The Obstacle Is the Way

“I remember my book, The Obstacles Away, made its way through professional sports.”

“So anyway, somehow Oprah went from Maria to my books. And I know she went to my books because as we were talking, I could see Oprah's marked up copy of The Obstacle is the Way.”

“I think that's right cuz look, I I wrote this book, The Obstacle Is the Way, and I think people it's been it's meant something to people and I think, you know, generally the idea is true that there's an opportunity in everything.”

“Oprah had read The Obstacle Is the Way.”

“and then even like I just did the 10 year anniversary of the obstacles away and um I was like they were like can you re-record the audiobook and I was like can I just record the new sections and you plug them in and They were like, "Go listen to the audiobook."”

“May I don't know if I tell it maybe it's in obstac in the obstacles way but I I don't know if I ever if if I told that story in writing anywhere but yeah.”

“So I I have the obstacles away tattooed here as a reminder. And then I have ego is the enemy tattooed here.”

“so there's I me people tell me they just read the obstacles away it's been out for 12 years or whatever”

“well so I put um phosphorescence in I I'm doing a 10y year anniversary edition of the obstacles away and I use one of your stories in it a yeah fun I the you talked about”

“I've included phosphorescence in a ten-year anniversary edition of The Obstacle Is the Way, and I used one of your stories.”

“like when Marcus really says the obstacle is the way yeah I think people have taken that because that's how I I wrote the first book they've taken the obstacles away to mean here's how you get ahead in business”

“they've taken the obstacles away to mean here's how you get ahead in business here's how you deal with these little disadvantages you turn them into springboards”

“I was thinking about the obstacles way in my early 20s primarily as a means to overcome professional obstacles.”

“What if we started with the understanding that many people resonate deeply with this book?”

“If someone thinks, 'Well, I've read that book,' why would they want the 10th anniversary edition?”

“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.”

“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”

“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.”

“Having to listen to the audiobook of The Obstacle is the Way, I barely recognized my own voice; that is a surreal experience.”

“So when I was writing The Obstacle is the Way, it was about popularizing and making interesting something many did not think was interesting.”

“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.”

“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.”

“originally The Obstacle Is the Way was in the business category. And so uh it very much stood out.”

“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.”

“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.”

“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.”

“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.”

“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?"”

“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.”

“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.”

“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.'”

“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.”

“Well, I learned that on 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.”

“like yeah like you know the the passage that I have helped popularize this one from Mark seris about how the obstacle is the way”

“because I remember I was I finished the manuscript for the obstacles away on a flight from Sydney to Perth”

“No, I I also try to remind myself of what, because I remember I was, I finished the manuscript for The Obstacle Is The Way on a flight from Sydney to Perth. Oh wow, uh, and three off fly, I just, I just finished it, I sent it in and I had zero idea that it would do as well”

“Yeah, you know, because I think 'Obstacle is the Way.' I also think ego is an obstacle—your own. It's the biggest obstacle, your own sort of sense of your entitlements, you know, where you should be in life.”

“so I just did a 10-year anniversary edition of the obstacles away which it hasn't come out yet but a lot of athletes I you know I mean a lot of uh I work with the US ski team quite a bit and a lot of the skiers use it or I recommend it to them”

“i lived there when i wrote obstacle actually”

“so like when the obstacles away came out it did okay i didn't hit any bestseller list the publisher was sort of like you know”

“I mean, I have a weird relationship with my first book, which is like a version of myself that I don't see myself as anymore.”

“because Tim and I have a long-standing mutual affection for stoicism and he actually published the Audi book of the obstacle is the way so I've known Tim forever”

“He actually published the audiobook of The Obstacle Is the Way, so I've known Tim forever.”

“As you’ve mentioned, obstacles away sold a great number of copies, but you received a modest advance. The publisher’s hesitance reflected the dynamic values you expressed earlier; it may not feel fair on the surface initially, but building on smaller wins has its benefits.”

“In your case, truly the obstacles away sold incredibly well over time, closing the loop on the early takes of its career and growth.”

“when you asked me about self-publishing earlier when I experienced this unintentionally and intentionally when the obstacles way came out”

“When you asked me about self-publishing earlier, I experienced this unintentionally and intentionally when 'The Obstacle is the Way' came out.”

“but for a week and then you know I had to take a big step back when I sold the obstacles the way”

“I think I got lucky in the sense that, you know, I did a book when my first book came out when I was 25 and it hit a bestseller for a week, and then, you know, I had to take a big step back when I sold The Obstacle is the Way.”

“someone told me they thought it would sell 5,000 copies the obstacles away and that it would sell”

“Like with The Obstacle Is the Way. When The Obstacle Is the Way came out, first off, it didn't hit any bestseller list the week it came out.”

“Like with 'The Obstacle is the Way,' when 'The Obstacle is the Way' came out, first off, it didn't hit any bestseller list the week it came out.”

“And so, the lesson I try to take from The Obstacle Is the Way is not I'm a genius. I wrote a book that, you know, popularized a school of philosophy and and sold lots of copies.”

“One of my favorite quotes from Marcus Aurelius, which I actually remember thinking about when 'The Obstacle is the Way' came out, is as follows: 'We love ourselves more than other people, yet we care about other people's opinions more than our own.'”

“so my favorite for Marcus which I actually remember thinking about when the obstacles the way came out”

“oh and the OB which which I ultimately did with the obstacles away but the obstacles away didn't come out till 2014 ... the hardest thing it was so hard but he was totally right because if I was if I'm now looking back the obstacle and what is the way and I'm like I'm a little young it would”

“Well, you asked me about self-publishing earlier; I experienced this unintentionally and intentionally when The Obstacle is the Way came out. Uh, I’d already sold the sequel and so in one respect that probably cost me a lot of money because The Obstacle is the Way did, over the next year or two, start to do really well.”

“It's funny, when I had, I wrote The Obstacle is the Way, I sold Ego is the Enemy, which was in the middle of writing, and my agent, Steve Hanselman, came to me and said you should do a book of a daily devotional of Stoicism.”

“yeah it's important obviously I wrote this book the obstacles way which is about how you take the sort of lower case te traumas obstacles difficulties and you find a way to move forward from them to use it to your advantage”

“yeah it's important obviously I wrote this book the obstacles way which is about how you take the sort of lower case te traumas obstacles difficulties and you find a way to move forward from them”

“Yeah, it's important; obviously, I wrote this book, The Obstacle is the Way, which is about how you take the sort of lowercase 't' traumas, obstacles, difficulties, and you find a way to move forward from them to use it to your advantage. You know, the computer... goddammit!”

“So yeah know yeah very um but I and I think the obstacle way the the obstacles the way had just come out. So that would have been my first book about stoic philosophy”

“But I think 'The Obstacle Is The Way' had just come out, um, so would have been my first book about stoic philosophy and then 'The Daily Stoic' would have come out a little bit later than that.”

“and and that goes back to the obstacle is the way sure because if you don't you're gonna hit this”

“And, um, I actually—I had to go back through and read some of my earlier books. I’d reread The Obstacle is the Way and what I was struck by, what I noticed there for the first time was that there was a tightness to the writing and the book is shorter.”

“I mean, like if you if you I would not recommend writing a book called The Obstacle Is the Way, a book called Ego Is the Enemy, a book called Stillness Is the Key, a book called Courage Is Calling, Discipline Is Destiny because then people expect you to be all those things”

“If you, I would not recommend writing a book called 'The Obstacle is the Way,' a book called 'Ego is the Enemy,' a book called 'Stillness is the Key,' a book called 'Courage is Calling,' or 'Discipline is Destiny.' Because then people expect you to be all those things, which is of course impossible.”

“Like I didn't I didn't feel like I was getting robbed when I took like less than half for The Obstacle Is the Way as I'd gotten for Trust Me, I'm Lying.”

“I sat down to write it like 2, and it was actually really great to talk about 'The Obstacle's Way.' It was this perfect reminder of like this is why I don’t start my day at 2.”

“so trust my mind my first book is to is it is 10 years old this summer is 10 years old yeah and and actually obstacle came out eight years ago yesterday”

“This summer is 10 years old; and actually, 'Obstacle,' came out eight years ago yesterday, which is also like insane to me when I read stuff that I wrote that long ago.”

“In 'The Obstacle', I tell this story about Edison when his Menlo Park laboratory burned down.”

“like I remember one time I was writing in obstacles the way because I was working on that when I attended I was writing about um astronauts being sent into space and how they do emotional regulation”

“Like I remember one time I was writing in Obstacles the Way because I was working on that when I attended, I was writing about astronauts being sent into space and how they do emotional regulation. And then I'm sitting down at dinner and Jim Lovell is just like at the table across from me and I was like, oh”

“I remember I was working at American Apparel well after I'd written The Obstacle, come out.”

“the obstacle is the way it came out in 2000 may of 2014 and it didn't hit any last”

“When I did The Obstacle is the Way, I've told this story before, but it wasn't that everyone rejected it.”

“And there was this whole thing which I wrote about, and that happened the day that I ended the book tour for The Obstacle Is the Way.”

“So, like you were asking me about having a job; one of the benefits—like when my publisher offered me what was not as much money as I would have hoped for The Obstacle Is the Way, I was like, ‘Sure, whatever,’ right?”

“the first year that i worked with him he sent me ego's enemy and the obstacles away”

“no in my book uh the obstacles the way i talk about arthur ashe you know his the amount of pressure the amount of horrible things he had to endure”

“His books like The Obstacle Is the Way, Ego Is the Enemy, The Daily Stoic have all reached number one New York Times best-seller status, and Stillness Is the Key appears in more than 40 languages, and all of his books have sold more than 4 million copies.”

“like when when The Obstacle Is the Way came out, just just to just to sort of illustrate this idea that nobody knows anything. Um, the publisher offered me half what they'd offered me for my first book for what was my second book.”

“And I think like one of the benefits for me when I was thinking about writing The Obstacle Is the Way, and I've talked about this before, but my publisher offered me half what I got for my first book for what was supposed to be my second book.”

“I was wondering, are you comfortable telling the story of how you ended up hearing about 'The Obstacle Is the Way'?”

“And his books, which include "The Obstacle Is the Way," "Ego Is the Enemy," "The Daily Stoic," "Stillness is the Key," and his latest offering and the focus of today's conversation, "Courage Is Calling" right here have sold altogether over four million copies.”

“but the obstacle is the way it came out probably four years after that and it what my mentor was totally right”

“the obstacle is the way show me again the obstacle is the way it's the way and it's gonna be your way you're unique you're one of a kind diamond this is my first book about philosophy the obstacle is the way”

“If you'd love a signed copy of The Obstacle is the Way, Ego is the Enemy, Stillness is the Key, the leather bound edition of the Daily Stoic.”

“the obstacle is the way so this this is from from what I read about it this this statues from 1840”

“I bought this when I was writing The Obstacle Is the Way.”

“Ryan Holiday (TW/IG: @RyanHoliday) is one of the world's foremost thinkers and writers on ancient philosophy and its place in modern life. He is a sought-after speaker and strategist and the author of many bestselling books, including The Obstacle Is the Way, Ego Is the Enemy, and The Daily Stoic.”