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

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00:01:27.780 Brett McKay here and welcome to another edition of the Art of Manliness podcast. Well, a common

00:01:43.020 thing that we have on the podcast and on the website is this idea of overcoming adversity.

00:01:47.640 Our goal is to help men become resilient in the face of adversity and, you know, whatever challenges

00:01:52.780 you might have, whether it's economic or physical or emotional or mental, we want to help you overcome

00:01:59.440 that so you can achieve the goals that you have for yourself. And this whole idea of overcoming

00:02:05.000 adversity or being resilient in the face of adversity has been a concern for philosophers and great men

00:02:10.820 through history for eons. And a group of men that really took this matter to heart were the Stoic

00:02:16.340 philosophers of ancient Greece and Rome, where they developed the whole philosophy and ethic on how to

00:02:21.940 remain calm and in control, even when things are just going to pot around you. The Stoic philosophy

00:02:29.620 has been popular amongst just great men from history, founding fathers. Many of them were

00:02:35.980 students of Stoic philosophy. Generals have been students of Stoic philosophy. Anyways, I'm a big fan

00:02:42.000 of Stoicism. Our guest today has been a student of Stoicism. He's written about it and he's taken

00:02:49.720 Stoicism, used it as a lens to look at the lives of great men and women to see how they applied Stoic

00:02:56.800 principles to turn adversity into opportunities. His name is Ryan Holiday, and his book is The Obstacle

00:03:03.360 is the Way, The Timeless Art of Turning Trials into Triumph. Today, Ryan and I are going to talk about

00:03:09.000 Stoicism. We're going to talk about the three principles that he lays out on turning obstacles

00:03:13.880 into opportunities. We're also going to discuss great men and women from history who overcame

00:03:21.260 insurmountable odds to do great things and actually use that challenge as a catapult to do amazing

00:03:28.540 things. And we're going to talk about how you can apply this into your own life. It's a fantastic

00:03:33.460 podcast. It's a fantastic discussion. I think you're going to get a lot out of it. I did. So stay tuned.

00:03:38.640 Ryan Holiday, welcome to the show. Thanks for having me. All right. So your book is The Obstacle

00:03:48.500 is the Way. Where did that come from? Can you explain that? Yeah. So, I mean, there's a Zen saying

00:03:54.940 the obstacle is the path, right? Which I'd heard before. And for me, so the book is rooted and based

00:04:02.980 in the Roman philosophy of Stoicism. And there's a quote from Marcus Aurelius where he says, you know,

00:04:09.480 the impediment to action advances action. What stands in the way becomes the way. And I'd seen

00:04:14.800 in a different translation where they said the obstacle becomes the way. And so it was this moment

00:04:19.940 where I realized that like Eastern and Western philosophy were both saying the exact same thing,

00:04:25.220 which to me means it's some sort of eternal truth, right? And so I really liked that phrase. It

00:04:29.660 really stuck with me. I think I'm actually going to get it tattooed on my arm this weekend.

00:04:33.440 But the idea was the things that we think are holding us back or every time we think there's

00:04:38.340 some problem, it's actually like an opportunity to do something, something different, but it's an

00:04:43.740 opportunity to make things better, right? And so I wanted the whole book is based around that idea.

00:04:49.420 And it's filled with examples and stories of people who actually did that. And I just found that like

00:04:55.380 that phrase so clearly articulates a timeless idea that I think all the people that you talk

00:05:02.400 about in Art of Manliness, all the people that I've, you know, like admired in the course of my

00:05:07.600 life and in the books that I've read, that's, that's the one similarity that they seem to have

00:05:12.660 in common, that attitude. Yeah. And that's, I mean, the book is, it's about stoicism, but you don't

00:05:17.280 kind of focus on like the history of it. And like, you know, there's lots of books out there like

00:05:22.100 that, right? You kind of focus on actual concrete examples of people living today or in the recent

00:05:27.620 past. And what I find fascinating, you kind of have, you devote a section to this. It's like all

00:05:31.800 these great men and great people from history, like they were drawn to stoicism. Like they had,

00:05:36.940 they read the stoics all the time. What is it about stoicism that draws these sort of

00:05:41.340 great souls to the philosophy?

00:05:44.280 Well, I think what's, I think it goes down to, and yeah, to go to your point, like, I don't think

00:05:49.040 anyone wakes up in the morning and thinks like, oh, I need more philosophy in my life because

00:05:53.120 philosophy seems like an abstract theoretical college course that doesn't actually help you

00:05:59.940 with your problems. And I think what sets stoicism apart from that, and this goes to your question is

00:06:04.940 it was actually by, it was actually written by people who do things or who did things like

00:06:09.960 Aristotle is very smart, but like he was an academic, right? That's what he did. He was,

00:06:15.780 he was a smart guy who wrote about the world, but it was inherently limited by the fact that

00:06:21.160 he just wrote about the world rather than living in it, right? He was Alexander's academic advisor and

00:06:27.620 teacher, but he wasn't out like leading the troops with Alexander, right? But the difference between

00:06:33.460 Aristotle and Marcus Aurelius and Seneca and Epictetus is that these were men who lived very trying,

00:06:40.500 difficult lives on the sort of, on the, on the battlefield, both literate, both literally and

00:06:47.120 figuratively. And so the philosophy is rooted in action. You know, Marcus Aurelius is the most

00:06:52.460 powerful man in the world. Seneca is a, is an influential businessman and an advisor to powerful

00:06:58.080 politicians. Epictetus, although a teacher, was a freed slave. So he, he, these weren't theoretical

00:07:08.220 explanations about how the world works. This was, this was rooted in the school, like sort of

00:07:13.660 practicality. And so I think the reason that the philosophy has spread so long is that it's,

00:07:19.480 it's written by doers for doers. And then, yeah, I run through some of the people who, who like the

00:07:25.780 Stoics. You have Ambrose Bierce, who's a civil war veteran and a contemporary of Mark Twain. You know,

00:07:30.600 you have James Stockdale who spent, you know, was a fighter pilot who spent seven and a half years in

00:07:35.940 Vietnam prison camps. Frederick the Great, you have Theodore Roosevelt, you have George Washington,

00:07:41.340 Thomas Jefferson and a copy of the letters of Epictetus, or the essays of Epictetus on his

00:07:46.940 bedside table when he died. You know, Stoicism was written at a very tumultuous time in history.

00:07:54.460 And then when you look at other tumultuous times in history, you tend to see it pop back up and find a

00:08:01.800 new audience because of who it's meant for and what it talks about.

00:08:05.480 Yeah. That's a great point. I just finished reading a book called Roman honor, um, written by,

00:08:09.840 I forgot the name of the professor anyways. Uh, she kind of talks about the history of Roman honor,

00:08:14.540 right? This idea, like honor is like, this is your reputation, right? And it's like,

00:08:18.700 you care about what other people think about you. Um, and she makes the argument that Stoicism

00:08:23.580 came to rise in the Roman Republic as the Republic was declining. And so people had like,

00:08:30.280 you know, Marcus Aurelius, like they stopped kind of caring what other people thought about them and

00:08:34.080 just were more concerned about survival. Right. And it's interesting that we kind of,

00:08:38.600 you're right. Like today we see Stoicism on the rise. It seems like a lot of entrepreneurs are

00:08:42.720 really into it. I don't know. What is it about today's climate that makes Stoicism so appealing

00:08:49.420 again? Sure. Well, I think at its core, Stoicism is rooted on the idea that you don't control the

00:08:55.780 world around you. You only control yourself. Right. And it doesn't matter what other people

00:09:00.340 are doing. It doesn't matter what they can do to you. It just matters how you respond to that.

00:09:05.360 And so I think one, that's, you know, that's the attitude you need in the decline and fall of the

00:09:09.500 Roman empire. That's the attitude you needed during the American revolution. You needed during the civil 1.00

00:09:14.280 war. You needed during the Victorian era. It's, you needed it during the industrial revolution. 0.63

00:09:19.000 You needed it in a prison camp. And then today you need it in, you know, a time of economic upheaval

00:09:26.180 and shifts. And you need it in a world where, you know, what are entrepreneurs, but people who are

00:09:31.680 solely responsible for themselves and for other people. Right. Like when you're an employee,

00:09:37.880 the idea of Stoicism is perhaps less attractive because the ideas of discipline and self-control

00:09:45.080 and they're not as important, right? Because someone's taking care of you, quote unquote.

00:09:51.400 And, you know, if you're, if you're starting a company from nothing, it's a high stress. It's a,

00:09:57.840 it's a temptation driven, a distraction driven environment where if you're not on your game and

00:10:03.780 you're not holding yourself to some sort of standard and you don't have a framework for dealing

00:10:08.000 with the problems that you're going to face, you're not going to last very long as an entrepreneur.

00:10:12.080 All right. So in the obstacle is the way you kind of distill Stoicism down to like three

00:10:16.800 principles. Sure. What are they? And I guess there's a whole bunch of follow-up questions

00:10:21.860 we can ask that, but so yeah, let's start off. What are the three kind of distilled principles

00:10:24.840 of the obstacles the way? Yeah. So look, I think Stoicism is a bunch of different principles or

00:10:29.540 disciplines, right? And I'm focusing on this, this one idea of using Stoicism to turn obstacles

00:10:34.880 upside down. Like the Stoics think there is nothing bad that can happen to you because everything

00:10:40.080 is an opportunity to practice some virtue and they have a pretty expansive definition

00:10:45.300 of virtue, but in every opportunity, even if, if I was trying to do one thing and then

00:10:49.960 that's impossible, I can still do all these other things. And so the three disciplines that

00:10:55.160 I think are really important to that idea, the first step is perception. That's, that's,

00:10:59.800 you know, being able to control your emotions. That's being able to look at things objectively.

00:11:05.380 That's being able to sort of shift your perspective. So you can see things from various angles.

00:11:11.160 That's, that's having a sort of a strong nerve. So you're not, you know, freaked out by something

00:11:15.620 that's hard or difficult. That's having a kind of ambition or a goal. So you're able to see past

00:11:21.240 what other people say, you know, is or isn't realistic. So those perceptions are really important.

00:11:27.480 And I think the clearest iteration or explanation of that idea is a quote from Epictetus where he says,

00:11:33.820 there is no good or bad. There's only perception, right? Things are what they are. We decide whether

00:11:40.460 they're good or bad. And if we don't decide they're bad, then they're good. And if we don't

00:11:44.900 decide they're, they're good, they're bad. And so if you can look at these things and, and prevent

00:11:49.660 yourself from adding these labels and explanations to you, your obstacle is going to be much easier,

00:11:55.700 right? The next one is action. And, and I perhaps took more liberty with the action phase than I did

00:12:01.420 anywhere else. But, you know, the Stoics were sort of ruled by what they felt like sort of virtue.

00:12:06.320 And so that's, you know, thinking of people other than yourselves, that's, that's, you know,

00:12:11.340 being just and honorable, as you said. So I'm thinking about how you use those approaches

00:12:17.040 to solve problems. I think energy is probably the biggest, you know, people face these problems,

00:12:23.660 and they sit around and look for these like perfect solutions to them, right? It's like,

00:12:29.820 oh, I need this, I need that. Or like, I tell the story in the book of Amelia Earhart.

00:12:34.940 And I may have gotten this example from you, but like, her first offer to fly across the Atlantic,

00:12:40.660 was a preposterous offer, right? It's like, we want to have the first female fly across the Atlantic, 0.84

00:12:45.560 but we're going to send two male chaperones with you. They're going to get paid, you're not, 0.99

00:12:50.460 you're gonna be crammed in the back of the plane, you're probably going to die. And they're going to

00:12:55.080 get most of the attention after. And like, to me, that's very analogous to, I'm sure a lot of people

00:13:00.440 that you know, who graduated from college recently, and then they moved back in with their parents,

00:13:05.760 because they didn't get the perfect job offer that they felt that they were entitled to, right?

00:13:10.340 That's not what a stoic does. A stoic takes what they're given as a given, and works on it from

00:13:17.300 there. So for I think the action section is very much about, you know, creativity, it's about

00:13:22.080 pragmatism, it's about persistence. There's, there's some military strategy in there where I

00:13:28.120 talk about, you know, attacking from the flanks rather than head on, not, not, not having strength

00:13:35.440 go against strength. And then the final one is the discipline of the will. And I use Abraham Lincoln

00:13:41.160 as the example of this guy who was just sort of a plodding, enduring, patient man, who was able to

00:13:48.440 outlast this terrible thing that was the civil war, because he'd suffered from depression his whole

00:13:54.160 life. And he sort of, he knew his favorite saying was this idea of this too shall pass. And so that

00:14:00.080 last section is about the understanding that there are some things that you can't change in life,

00:14:05.680 and you've got to accept them. And you've got to outlast them or, or find the benefit within them.

00:14:13.200 We're going to take a short break for a word from our sponsor.

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00:14:45.600 Now you've sort of talked about it so far, but this idea that sort of underlies these three

00:14:49.840 principles is like inversion, right? Always flipping things. And I think we can see that in the perception

00:14:54.500 thing. You want to like look at an obstacle and you want to flip it and say, there's an opportunity

00:14:57.780 there. But it, it also seems like it underlies these other two principles, like in action and in

00:15:03.120 will. Can, am I, am I right in that or? Yeah, totally. I mean, look, I think a clear example

00:15:08.680 of this is if you look back on your own life or if anyone looks back on their own life, they see

00:15:13.860 failures that were really awful at the time, but with distance, they almost wouldn't trade those

00:15:21.240 failures for anything because we learned from them. We got stronger from them. We look at the bad things

00:15:26.240 that happened to us and we realize how often they were blessings in disguise. Right. And so, and yet,

00:15:33.680 so we know failure has benefits for us and yet we do everything we can to avoid ever failing. Right.

00:15:40.760 We fail sort of kicking and screaming. And so like one of the things I'm talking about is this more

00:15:45.580 iterative approach. Instead of trying to perfect everything in the lab, which is what you think you

00:15:50.360 need to do to be perfect and prevent bad things from ever happening. In fact, you want to be more

00:15:55.840 fluid and iterative. So you're failing on purpose and you're learning from them. So it's like, how can

00:16:01.520 you take the worst things in life, whether it's failure and find an advantage of it? I have a

00:16:07.300 chapter in there on, on sort of meditating on your own mortality. You know, death is obviously the worst

00:16:12.620 thing that can happen to us, but without death, life is meaningless. It just goes on and on and there's

00:16:19.340 no sense of urgency. There's no sense of purpose. There's no, um, that means if life is, if life goes

00:16:27.440 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

00:16:33.280 you could, you can find a motivating, a beneficial factor from it, it's pretty clear to me that you can

00:16:39.300 find good things in, in pretty much every aspect of what you're doing.

00:16:44.660 Yeah. I mean, one thing that really struck to me was in your section about action talking about,

00:16:49.540 you know, attacking from the flank, right? Usually the people want to like, you're going to attack,

00:16:53.320 you got to like, just, you got to, you got to move, you got to be the aggressor, right? That's

00:16:57.440 what action means. But you make an argument and devote a section to like, no, sometimes that's not

00:17:01.600 what you want to do. In fact, you want to just be passive and let them come to you. So you're like

00:17:07.360 inverting the action. Yeah. So like, uh, one of my favorite writers is BH Liddell Hart. He was a

00:17:12.860 brilliant world war one commander who became a military strategist. He wrote a bunch of excellent

00:17:16.840 books, but he did this study of basically, I think he looked at like 250 campaigns throughout

00:17:22.220 history. And he was like, what was the decisive battle in all of them? Right. And in almost

00:17:27.960 everyone, it was not a head to head confrontation between two major armies. It's not a Napoleonic

00:17:36.140 clash between two major, you know, entrenched forces. It was always something around the side

00:17:43.380 or a deception or a quick maneuver that caught someone off guard. Right. Like the most decisive

00:17:49.300 battle of the revolutionary war was, was, you know, George Washington crossing the Delaware on Christmas

00:17:55.160 day to attack troops that might've been drunk. Right. And, and yet when we, like, if you're starting a

00:18:01.960 if, if, if someone else wanted to start a site about manliness, that's probably not a good idea.

00:18:08.260 If you want the male demographic, don't start another site where you have an entrenched competitor

00:18:13.740 who owns a niche, right? You want to find, you want to find the areas where the strong are weak

00:18:19.340 and you are strong. And that's where you did it. That's where, that's where you attack. Like force

00:18:23.540 doesn't go against force. And when you look at some of the most powerful, effective movements in

00:18:28.700 history, whether it's the civil rights movement, whether it's Gandhi or militarily, it's the

00:18:34.320 Russians versus Napoleon. And then against the Germans, they just retreated into the interior and 0.58

00:18:38.920 they let this main army sort of dissipate all its energy until they realized that they'd walked into

00:18:45.140 a trap. Right. And so that idea of passive resistance or, or almost a jujitsu move, I think is,

00:18:52.100 is highly underrated and it's underrated and underutilized because it's not as

00:18:58.600 exciting and it doesn't feel as manly, but if it works, it works. Right.

00:19:04.260 Exactly. It's, it's pragmatic. And like the Stokes just all about, yeah, if it works,

00:19:07.960 that's what we're going to do. Totally. All right. Um, so yeah, one thing I love about this book

00:19:12.620 is you just, there's so many, you, you go to history and you find examples, like concrete

00:19:17.100 examples of where these principles applied. I mean, that's, I love that. And that's what we do on the

00:19:20.820 art of manliness. We try to do, um, was there a particular instance or example that really

00:19:26.420 called out to you personally? Yeah. So what I, and that's what I try to do is I don't want to just

00:19:33.000 tell people that this stuff is good. I want to like show examples. And I learned this from Robert

00:19:38.560 Green who wrote the 40 laws of power. He's my mentor. And he, he sort of showed me that the

00:19:42.200 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.

00:19:47.080 You can just read the original books. If you want the theory, if you want examples, like that's why I

00:19:52.240 wrote this book. Um, two favorites. I think my, one of my favorites I actually got from you for

00:19:57.240 people who don't know, I, I called Brett, uh, when I was thinking about writing this book and I was

00:20:01.480 like, you know, who were your favorite people in history that overcame obstacles that I should look

00:20:07.620 at? And ironically, he gave me a female example. He gave me Laura Ingalls Wilder, who, you know,

00:20:14.100 you think of as this, you know, like she wrote these books about the prairie, but she lived the life

00:20:19.300 that she's talking about in the book. And if you look at it on paper, that life was terrible,

00:20:23.500 right? Like who wants to live in like the backwoods of Florida, then like the, the, the prairies of

00:20:29.140 Kansas in a, like a, you know, a grass hut, like that would be awful. Right. But she loved it. Like

00:20:35.000 she saw it as this adventure. And I have a quote from her in the book where she says, there's good in

00:20:40.140 everything. If you look for it, which is, which is actually, you know, a very stoic idea. Shakespeare has

00:20:45.300 a similar line where he says, um, nothing good or bad, but thinking makes it so. And so this idea

00:20:51.040 of this, this little woman, uh, like, which I guess is funny, but this little woman, this little

00:20:57.000 woman just seeing all this, all this adversity as an adventure and that switch turning it from awful

00:21:04.060 to amazing. Um, and that's why it's enthralled all these, you know, kids and readers for a hundred

00:21:09.560 years now, I think is really great. And I love that story. Two of my favorites, you know, I tell the

00:21:14.320 story of Demosthenes who is the, the Athenian order, um, who a lot of people didn't know before

00:21:21.160 he became this powerful, you know, speaker who could mobilize the Athenian army against, uh,

00:21:27.340 Philip of Macedon was, was a crippled boy with a stutter whose guard, whose parents died. And then

00:21:36.440 his guardians stole everything from him. And he, it's almost like a movie montage. Like he,

00:21:42.620 he, he overcame his stutter by like filling his mouth with rocks and then talking through them

00:21:48.120 or shouting through the wind until he developed these strong lungs. And then at one point built

00:21:54.700 an underground study and shaved his head, half of his head. So he'd be too embarrassed to go outside.

00:22:01.140 And so it's like, you know, this terrible thing happened to him. He was, you know, he was,

00:22:05.960 his trust was violated as a child. He was born disabled. And yet it was precisely those events

00:22:12.100 that made him who he ultimately was. And it was in the course of writing those wrongs

00:22:19.100 that he developed his reputation as a speaker and eventually became a politician and this

00:22:23.640 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.

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00:24:09.800 Yeah. Those are all great examples. Just so much you can learn from those people.

00:24:13.200 Was there one you liked?

00:24:14.440 Well, you know, of course I love Teddy Roosevelt.

00:24:16.520 Me too.

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

00:24:47.660 title. Wow.

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?

00:25:01.480 Yeah.

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 0.80

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 0.95

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.

00:41:32.940 And until next time, stay manly.

The Art of Manliness - April 26, 2014

#65： The Obstacle Is The Way With Ryan Holiday

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