Episode · The Daily Stoic · 2024-10-09
Books mentioned on Turn the Tables | Ryan Holiday Reflects on 10 Years of The Obstacle Is the Way
Today, the tables have turned as Ryan Holiday is interviewed by his research assistant, Billy Oppenheimer, to talk about the 10th Anniversary Edition of The Obstacle Is the Way.
Books mentioned, in the order they came up
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The Obstacle Is the Way
The Obstacle Is the Way by Ryan Holiday is a popular guide to modern stoic philosophy that teaches readers how to turn everyday hurdles into opportunities for growth.
Discussed“Like I I imagine there's a lot of people who this book means a lot to. That means a lot to me. It was It was a really impactful book. Um at various times in my life. And if if somebody thinks, "Well, I've read that book." Yeah. Why would they want the 10th anniversary edition?”
Where to get it
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Papyrus
Papyrus by Irene Vallejo is a narrative history of books and the written word in the ancient world, tracing the origins of libraries, scrolls, and literature.
Recommended“Actually, I just read this book called Papyrus which is incredible.”
Where to get it
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Meditations
Meditations by Marcus Aurelius is a collection of personal reflections and Stoic philosophy written by the Roman emperor.
Discussed“Like, you look you can look at sales of Marcus Aurelius's Meditations and like, you know, they sort of flat and then The Obstacle Is the Way comes out and they spike a little bit over the intervening years and then in 2020 they just like go through the roof.”
Where to get it
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The Boy Who Would Be King
The Boy Who Would Be King by Ryan Holiday is a biographical examination of early leadership, virtue, and character development through historical figures.
Discussed“Um, what how we should wrap up is, okay, how do you determine— Um, like I was listening to your episode with Rich Roll recently, and he was like, 'My favorite thing in this book in the Justice book was the afterward where you do insert yourself into it.'”
Where to get it
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Essentialism
Essentialism by Greg McKeown is a practical guide to personal development and productivity that advocates focusing on the vital few things while eliminating non-essential tasks.
Discussed“And he, he sort of went out of his way to—I forget which book it was—but you did a similar thing where it was a story about you.”
Where to get it
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The Daily Stoic
The Daily Stoic by Ryan Holiday and Stephen Hanselman is a practical philosophical guide offering 365 meditations on wisdom, perseverance, and self-mastery drawn from ancient Greek and Roman thinkers.
Discussed“So, so that I was never going to be in The Virtue books, but then I did realize, okay, if you're talking about virtue and you're making strong judgments—positive and negative—of other people, um, there can be an implication that you're somehow the master of these things.”
Where to get it
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Ego Is the Enemy
Ego Is the Enemy by Ryan Holiday is a philosophical guide that examines how unchecked ambition and self-importance obstruct success, urging humility instead.
Discussed“Yeah, yeah, so I went through a similar thing on Ego Is the Enemy; there's a preface to Ego Is the Enemy that I'm in.”
Where to get it
Other mentions in this episode (34) — ad reads, self-promotion and passing references, never counted
Own book The Obstacle Is the Way
“I was thinking about the obstacles way in my early 20s primarily as a means to overcome professional obstacles.”
Own book The Obstacle Is the Way
“What if we started with the understanding that many people resonate deeply with this book?”
Own book The Obstacle Is the Way
“If someone thinks, 'Well, I've read that book,' why would they want the 10th anniversary edition?”
Own book The Obstacle Is the Way
“Well, you know, I feel like I've read that book because I wrote it, and then I had this unique experience during the pandemic where I was reading some of it to my son, primarily to help him sleep.”
Own book Ego Is the Enemy
“I mean, there's whole people in in in Ego's Enemy I have this whole chapter about Ulysses S. Grant that certainly reflects my opinion of him then, but my if I was writing it now it would be very different cuz I have a better opinion of him.”
Own book Ego Is the Enemy
“In Ego is the Enemy, I have this whole chapter about Ulysses S. Grant that reflects my opinion of him at that time.”
Own book The Obstacle Is the Way
“And so with the 10-year anniversary coming up, the the publisher asked if there was anything I wanted to do, and I said, "Why don't we just do like a whole updated edition?" And they were excited about that. Also, because 10 years ago was long enough that audiobook rights were very different, and they kind of uh sold the”
Own book Trust Me, I'm Lying
“And I did this on I did this on Trust Me, I'm Lying, also, but I think that was like a 5-year anniversary edition, because like stuff in the media changes faster than this.”
Own book Trust Me, I'm Lying
“I did this with Trust Me, I’m Lying as well, but it was like a 5-year anniversary edition because stuff in the media changes faster than this.”
Own book The Obstacle Is the Way
“Having to listen to the audiobook of The Obstacle Is the Way and barely recognize the voice of yourself, that is a surreal kind of mindfuck of an experience.”
Own book The Obstacle Is the Way
“Having to listen to the audiobook of The Obstacle is the Way, I barely recognized my own voice; that is a surreal experience.”
Own book The Obstacle Is the Way
“So when I was writing The Obstacle is the Way, it was about popularizing and making interesting something many did not think was interesting.”
Own book The Obstacle Is the Way
“There's lots and lots and lots of parts of The Obstacle Is the Way I'm very proud of. But, if you can reread something you wrote or worked on a long time ago, and you think it's perfect, I mean, to me that's a sign that you haven't gotten any better since you've done it.”
Own book The Obstacle Is the Way
“And so yeah, when I was writing The Obstacle Is the Way, it was hey, let me tell you about this thing called stoicism. And the task was much more along the lines of popularizing and making interesting a thing that a lot of people did not think was interesting.”
Own book The Obstacle Is the Way
“originally The Obstacle Is the Way was in the business category. And so uh it very much stood out.”
Own book The Obstacle Is the Way
“I mean, I didn't I someone else told me it later, too, that they they thought they their prediction for The Obstacle Is the Way was that it would sell like 5,000 copies.”
Own book The Obstacle Is the Way
“well, one of the big flaws of The Obstacle Is the Way is that there's just not enough female stories in it. Mhm. It's just like That's a criticism I got from many people over the years.”
Own book The Obstacle Is the Way
“And I would say that when I was writing The Obstacle Is the Way, I was much closer to my time having worked for Robert Greene.”
Own book The Obstacle Is the Way
“And I would say that when I was writing The Obstacle Is the Way, I was much closer to my time having worked for Robert Greene. So I would say I was also more I was more amoral in not immoral.”
Own book Ego Is the Enemy
“if I had predicted any of this for The Obstacle Is the Way, I shouldn't have been allowed to write Ego Is the Enemy. be in an institution.”
Own book The Obstacle Is the Way
“And we got connected by someone and he said, "Oh, I've read your book The Obstacle Is the Way." And I said, "Oh, that's insane. How did you hear about it?"”
Own book The Obstacle Is the Way
“So sure, if The Obstacle Is the Way had failed and been this embarrassing, painful, devastating thing, then yeah, The Obstacle Is the Way would have been a chance to practice stoicism.”
Own book Ego Is the Enemy
“Well, and it just never it never there's it uh in Ego's Enemy I have this quote from John Wheeler, the physicist. He says, "As your island of knowledge grows, so does the shoreline of ignorance."”
Own book Ego Is the Enemy
“Well, and it just never—there's this quote from John Wheeler, the physicist, in Ego Is the Enemy.”
Own book Ego Is the Enemy
“In Ego's Enemy I have this quote from John Wheeler, the physicist.”
Own book The Daily Stoic
“Like I'm finishing, I'm on—basically, I've probably got like 10% left of the first draft of the fourth book in The Virtue series, and I'm much more comfortable.”
Own book The Obstacle Is the Way
“Was there anything when you went back through The Obstacle on this past read, and you're like, 'Oh, I forgot how I did that.”
Own book The Obstacle Is the Way
“Yeah, so I wrote it, I've published it, I've read it, I've talked about it for 10 years, then I rewrote it or like rewrote chunks of it, edited it, went through copy editing, went through production design on it, and then I read the audiobook and I was like, 'This is horrible.'”
Own book Trust Me, I'm Lying
“So I I did I think two versions of the two versions of Trust Me, I'm Lying.”
Own book The Obstacle Is the Way
“So I did I think two versions of The Obstacle or two versions of Trust Me, I'm Lying; I think this is my—I’m getting this 10 years apart on The Obstacle Is the Way, and then I've obviously reread stuff that I've written even further ago than that.”
Own book Stillness Is the Key
“So I have noticed like even in The Obstacle, Ego, Stillness, each one is a little bit longer than the one that came before it.”
Own book The Obstacle Is the Way
“Well, I learned that on The Obstacle Is the Way.”
Own book The Obstacle Is the Way
“Well, I learned that on The Obstacle Is the Way. So, if you read the first draft of The Obstacle In my mind, I'm not in The Obstacle Is the Way. Like it's it's a book about all these other people. And I don't remember putting a single I or me in the book.”
Own book Ego Is the Enemy
“So I went through a similar thing on Enemy. And there's a preface to Ego's the Enemy that I'm in for that reason.”