#65： The Obstacle Is The Way With Ryan Holiday
Episode Stats
Summary
In this episode of the Art of Manliness podcast, Brett and Ryan Holiday talk about the Stoic philosophy of Stoicism and how it can be applied in your life to turn obstacles into opportunities. Ryan Holiday is the author of The Obstacle is the Way: A Timeless Art of Turning Trials into Triumph.
Transcript
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Brett McKay here and welcome to another edition of the Art of Manliness podcast. Well, a common
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thing that we have on the podcast and on the website is this idea of overcoming adversity.
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Our goal is to help men become resilient in the face of adversity and, you know, whatever challenges
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you might have, whether it's economic or physical or emotional or mental, we want to help you overcome
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that so you can achieve the goals that you have for yourself. And this whole idea of overcoming
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adversity or being resilient in the face of adversity has been a concern for philosophers and great men
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through history for eons. And a group of men that really took this matter to heart were the Stoic
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philosophers of ancient Greece and Rome, where they developed the whole philosophy and ethic on how to
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remain calm and in control, even when things are just going to pot around you. The Stoic philosophy
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has been popular amongst just great men from history, founding fathers. Many of them were
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students of Stoic philosophy. Generals have been students of Stoic philosophy. Anyways, I'm a big fan
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of Stoicism. Our guest today has been a student of Stoicism. He's written about it and he's taken
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Stoicism, used it as a lens to look at the lives of great men and women to see how they applied Stoic
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principles to turn adversity into opportunities. His name is Ryan Holiday, and his book is The Obstacle
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is the Way, The Timeless Art of Turning Trials into Triumph. Today, Ryan and I are going to talk about
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Stoicism. We're going to talk about the three principles that he lays out on turning obstacles
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into opportunities. We're also going to discuss great men and women from history who overcame
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insurmountable odds to do great things and actually use that challenge as a catapult to do amazing
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things. And we're going to talk about how you can apply this into your own life. It's a fantastic
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podcast. It's a fantastic discussion. I think you're going to get a lot out of it. I did. So stay tuned.
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Ryan Holiday, welcome to the show. Thanks for having me. All right. So your book is The Obstacle
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is the Way. Where did that come from? Can you explain that? Yeah. So, I mean, there's a Zen saying
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the obstacle is the path, right? Which I'd heard before. And for me, so the book is rooted and based
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in the Roman philosophy of Stoicism. And there's a quote from Marcus Aurelius where he says, you know,
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the impediment to action advances action. What stands in the way becomes the way. And I'd seen
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in a different translation where they said the obstacle becomes the way. And so it was this moment
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where I realized that like Eastern and Western philosophy were both saying the exact same thing,
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which to me means it's some sort of eternal truth, right? And so I really liked that phrase. It
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really stuck with me. I think I'm actually going to get it tattooed on my arm this weekend.
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But the idea was the things that we think are holding us back or every time we think there's
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some problem, it's actually like an opportunity to do something, something different, but it's an
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opportunity to make things better, right? And so I wanted the whole book is based around that idea.
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And it's filled with examples and stories of people who actually did that. And I just found that like
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that phrase so clearly articulates a timeless idea that I think all the people that you talk
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about in Art of Manliness, all the people that I've, you know, like admired in the course of my
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life and in the books that I've read, that's, that's the one similarity that they seem to have
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in common, that attitude. Yeah. And that's, I mean, the book is, it's about stoicism, but you don't
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kind of focus on like the history of it. And like, you know, there's lots of books out there like
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that, right? You kind of focus on actual concrete examples of people living today or in the recent
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past. And what I find fascinating, you kind of have, you devote a section to this. It's like all
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these great men and great people from history, like they were drawn to stoicism. Like they had,
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they read the stoics all the time. What is it about stoicism that draws these sort of
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Well, I think what's, I think it goes down to, and yeah, to go to your point, like, I don't think
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anyone wakes up in the morning and thinks like, oh, I need more philosophy in my life because
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philosophy seems like an abstract theoretical college course that doesn't actually help you
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with your problems. And I think what sets stoicism apart from that, and this goes to your question is
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it was actually by, it was actually written by people who do things or who did things like
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Aristotle is very smart, but like he was an academic, right? That's what he did. He was,
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he was a smart guy who wrote about the world, but it was inherently limited by the fact that
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he just wrote about the world rather than living in it, right? He was Alexander's academic advisor and
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teacher, but he wasn't out like leading the troops with Alexander, right? But the difference between
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Aristotle and Marcus Aurelius and Seneca and Epictetus is that these were men who lived very trying,
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difficult lives on the sort of, on the, on the battlefield, both literate, both literally and
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figuratively. And so the philosophy is rooted in action. You know, Marcus Aurelius is the most
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powerful man in the world. Seneca is a, is an influential businessman and an advisor to powerful
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politicians. Epictetus, although a teacher, was a freed slave. So he, he, these weren't theoretical
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explanations about how the world works. This was, this was rooted in the school, like sort of
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practicality. And so I think the reason that the philosophy has spread so long is that it's,
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it's written by doers for doers. And then, yeah, I run through some of the people who, who like the
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Stoics. You have Ambrose Bierce, who's a civil war veteran and a contemporary of Mark Twain. You know,
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you have James Stockdale who spent, you know, was a fighter pilot who spent seven and a half years in
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Vietnam prison camps. Frederick the Great, you have Theodore Roosevelt, you have George Washington,
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Thomas Jefferson and a copy of the letters of Epictetus, or the essays of Epictetus on his
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bedside table when he died. You know, Stoicism was written at a very tumultuous time in history.
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And then when you look at other tumultuous times in history, you tend to see it pop back up and find a
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new audience because of who it's meant for and what it talks about.
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Yeah. That's a great point. I just finished reading a book called Roman honor, um, written by,
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I forgot the name of the professor anyways. Uh, she kind of talks about the history of Roman honor,
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right? This idea, like honor is like, this is your reputation, right? And it's like,
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you care about what other people think about you. Um, and she makes the argument that Stoicism
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came to rise in the Roman Republic as the Republic was declining. And so people had like,
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you know, Marcus Aurelius, like they stopped kind of caring what other people thought about them and
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just were more concerned about survival. Right. And it's interesting that we kind of,
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you're right. Like today we see Stoicism on the rise. It seems like a lot of entrepreneurs are
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really into it. I don't know. What is it about today's climate that makes Stoicism so appealing
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again? Sure. Well, I think at its core, Stoicism is rooted on the idea that you don't control the
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world around you. You only control yourself. Right. And it doesn't matter what other people
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are doing. It doesn't matter what they can do to you. It just matters how you respond to that.
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And so I think one, that's, you know, that's the attitude you need in the decline and fall of the
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Roman empire. That's the attitude you needed during the American revolution. You needed during the civil
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war. You needed during the Victorian era. It's, you needed it during the industrial revolution.
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You needed it in a prison camp. And then today you need it in, you know, a time of economic upheaval
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and shifts. And you need it in a world where, you know, what are entrepreneurs, but people who are
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solely responsible for themselves and for other people. Right. Like when you're an employee,
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the idea of Stoicism is perhaps less attractive because the ideas of discipline and self-control
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and they're not as important, right? Because someone's taking care of you, quote unquote.
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And, you know, if you're, if you're starting a company from nothing, it's a high stress. It's a,
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it's a temptation driven, a distraction driven environment where if you're not on your game and
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you're not holding yourself to some sort of standard and you don't have a framework for dealing
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with the problems that you're going to face, you're not going to last very long as an entrepreneur.
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All right. So in the obstacle is the way you kind of distill Stoicism down to like three
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principles. Sure. What are they? And I guess there's a whole bunch of follow-up questions
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we can ask that, but so yeah, let's start off. What are the three kind of distilled principles
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of the obstacles the way? Yeah. So look, I think Stoicism is a bunch of different principles or
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disciplines, right? And I'm focusing on this, this one idea of using Stoicism to turn obstacles
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upside down. Like the Stoics think there is nothing bad that can happen to you because everything
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is an opportunity to practice some virtue and they have a pretty expansive definition
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of virtue, but in every opportunity, even if, if I was trying to do one thing and then
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that's impossible, I can still do all these other things. And so the three disciplines that
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I think are really important to that idea, the first step is perception. That's, that's,
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you know, being able to control your emotions. That's being able to look at things objectively.
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That's being able to sort of shift your perspective. So you can see things from various angles.
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That's, that's having a sort of a strong nerve. So you're not, you know, freaked out by something
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that's hard or difficult. That's having a kind of ambition or a goal. So you're able to see past
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what other people say, you know, is or isn't realistic. So those perceptions are really important.
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And I think the clearest iteration or explanation of that idea is a quote from Epictetus where he says,
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there is no good or bad. There's only perception, right? Things are what they are. We decide whether
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they're good or bad. And if we don't decide they're bad, then they're good. And if we don't
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decide they're, they're good, they're bad. And so if you can look at these things and, and prevent
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yourself from adding these labels and explanations to you, your obstacle is going to be much easier,
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right? The next one is action. And, and I perhaps took more liberty with the action phase than I did
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anywhere else. But, you know, the Stoics were sort of ruled by what they felt like sort of virtue.
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And so that's, you know, thinking of people other than yourselves, that's, that's, you know,
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being just and honorable, as you said. So I'm thinking about how you use those approaches
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to solve problems. I think energy is probably the biggest, you know, people face these problems,
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and they sit around and look for these like perfect solutions to them, right? It's like,
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oh, I need this, I need that. Or like, I tell the story in the book of Amelia Earhart.
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And I may have gotten this example from you, but like, her first offer to fly across the Atlantic,
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was a preposterous offer, right? It's like, we want to have the first female fly across the Atlantic,
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but we're going to send two male chaperones with you. They're going to get paid, you're not,
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you're gonna be crammed in the back of the plane, you're probably going to die. And they're going to
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get most of the attention after. And like, to me, that's very analogous to, I'm sure a lot of people
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that you know, who graduated from college recently, and then they moved back in with their parents,
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because they didn't get the perfect job offer that they felt that they were entitled to, right?
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That's not what a stoic does. A stoic takes what they're given as a given, and works on it from
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there. So for I think the action section is very much about, you know, creativity, it's about
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pragmatism, it's about persistence. There's, there's some military strategy in there where I
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talk about, you know, attacking from the flanks rather than head on, not, not, not having strength
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go against strength. And then the final one is the discipline of the will. And I use Abraham Lincoln
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as the example of this guy who was just sort of a plodding, enduring, patient man, who was able to
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outlast this terrible thing that was the civil war, because he'd suffered from depression his whole
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life. And he sort of, he knew his favorite saying was this idea of this too shall pass. And so that
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last section is about the understanding that there are some things that you can't change in life,
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and you've got to accept them. And you've got to outlast them or, or find the benefit within them.
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Now you've sort of talked about it so far, but this idea that sort of underlies these three
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principles is like inversion, right? Always flipping things. And I think we can see that in the perception
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thing. You want to like look at an obstacle and you want to flip it and say, there's an opportunity
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there. But it, it also seems like it underlies these other two principles, like in action and in
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will. Can, am I, am I right in that or? Yeah, totally. I mean, look, I think a clear example
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of this is if you look back on your own life or if anyone looks back on their own life, they see
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failures that were really awful at the time, but with distance, they almost wouldn't trade those
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failures for anything because we learned from them. We got stronger from them. We look at the bad things
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that happened to us and we realize how often they were blessings in disguise. Right. And so, and yet,
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so we know failure has benefits for us and yet we do everything we can to avoid ever failing. Right.
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We fail sort of kicking and screaming. And so like one of the things I'm talking about is this more
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iterative approach. Instead of trying to perfect everything in the lab, which is what you think you
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need to do to be perfect and prevent bad things from ever happening. In fact, you want to be more
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fluid and iterative. So you're failing on purpose and you're learning from them. So it's like, how can
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you take the worst things in life, whether it's failure and find an advantage of it? I have a
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chapter in there on, on sort of meditating on your own mortality. You know, death is obviously the worst
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thing that can happen to us, but without death, life is meaningless. It just goes on and on and there's
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no sense of urgency. There's no sense of purpose. There's no, um, that means if life is, if life goes
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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
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you could, you can find a motivating, a beneficial factor from it, it's pretty clear to me that you can
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find good things in, in pretty much every aspect of what you're doing.
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Yeah. I mean, one thing that really struck to me was in your section about action talking about,
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you know, attacking from the flank, right? Usually the people want to like, you're going to attack,
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you got to like, just, you got to, you got to move, you got to be the aggressor, right? That's
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what action means. But you make an argument and devote a section to like, no, sometimes that's not
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what you want to do. In fact, you want to just be passive and let them come to you. So you're like
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inverting the action. Yeah. So like, uh, one of my favorite writers is BH Liddell Hart. He was a
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brilliant world war one commander who became a military strategist. He wrote a bunch of excellent
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books, but he did this study of basically, I think he looked at like 250 campaigns throughout
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history. And he was like, what was the decisive battle in all of them? Right. And in almost
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everyone, it was not a head to head confrontation between two major armies. It's not a Napoleonic
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clash between two major, you know, entrenched forces. It was always something around the side
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or a deception or a quick maneuver that caught someone off guard. Right. Like the most decisive
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battle of the revolutionary war was, was, you know, George Washington crossing the Delaware on Christmas
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day to attack troops that might've been drunk. Right. And, and yet when we, like, if you're starting a
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if, if, if someone else wanted to start a site about manliness, that's probably not a good idea.
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If you want the male demographic, don't start another site where you have an entrenched competitor
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who owns a niche, right? You want to find, you want to find the areas where the strong are weak
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and you are strong. And that's where you did it. That's where, that's where you attack. Like force
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doesn't go against force. And when you look at some of the most powerful, effective movements in
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history, whether it's the civil rights movement, whether it's Gandhi or militarily, it's the
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Russians versus Napoleon. And then against the Germans, they just retreated into the interior and
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they let this main army sort of dissipate all its energy until they realized that they'd walked into
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a trap. Right. And so that idea of passive resistance or, or almost a jujitsu move, I think is,
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is highly underrated and it's underrated and underutilized because it's not as
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exciting and it doesn't feel as manly, but if it works, it works. Right.
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Exactly. It's, it's pragmatic. And like the Stokes just all about, yeah, if it works,
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that's what we're going to do. Totally. All right. Um, so yeah, one thing I love about this book
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is you just, there's so many, you, you go to history and you find examples, like concrete
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examples of where these principles applied. I mean, that's, I love that. And that's what we do on the
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art of manliness. We try to do, um, was there a particular instance or example that really
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called out to you personally? Yeah. So what I, and that's what I try to do is I don't want to just
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tell people that this stuff is good. I want to like show examples. And I learned this from Robert
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Green who wrote the 40 laws of power. He's my mentor. And he, he sort of showed me that the
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best way to tell, to make a point is to tell it in a story. So that's, that's what I wanted to do.
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You can just read the original books. If you want the theory, if you want examples, like that's why I
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wrote this book. Um, two favorites. I think my, one of my favorites I actually got from you for
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people who don't know, I, I called Brett, uh, when I was thinking about writing this book and I was
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like, you know, who were your favorite people in history that overcame obstacles that I should look
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at? And ironically, he gave me a female example. He gave me Laura Ingalls Wilder, who, you know,
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you think of as this, you know, like she wrote these books about the prairie, but she lived the life
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that she's talking about in the book. And if you look at it on paper, that life was terrible,
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right? Like who wants to live in like the backwoods of Florida, then like the, the, the prairies of
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Kansas in a, like a, you know, a grass hut, like that would be awful. Right. But she loved it. Like
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she saw it as this adventure. And I have a quote from her in the book where she says, there's good in
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everything. If you look for it, which is, which is actually, you know, a very stoic idea. Shakespeare has
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a similar line where he says, um, nothing good or bad, but thinking makes it so. And so this idea
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of this, this little woman, uh, like, which I guess is funny, but this little woman, this little
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woman just seeing all this, all this adversity as an adventure and that switch turning it from awful
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to amazing. Um, and that's why it's enthralled all these, you know, kids and readers for a hundred
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years now, I think is really great. And I love that story. Two of my favorites, you know, I tell the
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story of Demosthenes who is the, the Athenian order, um, who a lot of people didn't know before
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he became this powerful, you know, speaker who could mobilize the Athenian army against, uh,
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Philip of Macedon was, was a crippled boy with a stutter whose guard, whose parents died. And then
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his guardians stole everything from him. And he, it's almost like a movie montage. Like he,
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he, he overcame his stutter by like filling his mouth with rocks and then talking through them
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or shouting through the wind until he developed these strong lungs. And then at one point built
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an underground study and shaved his head, half of his head. So he'd be too embarrassed to go outside.
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And so it's like, you know, this terrible thing happened to him. He was, you know, he was,
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his trust was violated as a child. He was born disabled. And yet it was precisely those events
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that made him who he ultimately was. And it was in the course of writing those wrongs
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that he developed his reputation as a speaker and eventually became a politician and this
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great influential figure. So I really liked that. This is S Grant, who I think is criminally
00:22:28.840
under, underrated in history as a, as a thinker and a strategist and a man, he wasn't a great
00:22:33.620
president, but whatever. Uh, John D. Rockefeller is one of my favorites. Uh, Amelia Earhart was great.
00:22:39.440
Um, and then Erwin Rommel, I think was a, was a, is obviously a controversial figure,
00:22:44.760
but was really interesting and fascinating as a, as a strategist.
00:22:48.680
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Yeah. Those are all great examples. Just so much you can learn from those people.
00:24:14.440
Well, you know, of course I love Teddy Roosevelt.
00:24:17.000
And I love the Demonstrates one. That was, I mean, his story is just fascinating. And then
00:24:21.880
what was the other one that I like? Well, you know, the hurricane, right? That was a great one.
00:24:26.360
I mean, I think that's a perfect example of living like the obstacle is the way.
00:24:30.760
Like, you just decide I'm not going to be a prisoner. I might be in prison, but I'm not.
00:24:35.240
I'm not. You're not going to treat me as a prisoner.
00:24:37.360
Totally. I just read this amazing article. I forget about which boxer, but I guess there
00:24:41.440
was another boxer at the same time who actually boxed in prison and almost won the heavyweight
00:24:48.700
It was, it's crazy. I think it was on Bleacher Report. It was this crazy long read about
00:24:53.040
this guy who he, like, he would fight in the prison. They would bring boxers and set, like,
00:24:59.140
you know how you're allowed to have jobs in prison, right?
00:25:01.680
Let him, his job be a boxing coach. And, and he, he, he almost won the middleweight, like
00:25:09.180
a belt as a professional boxer in prison. And so to me, like these stories, it's like,
00:25:14.320
look, chances are you and I will not be wrongfully accused of quadruple homicide, like any type
00:25:21.000
scene, right? If all goes to this plan, that won't happen. But at the same time, it surely
00:25:25.480
wasn't Hurricane Carter's plan either. Right. But like, if they can wait out, you know, a
00:25:30.500
20 year prison sentence and somehow come out, not just not worse off, but better off. I'm
00:25:37.560
pretty sure like, you know, the, your deadline getting moved up or you getting laid off from
00:25:44.220
a job or, you know, the economy tanking. These are not nearly as catastrophic of events as
00:25:51.280
we're telling ourselves right now, because that's how they feel.
00:25:55.400
Yeah. Well, here's a question I have. As I was reading this, you read these examples from
00:25:59.620
history and like the obstacles that these people face were like, they were like tough stuff,
00:26:03.260
like war, famine, death, harsh weather, whatever poverty. And like, it's sort of sort of counterintuitive.
00:26:10.360
Like I've encountered like physically hard things in my life and tragedies in my life, but for some
00:26:15.980
weird reason, like it was hard, but like, it seemed easier to overcome than like some of those more
00:26:21.860
intangible and internal problems in your head. Do you agree with that? And if so, why do you think
00:26:28.160
that is like, why is it easier to like confront like a, you know, a physical challenge or a tragedy
00:26:33.860
than it is sort of like the daily grind of life? Sure. Well, I wonder if part of it is like
00:26:38.800
biologically we're like designed to, it's more imperative that we survive those than the other
00:26:45.040
problems, right? Like your genes don't care if you're as happy as much as they care that you just
00:26:50.900
don't die. You know what I mean? Yeah. Yeah. That's, that's part of it. And then I think I,
00:26:55.940
one of the things that I realized in the book is that you look at these terrible things that these
00:27:00.180
people went through and like, it wasn't, sometimes it wasn't even like the worst thing that they ever
00:27:05.460
went through. Right. Like, and, and you realize it's because they had this kind of frame, one,
00:27:10.940
they had a framework for dealing with obstacles. And I think stoicism was a big part of that,
00:27:14.220
but two, when, when the world felt much more unpredictable and capricious than it does now,
00:27:20.760
it was easier to take these things in stride, you know? Um, and, and like when a tornado could
00:27:29.480
come and you didn't know what a tornado was and you just thought the hand of God was turning your
00:27:34.720
town upside down, right? You'd be a little less conceited and pretentious and delusional about how
00:27:41.560
safe you were at any given moment. When like your wife unexpectedly dies, um, and you didn't know it was
00:27:49.120
because the cut on her finger got it like infected. You, you would be more humble about, you know,
00:27:55.040
tempting fate and taking things for granted, I would say. And I, but I also wonder if just being
00:28:00.420
consumed by that fear and doubt made some of the emotional problems take a back seat. And so now
00:28:07.700
having dealt with some of that stuff, we, we feel more insulated and yet we don't have that framework
00:28:14.240
that they did to deal with tough problems. And I think we need that. And I also, the final thing
00:28:19.420
though, I would say is like, I don't want to discount anyone's emotional or difficult problems.
00:28:24.160
Like, you know, your girlfriend dumps you. It can literally feel like the world is ending and,
00:28:29.600
and it feels really awful and that's tough. And I don't want people to say like, to pretend that
00:28:37.960
they don't feel pain and that it's not bad because they like, it's certainly better than being like
00:28:43.500
stomped on by an elephant. Yeah. Well, that's a good point about how we, you know, we live in a
00:28:48.720
time of relative, like it's the safest time in human history. Right. But yet we still think it's
00:28:54.040
the most dangerous time. Like, Oh, it's so horrible out there. And I guess it's because there's so few
00:28:59.400
instances of like crime or violence or mayhem that when it does happen, it's just like, Holy cow,
00:29:05.300
this is the worst, worst ever. When that stuff happened all the time. Sure. I mean, look,
00:29:10.320
you and I are talking to each other on high definition video states apart from each other
00:29:15.560
for free. Yeah. Right. Like this, it's crazy and you're recording it and it's going to go on a
00:29:19.880
website and be seen by millions of people. Like it's very easy when you, when those things are
00:29:24.980
commonplace in your life to start to assume that like the world has been tamed or domesticated and that
00:29:31.340
all the sharp edges have been rounded off. And ironically, and this is what the Stoics talk
00:29:36.340
about, that makes the bad things feel so much worse because you're never anticipating them.
00:29:42.540
So I talk a lot about that. It's like, you would be much better off if you thought about the worst
00:29:47.100
case scenario more often. Yeah. And I'm not saying that you should be a pessimist, but if you're not
00:29:51.860
anticipating and you're not, there was a, uh, meditatio malorum, the idea of premeditation of
00:29:58.000
evils, like what could go wrong? This is what I'm planning, but I understand that X, Y, or Z could
00:30:04.980
happen. And that this is what I plan to do about them prepares you and doles the surprise or the
00:30:13.620
shock in a much beneficial way. Yeah. I think it's interesting too that, okay. So like, you know,
00:30:18.400
the Romans, the Stoics, like, yeah, they faced, like it was a horrible time then, but like what I
00:30:24.000
found is like the people who were drawn to it were like successful people, people who could
00:30:29.040
were relatively probably sheltered from a lot of that stuff. And like, it seems like they were
00:30:33.320
drawn to it as a way to, I don't know, harden themselves up. No, I think that's a great insight.
00:30:38.460
And what a lot of people miss is they think that Stoicism, because they read these exercises and they
00:30:42.800
hear, it's like, Oh, you should think about the worst thing that should happen. And you should prepare
00:30:46.740
for poverty and warfare. And they think that it's depressing. Right. And that these must've been just
00:30:52.640
really downer people. And in fact, no, it's sort of like, um, it's almost like a bias by omission
00:30:58.980
that, that has been wrongly deduced, um, by a lot of the readers. Nobody needs help. Like what the
00:31:05.380
Stoics believed was nobody needs help, like being reminded, like what happiness feels like and why
00:31:11.260
you should smile and love your children and like, like having sex. And like, you don't need a book that
00:31:18.000
like tells you these things are good, right? That's natural. Like feeling good when you're
00:31:22.740
successful, that's sort of biologically takes care of itself. But the Stoics felt is like,
00:31:29.060
what we need is that we need that counterbalance. We need the reminders. So we don't get too exuberant
00:31:35.140
in either direction or too extreme. And these were reminders to sort of center themselves. They weren't,
00:31:42.060
it wasn't like depressing people telling themselves depressing things. It was normal people
00:31:48.060
girding themselves and preparing themselves for things that they hoped wouldn't happen,
00:31:55.420
but they knew very well could happen. Yeah. Yeah. It's, it's, it's really fascinating.
00:32:01.560
So when I was reading the book, the ones, I mean, all of it's really great, but the one section that hit
00:32:05.060
home to me for some reason was in your section about the will and about perseverance.
00:32:10.780
And I feel like all of us have this tendency to believe that everything, if, you know,
00:32:17.200
we're waiting for things just to be just right. Like we're waiting for Plato's Republic. Right.
00:32:21.720
And, and instead, you know, how do you overcome that? Because I know it's not true, right? I keep
00:32:26.980
on thinking, okay, if everything was just this way, then my life will be awesome. But never, I mean,
00:32:31.320
you have kids, man, like nothing goes as planned. So how do we overcome this tendency to believe that
00:32:37.420
my life will be great if things were just so? Sure. Well, I, I sort of, I make the distinction
00:32:43.480
in the book and the, in the action, I talk about persistence, which is just sort of staying at it
00:32:47.820
and hammering away. And then persistence or sorry, perseverance, I say is sort of something deeper
00:32:54.140
and larger. That's like that deep endurance. Like, you know, you have to be persistent to train
00:32:58.880
yourself to run like five miles. But if you want to do like an ultra marathon, like you have to have
00:33:03.940
this deep iron part of you that you can rely on when, when things are awful and you, you just want
00:33:10.900
to quit. And so like, I'm not, I'm not sure if there's like a recipe other than like, you just
00:33:18.460
have to develop this skill over time, you know? And, and you have to, you have to realize that like
00:33:23.860
things can not go the way that you wanted and things can be bad and people can prevent you from
00:33:29.900
doing what you want, but they can never prevent you from holding on, right? Like you can get
00:33:34.800
rejected by every, you know, record label in the world, but it's ultimately up to you when you decide
00:33:40.680
to quit music, you know? Like I can put out this book and it can sell zero copies, but it's ultimately
00:33:46.500
up to me. I make the final decision on whether this is like a failure that I quit. Like no one can ever
00:33:53.380
take the ability to persevere away from you other than death. Right. And, and that's what I think
00:34:00.620
that's what these people had. Like I quote, um, there's this line about Magellan and someone was
00:34:07.220
like, you know, what was his greatest skill? And his greatest skill was that he could endure hunger
00:34:11.820
better than the other men. Like he just had a little bit extra in the tank and he wanted it worse
00:34:17.540
than them or wanted it more than them. And he just wouldn't give up and he would endure whatever it took
00:34:22.160
to get there. And I think that's really important. And I also think that's the opposite of what a lot
00:34:27.820
of us are taught. And a lot of us don't develop that skill. You know, like we talked about Theodore
00:34:35.000
Roosevelt, like he's born with asthma. I remember kids my age having asthma and it's like, they can't
00:34:40.520
play sports. They can't do that. Their life was defined by what they can't. Yeah. Rather than like,
00:34:47.340
rather than being someone like Theodore Roosevelt, who's like, who almost took that as a challenge.
00:34:51.840
And I think the book is about seeing those things as a challenge rather than a constraint.
00:34:57.500
Yeah. Well, are there any examples from your own life where you turned an obstacle into an
00:35:02.440
opportunity? Yeah. So that's the one question that I probably got the most when I've been doing stuff
00:35:07.960
for this book and in a weird way. And I know it probably sounds like I'm dancing around it. I kind
00:35:11.760
of, I kind of like say like that question because, because like, this isn't about me, right?
00:35:17.500
Like this is about like a framework for overcoming obstacles that yes, I've personally used and took
00:35:22.980
a lot out of, but I also like, I wrote the book for myself, right? Like I wrote the book so I could
00:35:28.300
get better at it. I'm not in the book at all. I'm not talking about myself in the book, but I'm
00:35:33.900
talking about like, this is what's worked and we can all use it. But like, you know, we all go through
00:35:40.040
stuff in our lives. Like, you know, I dropped out of college at 19, you know, my, my life has been
00:35:45.060
high stakes, high pressure for as long as I can remember. And every day there's been problems
00:35:52.600
and things that made me want to quit or make me want to stop. And I have to remind myself that
00:35:58.560
these are, these are challenges that are making me better. These are opportunities to do stuff.
00:36:05.080
Like I'm in the middle of something now with some of my business partners and it's like, it's awful.
00:36:09.140
And then I, it's like, but it's also forcing me to have confrontations or conversations that I would
00:36:14.620
rather not have that I'm getting better from. And I'm learning from, and I'm figuring out,
00:36:19.780
I'm figuring out what I don't want, like from this exact experience. And I think it's that attitude
00:36:26.400
that's helped me, you know, achieve what I've achieved, but I would much prefer to put the
00:36:31.520
spotlight on other more relatable challenges because I don't want, I don't want to talk to someone
00:36:37.960
who's had to over, who was born into, you know, abject poverty and say like, look, I know what
00:36:43.560
you were going through because like, you know, my first world problems were really tough for me to
00:36:50.140
go through. Well, it's interesting that you said, you know, you wrote this book for yourself. It sounds
00:36:54.560
like very much like Marcus Aurelius, you know, his meditations, like we read them, but like, that was
00:36:59.200
like for him only really. Totally. Yeah. Like, like the most of the stoic works, like they weren't
00:37:05.400
works for publication. They were like stoicism is a series of exercises and turning the obstacle
00:37:11.000
upside down is an exercise. And they would write examples or anecdotes or new phrasing to help them
00:37:19.380
like be better at it. And for me, I was trying to write the book, like, yeah, I'm a writer. So I
00:37:25.280
write things. So it's a little bit different, but like I was trying, I was thinking about myself when
00:37:30.400
I was writing this stuff and thinking about the times that I did the opposite of this stuff and
00:37:35.320
what I wish I'd done instead and what I want to do next time. Yeah. That's awesome. Is there
00:37:40.280
something like, I always like to end the podcast with like, you know, sort of like a takeaway,
00:37:43.700
like what can I do now or an action point? Like, is there one thing that you think a person who's
00:37:48.040
listening to this podcast right now can do today that they'll experience like a payoff, right? You know,
00:37:53.000
they'll be like, man, that's, that's, this is helping me, um, that from the obstacles of the
00:37:57.560
way. Sure. I guess, I guess I would, I think this mental flip is really easy to apply. It's not easy
00:38:04.600
to do and live by. It's easy to think about. It's like, take the worst thing that ever happened to you
00:38:11.520
and then think about the benefits that you derived from that, you know, like getting rejected from this,
00:38:18.360
getting kicked out of that, you know, quitting this, and then think about what happened after.
00:38:25.940
And I think you'll see the, I think you'll see that it wasn't all bad, that there were real benefits.
00:38:30.180
And then instead of waiting five years or 10 years or 20 years afterwards to get those benefits,
00:38:38.420
why don't you start thinking about them now? So whatever that thing that you're afraid of,
00:38:42.260
um, or this thing that's in front of you or facing you, you know, like what can you,
00:38:47.600
what benefits are inherent within it? And can you focus and lean into those? And does that make,
00:38:54.280
you know, the, the, the pill, so to speak, easier to swallow?
00:38:58.380
Yeah, that's great stuff. And I think that will really help out a lot. And what I love too, about
00:39:02.200
your, the book and your, just the, what you're putting out here is that it's, yeah, it's easy to
00:39:08.100
think about, but it's hard to put in practice, but I love that. It's like a challenge that it's
00:39:12.000
like, it's not going to happen right away. It's sort of a lifelong process.
00:39:16.180
Sure. And look, I also think like, look, I wrote this book to convey like wisdom that a lot of
00:39:21.640
people smarter than me and put down on paper or in history over the years. But like, I also just
00:39:27.300
want to remind people, it's like, look, whatever you're going through, chances are a hundred years
00:39:31.340
ago, someone went through more or less the same thing, but probably worse. Right. Um, like, you know,
00:39:36.900
your, your money is tight, like, but you know, at least debtors prisons don't exist. Right. Or
00:39:43.560
whatever. Right. Like things were much worse before. And this, this is a great time. But so
00:39:48.140
those people, many of them wrote about what they went through and gave very explicit advice and
00:39:55.060
lessons. Um, you know, there's, there's a, um, there's a great line from Bismarck, I think,
00:40:00.620
where he's saying like, you know, any fool can learn from experience. I prefer to learn from
00:40:05.740
other people's experiences. Like there's a bibliography in this book. You know, I have
00:40:11.000
my reading list where I give out recommendations. Like there's so many books out there of people
00:40:15.520
giving amazing advice on dealing with tough, crappy problems, like benefit from that knowledge.
00:40:22.400
Don't do it by yourself and white knuckle it when you don't have to.
00:40:25.880
Yeah. That's awesome. Well, Ryan, where can people find out about The Obstacle is the Way?
00:40:30.520
Yeah. So, uh, theobstaclestheway.natter.com I think is the website. My website's Ryan
00:40:35.680
Holliday.net. The book is available in bookstores everywhere. Uh, it's on Amazon. Check it out. Uh,
00:40:42.560
I hope you really like it. And I always take emails from people who have questions. It's just
00:40:46.280
my name and, uh, at Gmail. Awesome. Well, Ryan Holliday, thank you very much. It's been a pleasure.
00:40:50.860
Thanks for having me, man. Our guest today was Ryan Holliday. Ryan is the author of the book,
00:40:54.800
The Obstacle is the Way, The Timeless Art of Turning Adversity into Advantage. The book is releasing
00:41:00.960
on May 1st. You can find that on amazon.com. You can also find out information about his book at
00:41:07.160
theobstacleistheway.com. I highly recommend you go pick up a copy. It's a quick read, but it's just
00:41:12.700
packed with information. I've read it twice already. I'll probably be reading again pretty soon
00:41:16.720
because it's so, it's just got so much great, useful, and inspirational information. So go check
00:41:22.220
it out. Well, that wraps up another edition of the Art of Manliness podcast. For more manly tips and
00:41:28.960
advice, make sure to check out the Art of Manliness website at artofmanliness.com.