Book · 2014 · Business & Economics
The Obstacle Is the Way
The Timeless Art of Turning Trials into Triumph
Why people recommend it
The Obstacle Is the Way by Ryan Holiday is a widely read introduction to Stoic philosophy that reframes personal hardships and trials as opportunities for growth and resilience. Chase Koch mentioned on Conversations with Tyler that the book heavily influenced his adoption of Stoic principles. Chris Williamson recommended the work on Modern Wisdom as a helpful resource for physical recovery and overcoming adversity. Billy Bush discussed on The Megyn Kelly Show how he befriended the author and utilized the book's Stoic framework to navigate challenging life events. Patrick Dempsey appeared on The Daily Stoic to discuss an anniversary edition of the book, highlighting its practical application for athletes facing unexpected equipment failures and weather delays. Ali Abdaal credited the book on the same podcast as a transformative discovery that reshaped his productivity mindset and business goals. Additionally, Robert Greene shared on The Daily Stoic that he frequently reads his friend's work, naming it his absolute favorite among them.
Who recommended it
- Ryan Holiday Recommended
- Garland Robinette Recommended
- Chris Williamson Recommended
- Ali Abdaal Recommended
- Troy Baker Recommended
- Buzz Williams Discussed
- Patrick Dempsey Recommended
- Guy Raz Recommended
- Brooke Wells Recommended
- Chase Koch Recommended
- Billy Bush Recommended
- Billy Oppenheimer Discussed
- Molly Young Discussed
- Nate Boyer Discussed
- Greg Harden Discussed
- Dean Rickles Discussed
- Stefi Cohen Recommended
- H. R. McMaster Discussed
- Camila Cabello Discussed
- James Smith Recommended
Ryan Holiday — 5 mentions
“So when the obstacles away came out, it it did okay, but it didn't hit the list. It should have and it didn't.”
“I read them all the time—Obstacle is my favorite, Ego is the Enemy, but they're all really great.”
“What had happened is the Patriots–someone at the Patriots had read The Obstacle Is The Way. And then obviously there was that devastating loss and then he had recommended the book to someone in Seattle; actually, to John Schneider who then read it.”
“and then I wrote the proposal for the obstacles away there and I sent it to them the week that trust me online came out”
“I think one of the benefits for me when I was thinking about writing The Obstacle Is the Way, and I've talked about this before, is that my publisher offered me half what I got for my first book for what was supposed to be my second book.”
Garland Robinette — 5 mentions
“I wrote 'Trust Me, I'm Lying' in New Orleans, and then I wrote the proposal for 'The Obstacle is the Way' and I sent it to them the week that 'Trust Me, I'm Lying' came out.”
“um what what gives it I can't remember bear with me um the optical is the way yeah he wrote it I lived it”
“As I showed my wife last night, I said that, um, uh, what gives it I can't remember; bear with me, um, the obstacle is the way; yeah, he wrote it, I lived it, yeah, that is if anybody could read any book, that's it.”
“it it it just it again that book not because you wrote it I gave it to my daughter and I said the minute you get comfortable and a little boarded at work think about another job think about disrupting your life even if you [ __ ] up”
“yeah you know I'm sure he is the way yeah that that ought to be a serious because it's it's really critical thinking should be the way”
Chris Williamson — 3 mentions
“Other stuff I did that really helped, I read The Obstacle is the Way by Ryan Holiday. I read The Art of Resilience by Ross Edgely, and I watched uh Resurfaced, which is a Amazon Prime documentary about Andy Murray's hip replacement.”
“obstacle is the way by Ryan holiday and watch the documentary resurfaced with Andy Murray”
“obstacle is the way by Ryan holiday art of resilience by yourself on Audible”
Ali Abdaal — 3 mentions
“ever since I discovered the obstacle the way and I realized that my 10year goal for the business is to be profitable while helping people”
“Honestly, I was thinking about that and all the Stoic stuff I've been digesting since I discovered 'The Obstacle is the Way'.”
“Honestly, I was thinking about that and all the stoicism-type stuff that I've been drinking the Kool-Aid off ever since I discovered The Obstacle Is the Way.”
Troy Baker — 3 mentions
“because the first one that I read obstacle was the way it was the first one that I read but I I say red it was it was done as a uh as an audiobook”
“And I think you even talked about this in, because the first one that I read, The Obstacle is the Way, it was the first one that I read.”
“and then that led me into uh the obstacle is the way”
Buzz Williams — 2 mentions
“I said to my guy, 'Hey, why haven't I got Ryan's book? Can you look up when I ordered it, coach?','I ordered it on this day.”
“whether that's the success that came from the obstacle is the way book yeah versus it's time to write the next one”
Patrick Dempsey — 2 mentions
“and my technique was like you know the obstacle is the way right so very much the same way”
“I added an acting thing; I did a 10-year anniversary edition of ‘The Obstacle is the Way,’ and it hasn't come out yet. But a lot of athletes, like I work with the US ski team, use it because they always deal with last-minute challenges like equipment failure, weather problems, and delays.”
Guy Raz — 2 mentions
“And there's actually a book about this called The Obstacle Is the Way.”
“I wouldn't say that comes naturally to me, but it is something that I am working on. There's actually a book about this called 'The Obstacle Is the Way.' And it's great because the obstacle has been the way tonight.”
Brooke Wells — 2 mentions
“And then I read, "Your Obstacles Away." That was a really good one. Let's see, "Atomic Habits."”
“and then i read your obstacles away that was a really good one”
Chase Koch — 1 mention
“I read all the stoic philosophy. I’m a big fan of Ryan Holiday. One of the books that had a huge influence on me was The Obstacle Is the Way.”
Billy Bush — 1 mention
“there's a great um book that my friend Ryan holiday with whom I came became friends during this process but holiday wrote this book called The obstacle is the way and this obstacle this terrible thing in your life that you're trying to avoid and run away from”
Billy Oppenheimer — 1 mention
“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?”
Molly Young — 1 mention
“so for example Ryan holiday who the big breakthrough book in 2014 he wrote the obstacle is the way and then subsequently wrote The Daily stoic and he's written a bunch of books about the philosophy”
Nate Boyer — 1 mention
“someone at the Patriots had read the obstacles of the way and then obviously there was that devastating loss”
Greg Harden — 1 mention
“I'll love any book where uh Tom Brady says the title of one of my books”
Dean Rickles — 1 mention
“this guy you had Ryan holiday he's the guy that did that obstacle book right Obstacles the way is that the guy”
Stefi Cohen — 1 mention
“and that's why your bug the obstacle is the way it was wanna honestly i i keep telling you about it was one of the most influential books that i've ever read”
H. R. McMaster — 1 mention
“so so uh uh shake talk noon who's a friend of mine and we worked together on a number of initiatives in the middle east and beyond uh we he's he's an author himself he's very intellectually curious and he said hey i just i just read this great book called the obstacles the way and i and i'm going”
Camila Cabello — 1 mention
“when i saw like a couple months ago i was i was like you know i read ego i read obstacles the way like i think like two years ago”
James Smith — 1 mention
“that is the meaning that struggle is the meaning the obstacle is the way you know like that's that's what that's how it works”
Mentioned on the show without a named speaker — 1
“Your friend Ryan Holiday has an intriguing post where he shared his top 25 biography recommendations; the introduction emphasizes how successful individuals all have biographies on their shelves.”
Also mentioned in the same episodes
- Meditations
- The Daily Stoic
- Ego Is the Enemy
- Discipline Is Destiny
- Stillness Is the Key
- The Art of Resilience
Other mentions (82: passing, ad reads, own books)
“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.”
“She had just read my book, The Obstacles Away, if I would fly out to Maui to talk about it for this episode she was doing.”
“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 phosphorescence in I I'm doing a 10 year anniversary edition of the obstacles away and I use one of your stories in it”
“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”
“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.”
“And so yeah, when I was writing The Obstacle Is the Way, it was hey, let me tell you about this thing called stoicism.”
“originally The Obstacle Is the Way was in the business category.”
“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.”
“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 we got connected by someone and he said, "Oh, I've read your 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.”
“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.”
“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.”
“like 90% of the talks I give are still about the obstacle is way a book I wrote 10 years ago so I can just wake up every day and just collect dividends from a thing I already did”
“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.”
“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.”
“so my favorite for Marcus which I actually remember thinking about when the obstacles the way came out”
“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.'”
“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.”
“There's a story I tell in 'The Obstacle is the Way' about Phil Jackson.”
“There's a story I tell him the obstacles way about Phil Jackson”
“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.”
“like I reread I reread the obstacles way to my son at some point during the dnic”
“But like I reread the obstacles away to my son at some point during the editing; he wanted to like read something I'd written, and so I read it to him, and I was like, this is fast; like I was like this is so short and tight and fast.”
“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 uh 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 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.”
“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”
“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'?”
“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”
“the obstacle is the way so this this is from from what I read about it this this statues from 1840”