The Obstacle is the Way: A Timeless System for Transforming Challenges into Opportunities

Life is hard. Really hard.

We’ve all had experiences that made us want to throw in the towel. Maybe you gained a ton of weight.

Maybe you binged during a diet.

Maybe you got injured.

Maybe you experienced something far worse, like getting fired, dumped, or losing a loved one.

Most people don’t deal with these situations well. They complain, worry, and make things worse.

You can do better. In this interview, you’ll learn how to use the ancient practice of stoicism to turn every challenge, disappointment, and obstacle into an opportunity to “express a virtue,” as our guest Ryan Holiday says.

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Show Notes

The Obstacle is the Way by Ryan Holiday

Trust Me, I’m Lying by Ryan Holiday

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### Transcript

**Armi Legge:** Life is tough. Sometimes it can be really tough. We’ve all had experiences that made us want to throw in the towel. Maybe you gained a bunch of weight. Maybe you binged during a diet. Maybe you got injured. Maybe you got dumped by your significant other. Or maybe something worse like losing a loved one or getting fired from your job.

Life can really suck sometimes and most people don’t deal with these situations well at all. They complain, they whine, and they don’t make things better. They view it as a completely negative situation.

Now you have probably met those people who say, “Oh, you should just look at everything glass is half full, there’s always a silver lining.” And you usually want to strangle those people because they’re just terribly annoying in the moment. And in truth, that is not very helpful, to just say, “oh, this is a positive experience” and try to move on. But there is a better way to manage these situations that can result in a positive outcome. And that’s what we’re going to talk about in this interview.

Ryan Holiday, a friend of mine and best-selling author and a former marketing consultant for companies like American Apparel and he also worked with Tim Ferris on on helping him market several of his books, is going to be on the podcast talking about stoicism and how you can apply that to turn every challenge, disappointment, and obstacle into an opportunity to “express a virtue,” as he says.

My name is Armi Legge, and you are listening to Evidence Radio, and podcast that helps you simplify your health and fitness so you can move onto more important things. Before we get started, if you want to keep up with everything that’s going on with, follow me on twitter @armilegge. Now let’s hear from Ryan Holiday.

Well, Ryan, thank you for coming on the show. Would you tell our listeners a little bit about yourself, who are you, and what you do? You come from a unique background compared to most people who have been on the show.

**Ryan Holiday:** Yeah, sure. I’m a writer and I guess a marketing and strategic consultant. I work with brands, startups, businesses. My clients include the New York Observer, American Apparel, best selling authors like Tim Ferris and Robert Green, who wrote “48 Laws of Power” and “the 40 Hour Work Week.”

Then I’m the author of three books myself. I wrote “Trust Me, I’m Lying,” which is an exposé of the modern media system. I wrote one called “Growth Hacker Marketing,” which is sort of about startup marketing. And then this one is called “The Obstacle Is The Way,” which is what I guess we’re going to talk about partly today.

**Armi Legge:** Exactly. So would you tell our listeners what your new book is about and how you got interested in writing about this topic?

**Ryan Holiday:** Yeah, sure. The new book takes a classical philosophy known as “stoicism,” which was popular with Greek and Roman elites around the turn of the millennium and it applies their strategies of sort of resilience and fortitude and discipline and it applies it to modern business problems. So I take a very specific stoic exercise that’s at the root of the book, it’s a passage by Marcus Aurelius about how, he says, “The impediment to action advances action and stands in the way and becomes the way.” It’s about how every problem or obstacle that we think that we face is actually an opportunity to advance and to improve and to display some virtue or skill.

I take that and I apply it to modern business problems and I illustrate it with stories from everyone from Steve Jobs to Amelia Earhart to John Rockefeller to Ulysses S. Grant, politicians, strategists, thinkers, athletes. I use those stories to illustrate how one inculcates an attitude where what other people think are bad things, they actually look at as advantages and opportunities.

**Armi Legge:** Excellent. Most of the people who listen to this show either want to get leaner or bigger or stronger. They want to pursue some kind of athletic goal and it sounds like you’ve written about athletes some, too, but before we get into that, if you could summarize the main concept of your book, what would it be? You talked about turning obstacles into something productive.

**Ryan Holiday:** I’ll give you an example from sports I talk about in the book. There was a recent, pretty fascinating study where they looked at a bunch of elite athletes in Canada who had just undergone some sort of major injury and they looked at the feelings that athlete felt at the time of injury. It was despair, they were doubting their talents, they felt disconnected from other athletes in their field.

And then they looked at them after the recovery of that injury and they actually felt the opposite of those three things afterward. They were more connected with their teammates. They felt stronger in their skills. They actually felt better. The psychological term for this is “adversarial growth” or “post-traumatic growth.”

The premise is instead of injuries being a bad thing over the long-term, they actually make us better in a lot of ways. So the book is about that sort of attitude across our lives. It’s like, look, we all know if you were to look at the three or four big failures in your life, you can see how you got better from those big failures and how your life is better as a result. You might not undo that failure if you were ever given a chance. If you could go back in time and never make that failure happen, you might actually pass on that opportunity.

And yet, in our lives, we deliberately avoid things that might subject us to failure. We run from things that are difficult and complain when shitty things happen to us when, in fact, the stoic attitude the book is about is really about how this is actually a good thing. It’s a gift.

**Armi Legge:** How would you say this differs from the common advice that we’ve all been told since we were little? “Just have a positive attitude.” How does it differ from that?

**Ryan Holiday:** One of the concepts in the book is a Latin term from Nietzsche, but it’s actually from the stoics. It’s where I got it. It’s called “amor fati.” It means loving fate, loving what happened to you. It’s very easy to look at something bad and just be like, “Wow! The glass is half full.”

But the example I used to demonstrate amor fati in the book was the story of Thomas Edison. He was in his 70s. He had just returned home for dinner. A frantic call comes in. His laboratory is on fire. It totally burned down. You would think this is the first thing ever, right? He rushes to the scene. His son is there. He says to his son, “Go get your mother and all her friends. They don’t want to miss this. They’ll never see a fire like this again.”

His whole life is on fire in front of him and he’s excited, almost overjoyed with enthusiasm. Afterward, he was interviewed. He’s like, “Look, I’m an old man. I’ve built up a lot of crap in my life. This is actually a chance to start over. I feel energized. I feel excited. I’m going to turn this whole thing around.”

Optimism is easy. Amor fati, like truly loving and embracing things that happen to you, truly terrible things, is I think another level of that and there’s a big difference between those two levels.

What I’m talking about is how we can see some of the worst things that can happen to us in life and of course everything that happens to us in life as an opportunity to exhibit some virtues. That’s very different from just pretending a bad situation is a good situation. It’s taking a bad situation and making it a good situation through your philosophical outlet and in the actions that you take as a result of it.

**Armi Legge:** Right. If you don’t mind, what are some examples of challenges you’ve faced where you’ve used this paradigm to get through?

**Ryan Holiday:** I get that question a lot and I kind of reject it because the idea that I need to prove this book with my own experience is not why I wrote it. These are timeless, historical precepts and observations that I’ve observed and I’m reporting on in the form of a book.

But of course, look, we all have terrible things that happen to us but people’s own sufferings and trials and travails are relative and subjective, so me telling you about the time I got dumped by this girl and I thought my life was going to end and then I thought about it differently and I’m better. That doesn’t inspire you or help you at all. I want to look at real examples from history where people faced unimaginable circumstances and instead of despairing the way I might have when I got dumped, they found a deep positive in it.

That’s why I’m looking at examples from the Civil War, from the Industrial Revolution, from pioneer days, from prison camps. I want to look at the times humans were most tested and they used that test to answer very much in the affirmative. Does that make sense?

**Armi Legge:** Absolutely. I think one way to summarize that would be most the problems that we face just aren’t that important like getting dumped for instance or being late for work, that kind of thing compared to your life’s work burning down or being in a concentration camp. Those are much better, more enlightening examples it sounds like you’re saying.

**Ryan Holiday:** Of course. At the same time, when someone calls you and they’re a dick to you on the phone and you want to punch them in the face, you use those examples to give you perspective and to remember that if they could do it then, you can do it now. I think that’s really the problem and that’s why I wanted to write the book.

Life is always difficult and it will always be difficult, but when you could die from a tiny cut on your finger or from cholera or from any other number of unpredictable, awful things, from warfare, from genocide, from these terrible circumstances outside our control, people had a framework for dealing with suffering and with difficulty and with misfortune. That’s why most of the examples in the book are old.

The problem is we live in some of the most prosperous times in history and then we have a small economic dip and people who are our age are screwed, right? They have no idea what to do. Someone might feel– like someone like you, knowing your story, you dropped out of high school, right? Your life, just by nature of what it has been, I think gives you a perspective that makes it easier for you to deal with adversity and to deal with difficulty than someone who hasn’t been tested and who has had an easier past.

What we have to realize is that most people out there have a much easier path than our predecessors in history and that’s why they’re so ill equipped to deal with uncertainty and difficulty and the problems that we face right now.

**Armi Legge:** Sure. What is perhaps your favorite example from the book that you at least remember on a daily basis, that you can refer to for any experience?

**Ryan Holiday:** I mean there are so many. These are the stories that I’ve read and thought of so often in my life. If we want to talk athletics, one of my favorite ones is the story of Theodore Roosevelt, who I think people understand as this picture of masculinity, health, and vibrancy, was born as a frail and sickly kid who was crippled with camera up until he was 12 or 13 years old, like a debilitating, crippling asthma. His parents would wake up and think he was going to die that night.

One day, at the prompting of his father, he was given a challenge. He was like, “Look, you have a brilliant mind but you have a weak body and a weak body doesn’t do a strong mind justice. You have to fix that problem. It’s all on you. You didn’t cause it but it’s on you to fix.” There’s this famous line that he said. Theodore Roosevelt’s sister actually witnessed it. He said, “I will make my body.”

You can actually visit the house where he did this. It’s still there in New York City and see the porch where his father built him this gym. He basically more or less worked asthma out of his system, which as far as I know isn’t exactly possible but somehow he did it with sheer sorta force and energy. He took an unfortunate situation and used it as a springboard to become the face of American energy and ingenuity and outdoorsmen and adventure. It’s what propelled him to the greatness that he eventually achieved.

That story is a common one in the book. I tell the story of Democedes who was a great Roman orator who was born with a stutter and a frail body and worked that all out of his system.

I like this idea of people who are given one set of circumstances and decide that they don’t want it anymore and they work themselves to the opposite out of inconceivable energy.

**Armi Legge:** It’s an interesting perspective talking about Theodore Roosevelt. It seems like the people who experience the most adversity are often the people who end up going to that extreme. If you look at most bodybuilders, it’s just ridiculous how many of them were fat kids growing up and now they’re just huge and look great.

I alluded this to a second ago. Do you think that lack of adversity could be a negative in the long-term for most people?

**Ryan Holiday:** Malcolm Gladwell actually talks about this in his new book. He was talking about some of the studies that show the surprising amount of success that people who suffer dyslexia go on to have. We don’t really know why. It’s just a fact that people have dyslexia are overrepresented in things like the Fortune 500 and as authors or speakers or actors or doctors.

He asked a handful of these very successful dyslexics if they would wish dyslexia on their child. It’s like, “Hey, you have dyslexia. Now you’re worth $500 million. We think there is some sort of causal link between those two. You’re happy and successful. Would you want your child to go through what you went though?” The men were aghast at this suggestion.

That’s sort of the paradox, which is adversity and terrible and awful but it also makes us who we are, which is why I think stoicism is helpful. It’s a system for dealing with things that we don’t control.

Everyone faces their own adversity. Everyone is put into situations that they wish they weren’t in and the stoic framework I’m talking about in the book is what shows you what to do with that. It’s not about going out and seeking adversity. There’s no benefit in that. It’s about taking the cards they you specifically have been dealt and getting the most out of those cards. Some people get dealt worse cards. Some people get dealt better cards. You’re better off not thinking about their cards and focusing on yours.

**Armi Legge:** I think that’s an excellent way to finish this up. Ryan, thank you for sharing your knowledge and telling people about your new book. Where can people learn more about what you’re doing and where can they sign up to be notified when the book is ready?

**Ryan Holiday:** Yeah, of course. So the book is out May 1st. It’s available on Amazon, bookstores, it’s already published in a few languages so it should be available just about anywhere. My website is You can follow me on twitter, it’s just my name. If you have questions or you want to learn more about stoicism, you can email me. It’s just

**Armi Legge:** Right. And Ryan also has an excellent newsletter where he shares some of his book recommendations as well, which you should definitely sign up for.

**Ryan Holiday:** Awesome. Thanks, man. I appreciate that.

**Armi Legge:** Thank you for being on the show, Ryan.

**Ryan Holiday:** Yeah, of course!

**Armi Legge:** If you enjoyed this interview or just like hearing us talk, first please check out Ryan’s new book. I read all of his previous book and he is an outstanding writer. Even if you are not really that interested in this topic, you should read it anyway. Get out a highlighter and go through it.

Second, if you enjoyed this interview, you should also leave a review and ranking on iTunes.

And finally, I want you to apply this information today. I want you to think of one thing that really sucks right now in your life. One thing that is just driving you nuts. Apply what Ryan Holiday talked about today in this interview to that situation.

For instance, for me right now, I have had an extremely hard time getting my work done. I don’t want to do it. I’m procrastinating and I’m being kind of a little bitch about it, honestly. And it’s not helping it.

Now I can look at that and see myself as a failure and be hard of myself, which is frankly what I’ve been doing, or I can look at it as an opportunity to refine my productivity system, to branch out into some other projects that I haven’t really been working on that much.

For instance, I have started a new podcast, which you have probably heard about in previous episodes, called “A Real Model” podcast with a friend of mind, which is something I know nothing about but it’s something that keeps me interested and motivated. So there is always a way you can spin a situation in order to express a virtue instead of letting it destroy your life, which is what I usually do and you probably do, too, sometimes if you’re like me.

So think about that. Think about a situation that is driving you nuts right now, that’s really hurting your life, and apply what Ryan Holiday talked about. Thank you and I will talk to you next week.

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