Interview - The Obstacle Is the Way with Ryan Holiday

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Hi, this is Brian. Welcome back to the Optimal Living Interview series. Today, I'm thrilled to be with Ryan Holiday. Ryan wrote the Obstacle is the the Timeless Art of Turning Trials into Triumphs. And not only is it one of my favorite books of 2015, and I've read 75 already so far this year, it's one of my favorite books ever. It's just extraordinary. I was telling Ryan before we hopped on that got it at a perfect time for me as I was making huge shifts in our business. Alexandra loved the book and Ryan's work recommended it, and it's just a really, really good book. Ryan's an extraordinary writer, and he's able to pack in some inspiring classic wisdom in a really, really fun, inspiring, and super practical way. Ryan, thanks for taking the time. I'm excited to explore some of my favorite big ideas.

Yeah, thank you. You're very kind.

Well, it's all well earned. Let's just start with what do you mean when you say the obstacle is the way?

Yeah, so I don't know if it's necessarily something. I mean, if only because I took this from someone that's sort of much smarter and wiser than me, but it comes from ancient wisdom. I found it sort of specifically through Stoic philosophy. There's a line in Marcus Aurelius Meditation where he says, the impediment to action advances action. What stands in the way becomes the way. One of my favorite writers, he's now deceased. His name is Pierre Hadou. He was a sort of French philosopher. He called this when he was studying Stoicism. He described that language or that exercise as the exercise of turning obstacles upside down. It's this idea in Stoicism that everything that you face, good or bad, is a chance to practice a virtue. You and I are talking. We might have technical difficulties. I could get angry. That would be not a virtue. Or I could be patient and that would be a virtue. It's this idea of seeing all the things that you face as opportunities to practice the Stoic arts. Then it just also happens. There's a Zen saying or epigram that is the obstacle is the path, and sort of combine those two things together to create the title of the book, the Obstacle is the Way.

Right on. Already so much. We can go with that, but we'll talk about the top three aspects of embracing and actually turning our obstacles upside down. You basically organized the book around perception, action, and will. I'd like to Walk you through each of those and have you walk us through each of those. But let's start with perception. What does that mean? Why is it important?

Sure. So those disciplines are again, disciplines in stoicism that I think, obviously there's more discipline, there are more disciplines than those three, but those are the three that matter. If you're trying to take some seemingly negative thing and turn it into a positive thing, but it begins with seeing that thing as it actually is. And one of the things you see the stoics talk about over and over and over again, almost ad nauseam, it's this idea of they say there is no good or bad. There's only perception. There is our impression of things, and then there's the things as they actually are. And the Stokes would say, we take something that happens that is objective, and then we say that it's good, or we say that it is bad. And that's problematic because we don't control what happens to us. And so what they really urge the students to think about and talk about is to look at how our perceptions might make things harder for us. You lose your job and you tell yourself, this is the worst thing ever, you're going to starve to death. That's going to make it considerably harder than if you told yourself, I didn't like that job to begin with. Now I am free. The decision has been made for me that I am going to pursue this other thing instead. It's the way that we look at these things. And obviously there's lots of different ways to do it, but I focus on examples in history where people took things that any normal person might think were the worst thing that could have possibly happened and managed to see some good or some benefit inside of it.

That's awesome. Give us one of your favorite examples.

You know, I didn't talk about this last week, but I think Eisenhower, shortly after D day, so almost 71 years to the day from today, he launches this successful invasion. But then there's this massive Nazi counter offensive. Hitler basically ordered his troops to launch a massive panzer attack despite sort of any. Any reasonable strategy or a clear thinking to the contrary. But it was really bad, Right? It's a blitzkrieg of something like 200,000 Nazi troops. And if you've just launched an amphibious invasion, there's nowhere for you to go. You can't get back in your boats and go home. Right. And there's this magnificent scene, sort of Eisenhower, he walks in and he says, you know, he calls all his generals into this meeting and he's like, the present situation is to be regarded as one of opportunity for us and not disaster. There will be only cheerful faces at this conference table. And, you know, he's not delusional, right? He's a very logical guy. What he realizes is that this counteroffensive is, in fact, a massive opportunity, because if they can envelop these troops, it will essentially be the end of the Nazi army. It will be such a massive blow for them that they won't be able to do anything about it. And so it's. Instead of being overwhelmed, instead of freaking out, it's deciding, obviously, you would rather this not happen. You'd rather you just be able to march unopposed all the way to Berlin. But it's in seeing, okay, this is what we're facing, how are we going to make the most of it? That is the sort of stoic idea. Because again, what the stoics say over and over again is you don't control what happens to you. You control what you tell yourself about what happened. And then obviously leading into the next discipline, you control what you do about it.

Yeah, let's go there. So perception, incredibly stated, had goosebumps as you were sharing the Eisenhower story. That was awesome. Tell us about action. Discipline to action, right?

So stoicism is not the secret. It's not Eisenhower magically wanting this thing to be positive, and then it becomes a positive. It's what does he do about it? So first he sees it, first he sees a clue, then he gets off his ass and does something about it. One of the stories I tell, and there was a. I got a surprising reaction to this recently, but I love the story of Amelia Earhart. I sort of opened this section with that story. She can't make it as a female pilot. Sexism, bad economy, et cetera, et cetera. So she gets a call one day. This philanthropist is offered to sponsor a female flight across the Atlantic, but it's got a bunch of conditions that are admittedly regressive and ridiculous. She might be in the plane, but she's not allowed to fly it. She has to sit in the back. She's not going to get paid. The other people are going to get paid. She's basically a token woman on this flight. What I say is, okay, what do you think her response was? You think, considering what you know of Emilia Earhart, her response was, screw you, I'm gonna do it on my own. But that's not what she says. She says, yes, she does the flight. She's very honest about her minimal role in it. But she becomes a celebrity regardless. And shortly thereafter, she's able to fund and do her own solo transatlantic flight. And so, so often people think the obstacle is sexism or racism or whatever forces are aligned. And that is a big part of. But also one of the obstacles, I think, is our own ego, our own sense of idealism, sometimes that we want things to be a different way than they actually are. What I was so impressed with someone like Amelia Earhart is that she's able to sort of say, I need to get my foot in the door. Here's what I'm going to do. Here's what I'm willing to put up with, because I've got this larger goal in mind. There's this great line from Marcus Aurelius where he's like, there's brambles in the path. Go around. The cucumber is bitter. Throw it out. You do what you gotta do. And that's what I talk about. As a millennial, I watched my generation graduate into the financial recession, and I watched, like, half of them go, okay, I guess we're moving back home with mom and dad, because they wouldn't take a crappy job somewhere. They wouldn't start at the bottom. They wouldn't put up with stuff that they shouldn't have had to put up with. And the result is they lost several years of their life. I think that's very different than what something like Amelia Earhart did.

Wow. Again, so good and so much we can talk about there. We'll come back to that a little bit with some other ideas, but let's march from perception through action to will. So tell us about the third discipline.

So the perception and will are similar, but I think there's a critical difference. But it's the idea of, okay, if perception is about seeing things for what they are, action is about making the most of those situations. What. What do you do when there's nothing you can do about something? I tell the story of Thomas Edison. He's 67 years old. His factory catches on fire. He rushes to the scene. His son is there. He's distraught. Edison, he says to him. He's like, look, calm down. Go get your mother. Go get her friends. We're never going to see a fire like this again. It's not like he lost his mind. What he's thinking is like, look, factory's on fire. Nothing I can do about it. This is still pretty, serenely beautiful and awesome. Let's enjoy it, and then let's get back to work. The next day. And he tells a reporter, look, there was just a bunch of trash in there. I'm gonna be fine. He says, I've been through worse things than this before. It prevents an old man from being complacent, essentially. And he decides that what happened is. Is going to be invigorating. He's exhibiting an attitude that the stoics called amor fati or a love of fate. It's this sort of gracious acceptance of every single thing that happens to you. I'll give you an example. I was supposed to do this one speaking engagement in July, and so I said yes then. Because I said yes. I just found out today the decision is going to cost me a lot of money. I said yes too early. And so now I have to say no to this other thing that I'd rather do. Now. I could fight and claw and get all upset about this. I could blame my speaking agent. I could blame myself. I could try to get out of it. I could do any number of these things, or I could say, you know what? It's for the best. Going to make the most of it. Hopefully something really positive will come out of this. Something I'm not even able to think about or anticipate will be the result of this. We tend to think that what makes great people great is their willingness to fight for what they want. And it is. But it's also the ability not to sort of cry over spilt milk. Right. It's the ability to move on from things very quickly and focus on what they do. Control. And. And that's where this discipline of the will, I think, comes in, most importantly.

Yeah, that's so good. You have a great quote in the book. You say, if perception and action were the disciplines of the mind and the body, then will is the discipline of the heart and soul. I love that.

Yeah. Yeah, I think so. It's. You know, Martin Luther King was talking about this. It's this idea of like, we're going to fight, you know, power with soul power. He was like, what they're going to try to handle with force and aggression and will, we're just going to handle with love and acceptance. We have that gracious tolerance, acceptance, forgiveness in us, but so often we think that it's antithetical to ambition, it's antithetical to accomplishment, But I'm not sure that that's the case.

Yeah, that's awesome. Well, we'll kind of come back around to that. So now that we've laid the high level framework, perception, action, Will, I want to hear your thoughts on a few of my favorite big ideas. The next one is one of the. The way you wrote this story. It's one of the best stories I've read. The Panic Button and John Glenn. Can you tell us about that?

Yeah, it's interesting. We tend to think that what makes an astronaut or a fighter pilot so great is their big swinging balls and their aggression and all this stuff. And really what you find when you study the first Apollo program is what they were training over and over and over again is their ability to remain calm in crappy situations, their ability to, to regulate their emotions. John Glenn circled the Earth several times. His heart rate Never went above 110. Meanwhile, you miss a phone call and your heart rate starts racing or you drop a glass in the kitchen and you feel like you're gonna have a heart attack. And there's this great quote from that one astronaut. What is it? Chris Hadfield, where he's saying, he's like, there's no problem in space that humans can't make worse. That's sort of the idea that we've got to get past.

I love it. And you made the point that the first thing that they trained all these astronauts was just how not to panic. Right, right. That going nuts in space isn't an adequate solution to it. That's awesome. So 110 beats per minute while he's orbiting the Earth. And, and as you say, our heart jumps out of our chest the moment anything goes wrong. It's a good practice discipline. Tell us about post traumatic growth vis a vis post traumatic stress.

Yeah. So one of the things psychologists have found is that you tend to think an athlete never wants to get injured and nobody ever wants to feel pain or whatever. And it's totally true. But oftentimes when you study what you thought was some sort of career ending injury, the athlete actually comes back better. They come back more aligned with their teammates, they've thought about the game more, they're more in tune with their own abilities. They call this post traumatic growth, that when something bad happens, we actually bounce back. I talk about Tommy John, the baseball pitcher in the book a little bit. You know, he was one of the first pitchers to blow out their arm after, you know, almost 10 seasons, something like that. He ends up getting this surgery where they take the tendon in one arm, put it in the other. He comes back, he's a better pitcher than he was before. And now they call this Tommy John surgery. But basically it's this idea of like, we think that any sort of adversity or failure is going to be horrible. And of course, I guess it would be preferred not to have. But depending on how we respond, depending on what we learn from that thing, it might actually be good. It's funny, when you ask people, what I'll say is, look, what was the worst thing that ever happened to you? And how has that put you on the path that you're on today? Usually those people would not trade what happened if they could. It's obviously different when we're talking about the death of a loved one because we always want that person back. But it's like, oh, I failed out of college, or, oh, my first company went out of business, or, oh, I got dumped by my girlfriend, or whatever it is, and it turns out that they would not be who they are today without that thing. And yet we try our damnedest to prevent anything like that from ever happening to us.

Amazing. I love how Maslow talks about that as well. Right. That the key, one of the cornerstones of actualizing among these people he studied was the fact that they responded to these tragedies with exactly what you're describing. Right.

Yeah. Or Viktor Frankl says, like, you know, the ability to find meaning in our suffering is critical to human happiness because there is no such thing as no suffering. So if you can make the most of the suffering you do face, that's going to be far better than attempting to get really, really lucky.

Yep. Good stuff. All right, well, the next big idea, I called the equation for genius. You talk about purpose plus focus plus desire, unity of purpose, deafness to doubt, and desire to stay at it. And you share the stories of Grant and Edison. Can you talk to us about either one of them? But Grant, I think the way you described his victories was fantastic.

Yeah. So we tend to think of Grant as this loser president. Maybe he was an alcoholic, maybe he wasn't, but really, he won the Civil War. And he won it not because he was some strategic genius. In fact, the strategic genius in the war was George McClellan, who arguably was the. He was an on paper genius, had all the credentials. He studied war in France. He was. He was fantastic. Except he was also probably the worst Union general because he was so convinced that he had to come up with this great idea. He had to come up with this way to outthink the enemy. And he would never actually, like, you know, the rubber never met the road. And Grant took Vicksburg, which is arguably a much more important victory than Gettysburg, but Grant took it. It's a multi month campaign. He, he tried every single thing you could think of. He tried to reroute the river, he tried to go around, he tried to attack head on. He tried all this stuff and it didn't work. He ends up. He cuts his supply lines, he marches way down below. He ignores Vicksburg. He takes the capital at Jackson, Mississippi first. Then he marches back towards Vicksburg, takes this thing that was a fortress, an immense obstacle, turns it to his advantage. When you lay siege to a fortress, all of a sudden it's the people who are inside who are screwed, not the people on the outside. And ultimately he takes Vicksburg. It opens up the trade on the Mississippi. It's a critical victory. But it was really in trying all this different stuff, it was in cutting the supply lines, he sort of accidentally discovers the way that they end up winning the Civil War. It's how Sherman's march to the sea comes about. It's where the momentum in the war comes from. All of it. Because he didn't give up. We tend to think that genius is this sort of flash or epiphany, that we think that the invention of the light bulb is this great metaphor, right? It's like, oh, the light bulb going up above your head. In reality, the idea for the light bulb was not the hard part. It's the fact that Edison tried something like 6,000 different filaments one by one, until he finally found one that could last long enough to hold light for a number of hours that a customer would actually purchase. There was lots of filaments that would last for 20 minutes or even 10 hours. But the way you get a light bulb that is a commercially successful product, it has to be viable. It was his willingness to try every single day, 6,000 of these different filaments until one worked. That's the genius.

So good. Amen. Preach it. This is so good. The idea of kind of the fixed mindset. You either have it or you don't. And that flash of insight vis a vis. No, it's, are you willing to put in the effort again and again and again and again and again? That's your recipe. Unity of purpose.

Yeah. Edison has this line. He says, first you have your flash of insight, then he says, and then difficulties arise. Right? And that's how it works. Then the difficulties arise. And. And what sets a person who has a good idea to a person who has a successful invention is the ability to overcome those difficulties.

So good. And again, when we make the obstacle the way we anticipate those we apply proper perception, take the action, and then keep on fighting when we don't. Can't see the path through.

Yeah, exactly, exactly. And we understand that the very. If there was no other benefit from this process, it's that it's at least weeding out the other people who are fainter hearted than us.

Well, and you just use the phrase. Which is what I wanted to talk about next, the process. So you share a story about Nick Saban. Tell us about the process.

Yeah, so the process is, you know, you think that a great coach wins because they envision all the way to the end. You know, they've known from day one that they're going to win a Super bowl or a title or a bowl game or whatever, or they've got this sweeping plan for victory. But really a great coach is, you know, John Wooden was the same way. He didn't have extensive game plans. He practiced his team really well and then he told him to go out and do their damn jobs. Right. For Saban, it's like, look, don't think about all four downs. Don't think about the first quarter. Don't think about all four quarters. Don't think about winning this game or that game. Think about doing your job well right now, right this second. So that's finishing a tackle, finishing a drill in practice, putting on your uniform. Right. Winning the kickoff, whatever it is. He's trying to break it down into its smallest component part and understanding that the process is doing each one of those parts really, really well.

It's brilliant. And you do that with proper level of attention and the outcomes will take care of themselves.

Yes, yes, exactly. Bill Walsh, he says, he used to say the score will take care of its. And that's really the idea. If you do everything else well, the score is going to be a reflection of that. And if it's not, it wasn't really your game to win to begin with.

So good. This is solid stuff. A ton packed in so far. What have we not talked about that you think we should talk about?

I'm trying to think. One of my favorite parts in the book is the more morbid part. But I talk about this idea of meditating on your own mortality. I think we tend as entrepreneurs to think it's like, oh, I got to build this legacy. I got to live forever, I got to be famous. I got to do all this stuff. And really it's like, look, you could die tomorrow. I could die five minutes from now. What matters, and this is why the process comes in, is the result is never guaranteed.

Right.

You're not guaranteed to live until you're 80. You're not guaranteed that the economy is going to survive forever. All you're guaranteed is the process itself and everything that you do. And so the less sort of pretentious you can be about some of that stuff, I think the better and more focused on the present you can really be.

I agree. So tell us about that. I love the way the stoics practice that in rehearsing your death. But give us.

They call it meditating on your mortality. It's this idea of, they say, let death be on your lips. Never lose sight of the fact that you're on this planet for a very brief amount of time and that as soon as you're dead, you're dead. And you don't get to take anything with you that sort of urges you to think about doing the right things for the right reasons. Right now.

That's good. Well, that was an awesome quick tour through.

Awesome.

Some deep wisdom there. Let's step back and tell us about what you do. So one of the things that I do a lot in my work is to help people identify the fundamentals, the things that they do consistently that help them reach their own levels of optimization and actualization. And the idea is great. People differ in what they do in terms of expression, but they share a common commitment to whatever their fundamentals are. So I'd just love to hear what you've kind of arrived at and what works for you, if you would be open to sharing that.

Yeah. I mean, so obviously stoicism is what I do. It's what I think about. It's different for me as a writer. Right. Like, if I hadn't written this book, I'd be writing this in a journal every day and reminding myself it's nice and it's a little bit synergistic that I get to write it in a book and then sell it to people. But it's weird and it might sound pretentious, but it's like I use my own book and I. Sometimes I write these things to hold myself accountable. What Stoicism is what people have got to remind themselves. Stoicism is not like, okay, this is the Bible telling you how God is and how the world is. Stoicism is a series of exercises. So it's not about, okay, you heard me talk about meditating on your mortality. And you're like, oh, yeah, that's true. And then that's it. It's like, no, you actually have to do it. You have to think about it on a regular basis. It's not amor fati or it's remembering to see the opportunity inside the obstacle. It's like something bad happened. Okay, what good can I make from this? And reminding yourself of this on a constant, regular basis. These are not sort of words from on high. These are sort of practical suggestions from people who have been through things that are far worse or far more stressful than whatever you and I are going through.

Love it. Right on. All right, well, the last question I'd like to ask is, if you could only share one piece of wisdom, one big idea, what would that be?

I don't know. I don't think there's some magic, you know, magic bullet. I don't think there's some magic thing. I think the idea of the obstacle being the way is a big one. I try to think about all the time how I can take whatever I'm doing and get something out of it, how to make the most of this thing. I think a formula for stoic optimism. But there's other things. There's other virtues that are more important. It's not just about doing, doing, doing. And I think at different times in our life, we need different things. I don't have an easy answer for you, but I would say that what I feel like my job as a writer is and what I feel like my purpose as a person is to articulate and think about these things and try to communicate them with people. That's what gets me up in the morning.

I think that's genius. The big wisdom is there is no one hydraulic.

There's not a magic solution that will make you feel good all the time and will make things not suck.

Come on, don't tell me. Don't burst my bubble on that one.

Right, Right. There's just work and there's just thinking and there's just pushing yourself and trying to be a better person. That's all there is.

Well said. As I've already said a number of times in our chat, the obstacle is way awesome book, Ryan. Where can people learn more about you? And what else do you have going on that you think they might want to hear about?

So my website's ryanholiday.net I have a reading list email where I suggest books every month that they can check out on my site. And I'm working on more books, and I hope people keep reading them.

Right on. Well, I can't wait to get the next ones in line. And once again, thank you for your commitment to all this wisdom and appreciate you taking the time.

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