coordination there. There aren't very popular beliefs that you should question. You know, anytime you're on the Twain's thing, like, anytime you're on the side of the majority. Pause and reflect. Yeah, but there's a difference between pausing and reflecting and instinctively, intuitively being against it. And that's like Peter Thiel, I remember, said to me, he's like, contrarianism. He's like, I don't like being called a contrarian because that means I just take what everyone believes in. I put a minus in front of it. And I think when Peter's been right about stuff, it's because he was independently correct. But I do think you're watching his trajectory isn't anything like Elon Musk. But there's certainly been. I think you can certainly trace not an overconfidence, but a destabilizing effect that having been right about a lot of things, has had. And that can take you to some kooky places, especially when most of the people you engage with intellectually want something from you or are dependent on you in some way or are afraid of you. And that's the root thing for Elon Musk. When was the last time Elon Musk had a conversation with someone and he thought that person was smarter than him? Probably a very long time. Yeah.

[Billy Oppenheimer]

Whoa.

[Ryan Holiday]

And I guess that's a good question for everyone. Like, when was the last time you had a conversation and you were aware in the moment that you were the student and they were the master? And if that doesn't happen on a regular basis, I think it deforms your perception of reality.

[Billy Oppenheimer]

Yeah.

[Dana]

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[Ryan Holiday]

You.

[Billy Oppenheimer]

You have the chapter in Part 2 of Board of Directors and the story of Commodus. A sort of ancient example of refusing to listen to.

[Ryan Holiday]

Yeah, it's interesting that Commodus and Marcus Krus have basically all the same advisors and one is a philosopher king and the other is a monster who is killed by a gladiator. And it's that one listened and the other didn't. I mean, Nero has the best advisors you can imagine too. And he's an interesting case because you have kind of a control for the first five years. He's widely seen as a pretty good Roman emperor. There's a Quinium Neuronis, like the five golden years of Nero. And then what happens? He kills his mother and then he stops listening to Seneca and it devolves from there. I've been thinking about this. With even something I'm dealing with on the book right now. I can basically write whatever I want and I don't have to listen to any of the edits from my publisher. That's not a healthy place to be and that's not a place that's conducive to getting your best work.

[Billy Oppenheimer]

Yeah.

[Ryan Holiday]

So I'm trying to figure out how to fix that. I need to find not a new editor, but I need to find. I need to find a, A John Landau type.

[Billy Oppenheimer]

So we talked about that shift from Google Docs into a Word document is like a big step in the process. And then the next time I see it, you send me the full Word document and you're like, if you had to cut 10% of this, which 10% would it be?

[Ryan Holiday]

Yeah, but how many people are going to say like, this isn't your best work? Although actually I do remember I sent the obstacles away to someone, an editor I really liked. And I was like, I honestly don't know if this is like publishable. It just felt weird to write these like 366 discrete independent things and slapped together to call it a book. Like I, it was unlike anything I'd done and there weren't, Wasn't really. I just didn't know if it would work.

[Billy Oppenheimer]

Yeah.

[Ryan Holiday]

And I had like some very strong second thoughts before I sent it into the publisher and this person was like pretty negative on it themselves.

[Billy Oppenheimer]

Yeah.

[Ryan Holiday]

Like more negative than I was. And I, I took some of their advice. Other. Anyways, then it came out and it's all like crazy.

[Billy Oppenheimer]

Yeah.

[Ryan Holiday]

So what do you take from that?

[Billy Oppenheimer]

Right.

[Ryan Holiday]

Like, this is what I mean. It's very hard to know what lessons to take from things and how to stay sane is the challenge.

[Billy Oppenheimer]

Yeah, but. And then with a creative project, like, it's so difficult to know because it's just like a question of taste and like, do you trust that person's tastes?

[Ryan Holiday]

Yeah. Maybe they were right. Maybe, maybe their criticism was totally right and it could have been better. Maybe the criticism was right and it's a fluke that it sold. You know, there's like, it's impossible to know what lesson to take from this other than intellectual humility like William Goldman's like, nobody knows anything. Nobody knows.

[Billy Oppenheimer]

Yeah.

[Ryan Holiday]

Is it meaningful and interesting to you? Have you done your best?

[Billy Oppenheimer]

Yeah.

[Ryan Holiday]

Was it challenging to do? You're on steadier ground when you think about those.

[Billy Oppenheimer]

So what happened that you get the negative feedback from the editor? Obviously the book ultimately was published.

[Ryan Holiday]

Yeah, that's what I'm saying. I don't know. I mean, I obviously didn't listen, but so is the lesson I shouldn't listen. That's what I mean.

[Billy Oppenheimer]

Yes. That could have been one of the takeaways of never listen to editors.

[Ryan Holiday]

And then I could have sent in the next book and it could have been actual shit. And then if someone told me it was actual shit, I'd be like, well, you were wrong last time.

[Billy Oppenheimer]

Yeah.

[Ryan Holiday]

Like, when Elon Musk was starting SpaceX, his friends had an actual intervention. Like they sat him down and had an AA style intervention. So when some people were like, Twitter's a bad idea, why would he listen?

[Billy Oppenheimer]

Yeah. What was it that you ultimately, you said you weren't sure it was publishable.

[Ryan Holiday]

You're always insecure about it.

[Billy Oppenheimer]

Yeah.

[Ryan Holiday]

And then I think I read it a couple more times. I. I think I made some improvements. I think I addressed where I thought I was weak. And then also I trusted some other people. You know, my agent thought it was good. That's Steve, who I worked on it with. My publisher thought I was good. Samantha thought I was good. And then also. So what, you know.

[Billy Oppenheimer]

Yeah.

[Ryan Holiday]

What happens if you're wrong?

[Billy Oppenheimer]

Yeah. I wanted to ask about Obstacle Ego Stillness became a trilogy.

[Ryan Holiday]

Yeah. I mean, are they a trilogy? They're just, They're. Sure you can buy them in a box. Yeah. They're. Other than. Stylistically, there were three discrete ideas, largely. There were three distinct ideas influenced by stoic philosophy.

[Billy Oppenheimer]

Yeah. In this series, you set out knowing it was going to be four books.

[Ryan Holiday]

Sure.

[Billy Oppenheimer]

What were the challenges or differences of, like. Because one book, you know, is like.

[Ryan Holiday]

Well, all the courage stories are basically justice stories or they're not good stories. It's like, let me tell you about this courageous person who was robbing banks or whatever. This courageous person who conquered and raped and murdered for. No, like all, you know, it's, it's. They're all related. That was the tricky part of the series is even Zeno 2500 years ago said they are, like, distinct but inseparable from each other. And I think that's about as well said as you can say it.

[Billy Oppenheimer]

Yeah.

[Ryan Holiday]

Like, none of them work in isolation. All of them inform each other and they are each made up of Sub virtues, which also have overlap with each other.

[Billy Oppenheimer]

Yeah. I forget which chapter it was that went. Got pushed through the whole series.

[Ryan Holiday]

Yeah. Which one was that? Did it end up making it in the book at all?

[Billy Oppenheimer]

I can't remember. But it's an interesting example of how stuff was able to work in each of the four books.

[Ryan Holiday]

We should find out what chapter that was. There was one that started in Courage, moved to Discipline, moved to Justice. And then I think I thought I was going to go on Wisdom, and I don't know if it did.

[Billy Oppenheimer]

Yeah. I can't remember.

[Ryan Holiday]

We should find that.

[Billy Oppenheimer]

Yeah.

[Ryan Holiday]

But, yeah, there was a bunch of chapters, and then obviously I kept pushing note cards. There's probably two or three thousand unused notecards from the whole series that I was just like, I'll push this, I'll push. And then I just never ended up using it. So there was just a lot of that. And I wish now I could go back and write the Courage book again. That would be my dream.

[Billy Oppenheimer]

Really?

[Ryan Holiday]

Yeah. I mean, I think I'm a much better writer.

[Billy Oppenheimer]

Yeah.

[Ryan Holiday]

I mean, I don't think I would do it from scratch, but I would just. I'd beef it up a little bit. Maybe I will at some point. I don't think I'd touch the other three, but I think Courage a little more. Just because it's like Courage. It's like the intro for Wisdom. Like it was in the ballpark of what I wanted. Kind of my head. I could leave it, but I discovered some things doing the other three books.

[Billy Oppenheimer]

Yeah.

[Ryan Holiday]

That I would tighten up on. Even just. I mean, the first one, you're coming up with the style, but then you're also perfecting it on 2 and 3 and 4.

[Billy Oppenheimer]

Have the quote from Gibbon in the afterword of when he completed Decline and Fall. Yeah.

[Ryan Holiday]

Yeah. About taking leave from an old friend.

[Billy Oppenheimer]

Yeah. How does it feel to take leave from the series?

[Ryan Holiday]

You know, not as bad as I thought it would be. I mean, I did. I have liked knowing that I've got this sort of clear trajectory and what I'm supposed to be working on. And everything I'm researching is so everything you read can fit in one of those four. But I'm so excited about the next. That's been the tragedy of the blessing and the curse of the track I've been on is that I always in the middle of what I'm doing next as I am promoting and talking about the one I'm just putting out.

[Billy Oppenheimer]

Yeah.

[Ryan Holiday]

So, like, I would love to just be nerding out about the one I'm in, but it's. That won't come out for 18 months.

[Billy Oppenheimer]

Yeah. So the next three are in various stages.

[Ryan Holiday]

Is it three or four? What do I have? Yeah, at least three. Wait. Yeah, I have three. But some of them are one's. Kind of a greatest hits album.

[Billy Oppenheimer]

Yeah.

[Ryan Holiday]

Kind of a thing I've got.

[Billy Oppenheimer]

Yeah.

[Ryan Holiday]

We do it all.

[Billy Oppenheimer]

I think we did it all.

[Ryan Holiday]

Right, so I have a question for you.

[Billy Oppenheimer]

Yes.

[Ryan Holiday]

What's going on with your book?

[Billy Oppenheimer]

It's been a real head game.

[Ryan Holiday]

Why is it a head game?

[Billy Oppenheimer]

I think a lot of, like, the insecurity of. Is this good scrapping it feeling it could be better. I've had a lot of stops and starts with different ways of structuring it.

[Ryan Holiday]

And are you still with the last one we talked about, or did you scrap that? Scrapped. Really?

[Billy Oppenheimer]

Yeah. And now I. I think where I'm at now is, like, not needing to know the structure before writing. And now I'm just writing. And I remember I was talking to James Clear, like, a year ago, and I asked him, when did he come to the four parts of Atomic Habits? And it was like he had finished the book.

[Ryan Holiday]

Yeah.

[Billy Oppenheimer]

And realized, oh, they fit in. And so now I'm, like, trying to do that of just, like, writing the main things. I want to get into the book.

[Ryan Holiday]

And then the thing I would say.

[Billy Oppenheimer]

Yeah.

[Ryan Holiday]

And this is where I think you're a little stuck. And that's why I was telling you the story about Daily Stoic is. I bet he didn't figure that out. I bet that emerged from the process further along in the process than you currently are.

[Billy Oppenheimer]

That's what I mean.

[Ryan Holiday]

Yes. No, no. But what I mean is that I'm sure that that came once the book had been submitted in some way. Like, I think you might be hoping that there's some moment when it all becomes clear to you and you feel good about it. That's like, you don't feel good about it literally until after it comes out. Like, I felt concerned about this book as I was reading the audiobook in this room. So I think you are sometimes taking the thing down to the studs because you're not feeling a certain way about it. And maybe closer, you may need to come to terms with the fact that you will never feel the way that you're feeling.

[Billy Oppenheimer]

Yeah.

[Ryan Holiday]

And if you are to get to the place that you need to get to, chances are you are not going to be the sole originator of that feeling. It's going to come from and it's not good to be motivated by other people, but I think you might need the sensation of doing it. And then them going, this is awesome. And then me reading going, this is great. I think you are expecting to feel a certain way that you are not capable of feeling because one, you're you. But two, no one ever feels that way.

[Billy Oppenheimer]

Yeah.

[Ryan Holiday]

But you should have some sense of this because you've seen some other books go through the process. But like, you saw the manuscript, this book, or a lot of my books, and then you saw the finished one. Obviously I'm the reason it got from here to there, but I'm not the only reason it got from here to there. And part of it is just the process itself. Part of what you're feeling is the fact that it's between two covers and it's designed and all the titles are, you know, like, that's a post production feeling, not a word document feeling.

[Billy Oppenheimer]

Yeah.

[Ryan Holiday]

You know what I mean?

[Billy Oppenheimer]

Yeah. But I'm still struggling with like, it needs some sort of arc or like.

[Ryan Holiday]

But I think you think you are gonna figure that out and you're. You're not fully taking advantage of the collective knowledge around you. Like, you think Robert Greene couldn't figure that out or give you a pretty good piece of advice or Rick couldn't look at, you know, like there's other people.

[Billy Oppenheimer]

You're right.

[Ryan Holiday]

I think you're expecting yourself to have the ability to solve a complex problem that you've not solved before.

[Billy Oppenheimer]

Yeah.

[Ryan Holiday]

So maybe you'll do it, but it'll just take you an unlimited amount. And also the other thing is, like, this is not supposed to be your. Sometimes it works out as it did for James or Mark Manson, where their first book comes out and it's this monster thing that almost certainly will not be the case.

[Billy Oppenheimer]

Yeah.

[Ryan Holiday]

And this is probably not the book you were meant to write. I'm not saying it's not a book you were meant to write.

[Billy Oppenheimer]

Yeah, yeah. No, I know what you mean.

[Ryan Holiday]

But this is probably your 1 of 6 or 1 of 16. You don't know. So you have to do it. This is like the experience job. You just need to do it. And that may require you accepting that you're not going to do it on this one.

[Billy Oppenheimer]

Yeah. Use the example of Michael Lewis meeting the Moneyball idea.

[Ryan Holiday]

Yeah, yeah. He had to do like 10 books to get there or whatever. You don't know what that is. It could be. You could meet that on this. Your second idea could be that. But chances are this is not how most people are going to interact. This is not the thing that most people who are going to read your stuff.

[Billy Oppenheimer]

Yeah.

[Ryan Holiday]

Will even read.

[Billy Oppenheimer]

I also, like, I want it to be do, like, well enough to earn the right to do another one.

[Ryan Holiday]

And so it's like most people get two shot. Like, you have to really. That would be another thing. You have to really fuck this up to not get another shot. You might not get a shot with these people, but you're starting here. Do you know what? I'm. You're not like, hey, I got a walk on audition at this for this. Like, you got drafted very high. Like, you signed a major book deal with a major publisher that has pretty high expectations, but not insane expectations. So, like, the degree to which you have to fuck up to not get a second chance is, like, almost impossible. As far as finishing a book now, if you don't finish it and you have to push it again. Yeah, you could be the person that. That never arrives. But if you do the thing, there's no universe in which it flops so hard that you don't get a second try. So you got to figure out the actual stakes are not how it does.

[Billy Oppenheimer]

Yeah.

[Ryan Holiday]

The actual stakes are do you do it right? And as long as you do it, you won.

[Billy Oppenheimer]

Yeah.

[Ryan Holiday]

Thanks so much for listening. If you could rate this podcast and leave a review on itunes, that would mean so much to us and it would really help the show. We appreciate it. And I'll see you next episode.

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[Ryan Holiday]

Look, ads are annoying. They are to be avoided if at all possible. I understand, as a content creator, why they need to exist. That's why I don't begrudge them when they appear on the shows that I listen to. But again, as a person who has to pay a podcast producer and has to pay for equipment and for the studio and the building that the studio is in, it's a lot to keep something like the Daily Stoic going. So if you want to support a show but not listen to ads. Well we have partnered with Supercast to bring you a ad free version of Daily Stoic. We're calling it Daily Stoic Premium and with Premium you can listen to every episode of the Daily Stoic Podcast podcast completely ad free. No interruptions, just the ideas, just the messages, just the conversations you came here for. And you can also get early access to episodes before they're available to the public. And we're going to have a bunch of exclusive bonus content and extended interviews in there just for Daily Stoic Premium members as well if you want to remove distractions, go deeper into Stoicism and support the work we do here. Well it takes less than a minute to sign up for Daily Stoic Premium and we are offering a limited time discount of 20% off off your first year. Just go to Dailystoic.com premium to sign up right now or click the link in the show descriptions to make those ads go away.