in: Advice, Character, Podcast

• Last updated: September 27, 2021

Art of Manliness Podcast #65: The Obstacle Is the Way With Ryan Holiday

In this episode I talk to Ryan Holiday, author of the soon-to-be-released book The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph.

Show Highlights

  • Why great men from history were drawn to the philosophy of Stoicism
  • The 3 principles necessary for turning adversity into opportunities
  • The difference between persistence and perseverance
  • And much more!

Book cover, the obstacle in the way by Ryan Holiday.

I highly recommend picking up a copy of The Obstacle Is the Way. I’ve already read it twice and it will likely be one of those books I re-read each year. It’s a quick read but filled with powerful information.

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Read the Transcript

Brett McKay: Brett here and welcome to another edition of The Art of Manliness Podcast. Well, a common thing that we have on the podcast and on the website is this idea of overcoming adversity. Our goal is to help men become resilient in the face adversity and you know whatever challenges you might have, whether it’s economic or physical or emotional or mental, we want to help you overcome that so you can achieve the goal that you have for yourself and this whole idea of overcoming adversity or being resilient in the face adversity has been a concerned for philosophers and great men through history for eons. And a group of man that really took this matter to heart were the Stoic philosophers of ancient Greece and Rome, where they developed the whole philosophy and ethic on how to remain calm and in control even when things are just going haywire around you. The Stoic philosophy has been popular amongst just great men from history, the founding fathers, many of them were students of Stoic philosophy, military generals have been students of Stoic philosophy. Anyways, I am a big fan of Stoicism. Our guest today has been student of Stoicism, he has written about it and he’s taken Stoicism, used as a lens to look at the lives of great men and women to see how they applied Stoic principles to turn adversity into opportunities. His name is Ryan Holiday and his book is the Obstacle is the Way: The Timeless Art of Turning Trials into Triumph. Today, Ryan and I are going to talk about Stoicism. We’re going to talk about the three principles that he lays out on turning obstacles into opportunities. We’re also going to discuss great men and women from history who overcame insurmountable odds to great things and actually used that challenge as a catapult to do amazing things. And we’re going to talk about how you can apply this into your own life. It’s a fantastic podcast, it’s a fantastic discussion, I think you’re going to get a lot of it, I did so stay tuned.

Ryan Holiday welcome to the show.

Ryan: Thanks for having me.

Brett McKay: Alright, so your book is The Obstacle is the Way; where did that come from, can you explain that?

Ryan: Yes. So… I mean there is a Zen saying ‘The Obstacle is the Path’ right, which I heard before and for me as I ––so the book is written and based in the Roman philosophy of Stoicism and there is a quote from Marcus Aurelius where he says, you know, “The impediment to action advances action. What stands in the way becomes the way.” I’ve seen in a different translation where he said ‘The Obstacle Becomes the Way’ and it’s sort of it was at this moment when I realized that like Eastern and Western Philosophy were both saying the exact same thing, which to me means some sort of internal truth, right and so I really like that phrase, it really stuck with me. I think I’m actually going to get it tattooed on my arm this weekend but the idea was the things that we think are holding us back or every time we think there is some problem, it’s actually like an opportunity to do something, something different but it’s an opportunity to make things better, right. And so I wanted the whole book is based around that idea and still with examples and stories of people who actually did that and I just found that like that phrase so clearly articulates a timeless idea that I think all the people you talk about manliness, all the people that I’ve, you know like admire in the course of my life and in the books that I’ve read that’s the one similarity that they seem to have in common, that attitude.

Brett McKay: Yeah, and that’s ––I mean the book, it’s about Stoicism but you don’t kind of focus on like the history of it like… you know there’s lots of books out there like that right.

Ryan: Sure.

Brett McKay: You kind of focus on actual concrete examples of people living today or in the recent past and what I find fascinating you kind of have–– you devote a section to these all these great men and great people from history like they’re drawn to Stoicism, like they read the Stoic all the time, what is about Stoicism that draws these sort of great souls to the philosophy?

Ryan: Well, I think it goes down to ––and yes, you go to a point, I don’t think anyone wakes up in the morning and things like, ‘Oh, I need more philosophy in my life,’ because philosophy seems like an abstract, theoretical, or college course that doesn’t actually help you with your problems. And I think what sets Stoicism apart from that and this goes to your question is–– it was actually written by people who do things or who did things like Aristotle is very smart but like he was an academic right, that’s what he did. He was a smart guy who wrote about the world but it was inherently limited by the fact that he just wrote about the world rather than living it right. He was Alexander’s academic advisor and teacher but he wasn’t out like leading the troops with Alexander, right.

Brett McKay: Yeah.

Ryan: But the difference between Aristotle and Marcus Aurelius and Seneca is that these were men who lived very trying difficult lives on sort of on the battle field both literally and figuratively and so the philosophy is rooted in action, you know Marcus Aurelius is the most powerful man in the world, Seneca is an influential businessman and advisor to powerful politicians, Epictetus although a teacher who did freed slaves so these weren’t theoretical explanations about how the world works or this was really in the school of like sort of practicality and so I think the reason that philosophy has spread so long is that it’s written by doers for doers. And then, yeah, I’ve run through some of the people who like the stoics, yeah, Ambrose Bierce was a civil war veteran and an contemporary of Mark Twain. You know you have James Stockdale who’s spent you know as a fighter pilot who spent seven-and-a-half years in Vietnam prison camps, Frederick the Great, you’ve Theodore Roosevelt, you’ve George Washington, Thomas Jefferson, and a copy of the letters that I picked as, the essays that I’ve picked up this on his bedside table when he died. You know, Stoicism was written at a very tumultuous time in history and when you look at other tumultuous times in history you tend to see it pop backup and find a new audience because of who it’s meant for and what it talks about.

Brett McKay: Yeah, that’s a great point. I just finished reading a book called Roman Honor written by–– I forgot the name of the professor–– anyways, she kind of talks about history of Roman Honor, right, like honor is like it’s your reputation, right.

Ryan: Right.

Brett McKay: And it’s like you care about what other people think about you. And she makes the argument that Stoicism can to rise in the Roman Republic as the republic was declining, so people had like you know Marcus Aurelius, like they stop kind of caring what other people thought about them and just were more concerned about survival.

Ryan: Right.

Brett McKay: And it’s interesting that we kind of you’re right like today we see Stoicism on the rise, it seems like a lot of entrepreneurs are really into it, I don’t know what is about today’s climate that makes Stoicism so appealing again.

Ryan: Sure. Well, I think that, of course, Stoicism is rooted on the idea that you don’t control the world around you, you only control yourself, right and it doesn’t matter what other people are doing, it doesn’t matter what they can do to you, it just matters how you respond to that. And so, I think, one of that ––you know, that’s the attitude you needed in the decline and fall of the Roman Empire, that’s the attitude you needed during the American revolution, you needed during Civil War, you needed during Victorian Era, it’s you needed during the Industrial Revolution, you needed in a prison camp and then today you needed in you know a time of economic upheaval and shifts and you needed in a world where you don’t want entrepreneurs but people who are solely responsible for themselves and for other people, right. Like when you’re an employee the idea of Stoicism is perhaps less attractive because the ideas of discipline and self-control and… they’re not as important, right because someone is taking “care of you” and you know if you’re starting a company from nothing, it’s a high stress, it’s temptation driven, a distraction driven environment where if you’re not on your game and you not holding yourself to some sort of standard and you don’t have framework for dealing with the problems that you’re going to face, you’re not going to last very long as an entrepreneur.

Brett McKay: Alright, so in The Obstacle is the Way, you kind of just do Stoicism down to like three principles.

Ryan: Sure.

Brett McKay: What’re they ––and I guess there’s a whole bunch of follow-up questions we’re going to ask, but sort of what are the three kind of distinct principles of The Obstacle is the Way?

Ryan: Yeah. So, I think Stoicism is a bunch of different principles or disciplines, right and I’m focusing on this one idea of using Stoicism to turn obstacles upside down. Like the Stoic thinking is nothing bad that can happen to you because everything is an opportunity to practice some virtue and they’ve pretty expansive definition of virtue, but in every opportunity even if I was trying to one thing and that’s impossible, I can still all these other things and so the three disciplines that I think are really important to that idea. The first step is perception and that’s you know being able to control your emotions, that’s being able to look at things objectively, that’s being able to sort of shift your perspective so you can see things from various angles and that’s having a sort of a strong nerves and you know freaked out by something that’s hard or difficult, that’s having a kind of ambition or goal so you’re able to see past what other people say, you know, isn’t realistic. So, those perceptions are really important and I think the clearest iteration or explanation of that idea is a quote from Epictetus. There is no good or bad, there is only perception, right. Things are what they are we decide whether they’re good or bad. And if we don’t decide they’re bad then they’re good and we don’t decide they’re good they’re bad. And so if you can look at these things and prove that in yourself from adding these labels and explanations your obstacle is going to be much easier, right. The next one is action and I perhaps took more liberty with the action phase I did anywhere else, but you know the Stoics were sort of ruled by what they felt like sort of virtue and so that’s you know thinking of people other than yourself that’s you know being just and honorable as you said. So, I’m thinking about how you use those approaches to solve problems. I think energy is probably the biggest, you know people face these problems and they sit around and look for these like perfect solutions to them, right. It’s like oh, I need this, I need that or like I told history in the book of Amelia Earhart and I may have gotten this example from you. By the way, her first offer to fly across the Atlantic was preposterous offer, right. It’s like one of the first female who fly across the Atlantic but we’re going to say two male chaperones with you, they’re going to get paid, you’re not. You’re going to be cramped in the back of the plane, you’re probably going to die and there are going to get most of the attention after. And like to me that’s very analogous to ––I’m sure a lot of people that you know who graduated from college recently and then they moved back in with their parents because they didn’t get the perfect job offer that they felt that they’re entitled to do, right. That’s not what Stoic does. Stoic takes what they were given as a given and works on it from there. So I think the action section is very much about you know creativity, it’s about pragmatism, it’s about persistence, there is a military strategy in there where I talked about you know attacking from the flanks rather than head on, not having strength go against strength. And then final one is the discipline of the will. Now, I used Abraham Lincoln as the example of this guy who is a sort of plotting, enduring patient man who is able to outlast this terrible thing that was the Civil War because he’d suffered from depression his whole life and he is sort of he knew his favorite saying was this idea of this too shall pass and so that last section is about the understanding that there are some things that you can’t change in life and you’ve got to accept them and you’ve got to outlast them or find benefit within them.

Brett McKay: You sort of talked about it so far but this idea that sort of underlies these three principles is like inversion, right always flipping things. I think we can see that in the perception thing, you want to like we got an obstacle and you want to flip it and say there is an opportunity there. But it also seems like it underlies these other two principles like in action and in will, am I right in that or….

Ryan: Yeah, totally. I mean look I think a clear example of this is–– if you look back on your own life or if anyone looks back in their own life, they see failures that were really awful at that time but with distance they almost wouldn’t trade those failure for anything because we learn from them, we got stronger from that. We look at bad things that happened to us and we realized how often they’re blessings in disguise, right. And yeah, so we know failure has benefits for us and yeah we do everything we can to avoid ever failing right or we fail sort of kicking and screaming and so …one of the things I’m talking about is more irritative approach instead of trying to perfect everything in the lab, which is what you’re thinking you need to do to be perfect and prevent bad things whatever happening. In fact, you want to be more fluent and iterative, so you’re failing on purpose and you’re learning from them. So it’s like how can you take the worst things in life, whether it is failure and find an advantage of it. I have a chapter and they’re on sort of meditating on your own mortality and your death is obviously the worst thing that can happen to us, but without death life is meaningless. It just goes on and on and there is no sense of urgency, there is no sense of purpose, there is no… if life goes on it means the bad things in life go on and on as well. And so I think if you can look at death and you can find a motivating, a beneficial factor from it, it’s pretty clear to me that you can find good things in pretty much every aspect of what you’re doing.

Brett McKay: Yeah, and one thing that really struck to me in your section about action, talking about attacking from the flank right. Usually the people want to like–– you’re going to attack, you got to just like.. you got to move, you got to be the aggressor.

Ryan: Right.

Brett McKay: That’s what action means. But you make an argument, devote a section you’re like no, sometimes that’s not what you want to do. In fact, you want to just be passive and let them come to you, so you’re like inverting the action.

Ryan: Yeah, so like one of my favorite writers is B. H. Liddell Hart. He was a brilliant World War I commander who became a military strategist. He wrote a bunch of excellent books but he did a study of basically ––I think he looked at about 250 campaigns throughout history and he was like what was the decisive battle in all of them, right. And in almost everyone, it was not a hand-to-hand confrontation between two major armies. It’s not a Napoleonic clash between two major you know entrenched forces. It was always something around the side or just section or a quick maneuver that caught someone off guard, right. Like the decisive battle of the Revolutionary War was you know George Washington crossing the Delaware on Christmas Day to attack troops that might have been drunk, right. And, yeah, when we ––like if you’re starting ––if someone else wanted to start a site about manliness that’s probably not a good idea. If you want the male demographic, don’t start another site where you’ve an entrenched competitor who owns a net, right.

Brett McKay: Sure.

Ryan: You want to find the areas where the strong are weak and you’re strong and that’s what you did it, that’s where you attack like force doesn’t so against force. And when you look at some of the most powerful effective movements in history whether it’s Civil Rights Movement, whether it’s Gandhi or militarily it’s the Russian versus Napoleon and then against the Germans, they just retrieved into the interior and they let this main army sort of dissipate all it’s energy until they realized that they walked into a trap, right.

Brett McKay: Yeah.

Ryan: And so that idea of passive resistance or almost Ju-Jitsu move I think is highly underrated and it’s underrated and underutilized because it’s not as exciting and it doesn’t feel as manly, but if works it works, right.

Brett McKay: Yeah, exactly and it’s pragmatic like the Stoics you talked about, yeah, if it works that’s what we’re going to do.

Ryan: Truly.

Brett McKay: Right. So, yeah, one thing I love about this book is you just–– there is so many––you go to history and you find examples, like concrete examples of what these principles applied, I mean I love that and so we’re doing on The Art Of Manliness, we try to do. Was there a particular instance or example that really called out to you personally?

Ryan: Yeah, so… and that’s what I’m trying to do is I don’t want to just tell people that this stuff is good. I want to like show examples and I learned this from Robert Green who write the 48 Laws of Power. He was my mentor and he sort of showed me as a best way to tell to make a point to tell it in the story, so that’s what I wanted to do. You can just read the original books if you want the theory, if you want examples like that’s why I wrote this book. Two favorites, one of my favorites I actually got from people I don’t know I call Brett when I was thinking about writing this book and I was like you know who are your favorite people in history that overcame obstacles that I should look and ironically he gave me a female example, gave me Laura Ingells Wilder who you know you think of as this you know like she wrote this books about the prairie but she lived the life that she is talking about in the book and if you look at on paper that way was terrible right, like backwoods of Florida than like the prairies of Kansas, you know like a grass hut, like that would be awful right, but she loved it, like she saw this as an adventure. And I’ve a quote from her in the book where she says there is good in everything if you look for it, which is actually very Stoic idea. Shakespeare has a similar line where he says nothing good or bad– but thinking makes it so. And so idea of this little woman, like which I guess is funny but this little woman, this little woman just seeing all this adversity as an adventure and that switch turning it from awful to amazing and that’s why it’s enthralled all these you know kids or readers for 100 years now, I think is really great and I love that story. Two of my favorites, you know I tell a story of the Athenian Order who a lot of people didn’t know before he came this powerful you know speaker who could mobilize the Athenian Army against Philip of Macedon was a cripple boy with a stutter whose parents died and then his guardian saw everything from him and he––it’s almost like a movie montage like he overcame his stutter by like filling his mouth with rocks and then talking through them or and shouting through the wind until he developed his strong lungs. And then at one point built an underground study and shaved his head, half of his head so he’d be too embarrassed to go outside and so it’s like, you know this terrible thing happened to him, he was you know, his trust was violated as a child, he was born disabled and yet it was precisely those events that made him who he ultimately was and it was in the course of writing those wrongs that he developed his reputation as a speaker and he eventually became a politician and has great influential figure. So I really like Ulysses S. Grant, this is just great and I think is criminally underrated in history as a thinker or strategist and a man. He wasn’t a great president but whatever, John D. Rockefeller is one of my favorites, Amelia Earhart was great, and then Irwin Romo, I think is always a controversial figure but was really interesting and fascinating as a strategist.

Brett McKay: Yeah, those were all good example, there’s so much you can learn from those people.

Ryan: Was there one you like?

Brett McKay: Well, you know, of course I love Teddy Roosevelt.

Ryan: Me too.

Brett McKay: And I love the Demostotes that was, I mean his story is just fascinating and then who was the other one that I–– you know the Hurricane right, that was a great one and I think it’s a perfect example of living in like The Obstacles is the Way, like you just decided I’m not going to be a prisoner, I might be in prison but I’m not–– you’re not going to treat me as a prisoner.

Ryan: So, I just read this as an amazing article I forget about which boxer but I guess there was another boxer at the same time, who actually box in prison and almost won heavy weight title.

Brett McKay: Wow.

Ryan: It was–– I think was on Bleacher Report, it was just crazy long read about this guy who like would fight in the–– they would bring boxers and set like you know how you’re allowed to have job in prison, right.

Brett McKay: Yeah.

Ryan: To let him his job be a boxing coach and he almost won the middle weight like belt as a professional boxer in the prison and so to me like this story is just good, chances are you and I will not be wrongfully accused of quadruple homicide like him right, if all goes as plan that won’t happen, but at the same time it surely wasn’t Hurricane Carter’s plan either right, but like if they can weigh out you know a 20-year prison sentence and somehow come out not just not worse off but better off, I’m pretty sure like you know your deadline getting moved up or you getting laid off from a job or you know the economy thinking, these are not nearly as catastrophic events as we’re telling ourselves right now because that’s how they feel.

Brett McKay: Yeah, here is a question I have as I was reading this, you read these examples from history and like the obstacles these people face, right they’re like tough stuff like war, famine, death, harsh weather whatever, property and like it’s sort of encounter intuitive like I’ve encountered like physically hard things in my life…

Ryan: Sure…

Brett McKay: And tragedies in my life. But for some weird reason like it was hard but it seemed easier to overcome than like some of those intangible and internal problems in your head.

Ryan: Sure.

Brett McKay: Do you agree with that and if so, why do you think that is? Like why it is easier to like confront like you know a physical challenge or a tragedy than it is sort of like the daily grind of life?

Ryan: Sure, well, I wonder if part of it is like biologically were like designed, it’s more imperative that we survive those than the other problems, right. Like your genes don’t care if you’re happy as much as they care that you just don’t die, you know what I mean.

Brett McKay: Yeah, yeah.

Ryan: That’s part of it. And then I think–– one of the things that I realized in the book is that you look at these terrible things that these people went through and like sometimes it wasn’t like the worse thing that ever went through right, like and you realizes because they’ve this kind of frame––well, they are framework for dealing with obstacles than I think Stoicism has been part of that but when the world felt much more unpredictable and capricious than it does now. It was easier to take these things and strife you know and like when tornado could come and you didn’t know what a tornado was and you just thought the hand of god was turning your town upside and down, right. You’ll be a little less conceded and pretentious and delusional about how safe you were in a given moment. When like your wife unexpectedly dies and you didn’t know it was because the cut on the finger got like infected, you would be more humble about you know tempting faith and taking things for granted, I would say. And but I also wonder if just being consumed by that fear and doubt made some of the emotional problems taking a back seat and so now having dealt with some of that stuff, we feel more insulated and yet we don’t have that that framework that they did to deal with tough problems and I think we need that. And I also, the final thing that would say is like I don’t want to discount anyone emotional or difficult problems like you know your girlfriend dumps you, it can literally feel like the world is ending and it feels really awful and that’s tough and I don’t want people to say like to pretend that you don’t feel pain and that is not bad because they, like it’s certainly better than being like stumped on by an elephant.

Brett McKay: Yeah, that’s a good point about how we–– you know we live a time of relative like it’s the safest time in human history, right.

Ryan: Right.

Brett McKay: But yet we still think it’s the most dangerous time like oh, it’s horrible out there and I guess this is because there are so few instances of like crime, violence, or mayhem, but it does happen it just like holy cow, this is the worst, worse ever been, that stuff happened all the time.

Ryan: Sure. I mean look you and I are talking to each other on high definition video, states apart from each other for free.

Brett McKay: Yeah.

Ryan: Right, like this is crazy and you’re recording it and it’s going on website and will be seen by millions of people like, it’s very easy when those things are common place in your life, just start to assume that like the world has been tames or domesticated and all sharp edges had been rounded off. And ironically this is what the Stoics talked about that makes the bad things feel so much worse because you’re never anticipating them, so I talked a lot about that like we would be much better off if you thought about the worse case scenario more often.

Brett McKay: Yeah.

Ryan: And I’m not saying that you should be a pessimist but if you’re not anticipating and there is a the idea of premeditation of evils, like what could go wrong, this is what I’m planning, but I understand that X, Y, or Z could happen and this is what I planned to do about them, prepares you and does the surprise and the shock in a much beneficial way.

Brett McKay: Yeah, I think it’s interesting too that–– okay, so you know the Romans, the Stoics like yeah, they any face, like it was a horrible time then, but like what I found interesting is like the people who were drawn to it were like successful people.

Ryan: Right.

Brett McKay: People who could relative to this probably sheltered from a lot of that stuff and it seems like they were drawn to it as a way to.. I don’t know hurting themselves up.

Ryan: No, I think that’s great insight and what a lot of people missed is they think that Stoicism, because we read these exercises and they hear it like oh, you should think about the worst thing that should happen and you should prepare for poverty and warfare and they think that it’s depressing, right and that these must have been just really down people and in fact no, and sort of like–– it’s almost like a bias by omission that’s been wrongly introduced by one of the readers. Nobody needs help like what Stoics believe was nobody needs help like being reminded, like what happiness feels like and why you should smile when to love your children and like having sex and like you don’t need a book that like tells you these things are good, right, that’s natural, like feeling good when you’re successful that sort of biologically takes care of itself. But what the Stoics felt is like what we need is that, we need that counter balance, we need reminder so we don’t get too exhilarate in either direction or too extreme and these were reminders just sort of center themselves. It wasn’t like depressing people telling themselves depressing things, it was normal people guarding themselves and preparing themselves for things that they hoped wouldn’t happen, but they knew very well could happen.

Brett McKay: Yeah, yeah, it’s, it’s really fascinating. So when I was reading the book the one––I mean all of it is really great, but then one section that hit home to me for some reason was in your section about the will…

Ryan: Yeah.

Brett McKay: And about perseverance and I feel like all of us have this tendency to believe that everything if you know ––we’re waiting for things to be just right. Like we’re waiting for Plato’s republic right and instead you know how do you overcome that because I know it’s not true, right, I keep on thinking okay, if everything was just this way then my life will be awesome, but never ––I mean you have kids man like nothing goes as plan, so how do we overcome this tendency to believe that my life will be great if things are just so?

Ryan: Sure. Well, I sort of–– I make the distinction in the book. In action I talked about persistence, which is just sort of staying at and hammering away …

Brett McKay: Yeah.

Ryan: And then persistence––sorry, perseverance I say sort of something deeper and larger, that’s like that deep endurance like you know you’ve to be persistent to train yourself to run like five miles, but if you want to do like an ultra marathon, like you’ve to had this deep iron part of you that you can rely on when things are awful and you just want to quit. And so like–– I’m not sure if there is like a recipe other than like you just have to do develop the skill overtime, you know and you have to realize that like things cannot go the way that you wanted and things can be bad and people can prevent you from doing what you want, but they can never prevent you from holding on, right. Like you can get rejected by every, you know, record label in the world, but it’s ultimately up to you when you decides to quit music you know, like I can put out this book and it can sell zero copies but it’s ultimately up to me, I make the final decision on whether this is like a failure that I quit. Like no can ever take the ability to preserve away from you other than death, right and that’s what I think, that’s what these people had. Like I quote there is a line about Magellan and someone was like what was his greatest skill and his greatest skill was that he could endure hunger better than the other men, like he just had a little bit extra in the tank and he wanted it worse than them, or wanted it more than them and he just would not give up and he would endure whatever it took to get there. And I think that’s really important and I also think that’s the opposite of what a lot of us are taught and a lot of us don’t develop that skill. You know like we talked about Theodore Roosevelt like he was born with asthma, I remember kids of my age having asthma and it’s like they can’t play sports, they can’t do this and their life was defined by what they can’t.

Brett McKay: Yeah.

Ryan: Rather than like … rather than being someone like Theodore Roosevelt who was like–– who always took that as a challenge and I think the book is about seeing those things as a challenge rather than a constraint.

Brett McKay: Yeah. Well, are there any examples from your own life where you turned an obstacle into an opportunity?

Ryan: Yeah, so that’s the one question I probably get the most whenever we’re doing stuff for this book and in weird way and I know it probably sounds like I’m dancing around, I kind of like say like that question.

Brett McKay: Yeah.

Ryan: Because like this isn’t about me, right.

Brett McKay: Yeah.

Ryan: Like framework for overcoming obstacles that yes, I personally used and took a lot out of, but I also like I wrote the book for myself, right like I wrote the book so I could get better out of it, I’m not in the book at all, I’m not talking about myself in the book.

Brett McKay: No, yeah.

Ryan: But I’m talking about like this is what works and we can always use it. But like you know we all go through stuff in our lives, like you know I dropped out of college in my teen, you know my life have been high stakes, high pressure for as long as I can remember and everyday there has been problems and things that make me want to quit or make me want to stop and I’ve to remind myself that these are challenges that are you making me better, these are opportunities to stuff like I’m in the middle of something now with some of my business partners and it’s like, it’s awful and then it’s like–– but it is also forcing me to have confrontations or conversations that I would not rather have then I’m getting better from and I’m learning from and I’m figuring out. I’m figuring out what I don’t want like from this exact experience and I think it’s that attitude that’s helped me you know achieve what I’ve achieved but I would much prefer to put the spotlight on other more relatable challenges because I don’t want to–– I don’t want to talk to someone who has had over–– who is born into you know abject poverty and say like look like I know what you’re going through, because like you know my first world problems were really tough to get through.

Brett McKay: Well, it’s interesting that you said you wrote this book for yourself, it sounds like very much like Marcus Aurelius, you know, meditations, like we read them but like that was like for him only, really.

Ryan: Totally, yeah, like most of the Stoic works like they were works for publication, they were like Stoicism is series of exercising and turning any obstacle upside down is an exercise and they would write examples or anecdotes or new phrasing to help them like be better at. And for me I was trying to write the book like I’m a writer so I write things, so a little bit different, but I was trying, I was thinking about myself when I was writing the stuff and thinking about the times that I did the opposite of the stuff and what I wish I’d done and what I want to do next time.

Brett McKay: Yeah, that’s awesome. Is there is something like ––I always like to end the podcast with like, you know…

Ryan: Sure.

Brett McKay: Sort of like a take away, like what can I do now or and action point like is there one thing that you think a person who is listening to podcast right now, can do today, that they’ll b there experience like payoff right, you know like man, that’s… this is helping me from The Obstacles is the Way.

Ryan: Sure, I guess I would ––I think this mental flip is really easy to apply. It’s not easy to do and live like, but it’s easy to think about. It’s like take the worse things that ever happened to you and then think about the benefits that you derive from that. You know like getting rejected from this, getting kicked out of that, you know quitting this and then think about what happened after and I think you’ll see that it wasn’t all bad, that there are real benefits. And then instead of waiting 5 years or 10 years or 20 years afterwards to get those benefits, why don’t you start thinking about them now. So, whatever that thing that you’re afraid of or this thing that’s front of you are facing you know like what can you–– what benefits are inherent within it and can you focus and lean into those and does that make you know the pills, so to of speak, easier to swallow.

Brett McKay: Yeah, that’s great stuff and I think that’ll really help out a lot and I love too about your book and what you’re putting out here is that–– yeah, it’s easy to think about, but it’s hard to put in practice, but I love that. It’s like a challenge that it’s like, it’s not going to happen right away, it’s sort of a lifelong process.

Ryan: Sure. And look I also think like when I wrote this book to convey like wisdom that a lot of people smarter than me had put on paper or in history over the years, but like I also just want to remind people look whatever you’re going through, chances are 100 years ago someone went through more or less the same thing but it probably works, right, like you know your money is tight like, but you know at least those prisons don’t exist.

Brett McKay: Yeah.

Ryan: yeah, like things were much worse before and this is a great time. But for those people, many of them wrote about what they went through and gave very exclusive advice and lessons. You know there is a great line from Bismarck, I think, where he is saying like you know any fool can learn from experience, I preferred to learn from other people’s experiences.

Brett McKay: Yeah.

Ryan: Like there is a bibliography on this book, you know I’ve my reading list where I give out recommendations like but there is so many books out there people giving amazing advice on dealing with tough, crappy problems, like benefit from my knowledge don’t do it by yourself and why knuckle it when you don’t have to.

Brett McKay: Yeah, that’s awesome. Well, Ryan where can people find out about The Obstacles is the Way?

Ryan: Yeah, so theobstaclestheway dot net or dot com, I think, is the website. My website is The book is available in the bookstores everywhere. It’s on Amazon, check it out, I hope you really like and I always take emails from people who have questions. It’s just my name and at gmail.

Brett McKay: Awesome. Well, Ryan Holiday, thank you very much. It’s been a pleasure.

Ryan: Thanks for having me, man.

Brett McKay: Our guest today was Ryan Holiday. Ryan is the author of the book The Obstacle Is The Way: The Timeless Art of Turning Adversity into Advantage. The book is releasing on May 1st, you can find that on You can also find information about his book at I highly recommend you pick a copy, it’s quick read but it’s just packed with information. I’ve read it twice already, I’ll probably reading again pretty soon because it’s so–– it’s just got so much great, useful and inspirational information, so go check it out.

Well that wraps up another edition of The Art of Manliness Podcast. For more manly tips and advice, make sure to check out at The Art of Manliness website at and until next time stay manly…

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