Features: ‘The Obstacle is the Way’: Interview with Ryan Holiday

Ryan Holiday, author of The Obstacle is the Way (May, 2014)

Interview by Zach Obront

What jumps out to me about Stoicism is that while it’s become popular in a sense, it seems like the mainstream only sees the same couple of thoughts continuously reemerging, as if these were the core principles of the philosophy. When I first read straight from the source though, it struck me that Stoicism is much more like a collection of practices and exercises than a traditional philosophy. Do you agree that its focus is entirely practical?

So, what I like about Stoicism is that, historically, it was the philosophy for men (and, I’m saying men because it was only men then) of action. Leaders, generals, politicians, you know? For most of the later Stoics, the focus was very much of ethics or operating principles. And so, I see Stoicism as being adapted for people who do stuff in the world. Not college professors, but people who are leading soldiers into battle, running a government, representing the people, that sort of thing. So I think that, when you look at the exercises, you see all sorts of things that are supposed to be reminders or solutions to the problems that a person like that faces.

So whether it’s Marcus Aurelius or Seneca, their writings are reminders of the problems that you tend to bump into. So, you know, Marcus Aurelius reminds himself not to be stained by the robes that he wear, which is a way of saying, “Don’t let it go to your head.” Or, he’s talking about never being overhead complaining in court. He’s saying, “This is your duty. This is your job. Complain at home, but do your job when you’re doing your job.” Or Seneca, who writes this letter where he goes through this exercise where he says “I’m going on a trip. This is what I plan to do, but I’m also ready for things to go terribly wrong, and this is how I’m going to handle the plans going awry.”

I think all the exercises have a lot of implications for how to make you a better, more honest, virtuous person. But they also have the side effect of making you a more effective, efficient, dutiful, reasonable, rational leader or person of action. And so that’s what I tend to focus on in my reading and understanding of Stoicism.

I really like that. So, do you see that as possibly the reason why the practical side of Stoicism hasn’t had such a big influence on academia historically? Because, they’re really focussing on individual possible situations one at a time. You couldn’t summarize Stoicism in a couple of sentences whereas, with most major philosophies, you could. Maybe their specificity in dealing with problems is a reason why academics have shied away from them?

Totally. I think the real difference is that Stoicism has a totally different definition to the kind of person people normally think of as a ‘philosopher’. Again, although they have a metaphysics, they are much more interested in exercises that help people with the problems that they face in their daily lives. And, so, it’s almost like Yoga, in the sense that it’s a physical act, rather than a book that you read. Stoicism is a process of reminding yourself, thinking certain things, and checking your sometimes unhealthy natural instincts against a set of easy to remember assumptions and facts about the world.

But Stoicism still survives within normal, everyday people, whether you’re a soldier or a schoolteacher or someone who’s going through grief, and I think the reason is that Stoicism is accessible and designed for people. It’s not designed for college professors. That’s probably the real reason for it’s longevity.

I mean, I’m not the emperor of the world, and so I don’t totally relate to what Marcus Aurelius is saying. But I am trying to run my business, and there is an overlap there, and these spiritual exercises do work.

Absolutely. Okay, so let’s get a little bit more tactical then. Are there a handful of specific exercises that stand out to you and that you actually put into practice? I know you’re writing a book focused on one in particular.

Yeah, sure. So the book is called The Obstacle is the Way. And it’s basically a whole book about this one exercise. It boils down to the idea that, for a Stoic, there’s no such thing as adversity, because adversity is actually a chance to prove yourself, to try various virtues, to be creative. It’s the world testing you. Stoics say that events don’t come preloaded with good or bad meaning, there’s only perception. But this exercises goes even further, and it says that everything bad that happens to you is actually “a good”, as it’s an opportunity to try something that perhaps otherwise you wouldn’t have been able to try.

Another favourite exercise is the idea of contemptuous expression, which you see a lot in Marcus Aurelius. So, you take something, like “You’re sitting at a luxurious, sumptuous feast” and you explain to yourself what you’re actually seeing. So “Wine is fermented grapes, and there’s a roast which is just a dead pig that’s been burned, and there’s cheeses, which are just milk that’s been allowed to curdle.” So you’re reminding yourself of the reality of what’s in front of you. I mean, he describes sex as rubbing and then an explosion. Its just the idea of reminding yourself honestly what these things are. Not to get disgusted with them necessarily, but to remove that narrative power that we tend to put on things. And, look, when you’re the emperor of the world, you’ve got to be constantly combating the esteem and the power and the false meaning that everyone is projecting on things, because they’re trying to make you a god while you’re still alive. And our celebrity-driven, wealth-driven, narcissistic culture does that too. So I really like that exercise of really paring things down to their essence.

And then, of course, there’s the Stoic theme of the Art of Acquiescence, which is just getting better and more comfortable with accepting what happens to you. This is not fatalism, but kind of the opposite: love everything that happens to you, because you know you can handle it and you know that there’s nothing you can do about it. It’s that Serenity Prayer kind of mindset.

 Those are three of my favorites, if that answers your question.

Yeah. All of those are really insightful. It’s funny, coming back to the Obstacle is the Way, that even before I came in contact with Stoicism I made a conscious effort to train impulse control. So I really thought about every challenge as an opportunity to develop that skill. When I came across the idea as a more generalized Stoic principle, it made a lot of sense to me. I mean, if you’re consciously trying to improve yourself, clearly all those challenges are positives.

To dig a little deeper, do you have any advice in terms of how to actually apply these exercises? I think a lot of people read this stuff and it resonates with them and then they don’t take the next step to really bring it into their lives. What do you suggest?

I don’t think this can really be brought down to one paragraph or sentence, but the Turning the Obstacle Upside Down [another name for The Obstacle is the Way] requires three distinct phases or acts, that are all themed in Stoicism:

The first would be controlling your perception. So, it’s the idea that, the way that things appear, especially the first impressions, are notoriously unreliable. And that if you can maintain a cool head and a cool emotional state, at the very least you don’t make things worse. And at the very best you’re able to spot chinks in the armor, or a different way of doing things. There is no advantage to be gained from an instantaneous irrational emotional reaction. So that’s the first step, controlling your perception.

The second step is your actions, and your actions adhere to this code of duty and obligation and energy and creativity. So, second is how you orient yourself to act.

Then, third, there’s this idea of the will. Which is, first, your will power, but also, your understanding of your place in the universe. And the idea that, “Look, you don’t control everything that happens to you, you only control your reaction. And you’re going to die. Soon, perhaps.” And, so, that third phase is what puts it all into perspective.

So those are the three phases as I see them and, in the book, I sort of walk people through those phases.

I think that’s hugely important. Stoicism takes things a whole level of practicality past most philosophies, but it doesn’t quite take it to the tangible, actionable, what-do-I-do-when-I-wake-up-tomorrow-morning level. So I think a lot of people read it and resonate with the ideas, and then don’t actually act on them, even while saying, “It’s so awesome because you can act on it!”

Yeah, you know what? I think part of the problem, too, is when you get into some of these Stoicism communities, you get the people who are attracted to the philosophy for it’s anti-materialism and anti-ambition. These things are very important – about not being upset and chasing and whatever – and I totally respect it. But when someone who is in a position of influence, or success, or achievement, comes to these people and asks for advice, they never give you practical advice. And it’s like, “This is my life’s work, I’m not just going to throw it out the window.” So I think you’re better off taking the idea of how can Stoicism help, rather than how can Stoicism tell you to not be a human being.

Definitely. I love that. So, the last thing I want to touch on is the book. What’s your plan for it? Where can people get it? Is it going to be available in paperback?

Yeah, so it’s a full book. It’s published by Portfolio-Penguin, the same publisher as my first book. They’ve done everyone from Seth Godin to Steven Pressfield, so it’s a legitimate, prestigious publisher. They really like the book. The reality is that most people do not wake up in morning and say “I need philosophy.” For better or for worse, that’s not what people think. So I’ve tried to write a book that’s about helping them with their actual problems, that happens to rely on philosophy. The book is inspired and rooted in Stoicism, but it does not beat anyone over the head with it. Because, I think that the way you bring people into this way of thinking is by showing it’s practical benefits for them right now, with what they’re struggling with. I’m really writing a book about Stoicism for people who don’t think they care or want to know about Stoicism, so I’m kind of trying that Trojan Horse strategy.

So that’s the book, and it comes out in May 2014.

If you can get to the point where non-philosophers are recommending it as something that’s actually impacted them and changed their day-to-day lives, that has the potential to be really huge and make a big impact on the kind of people who would never discover this stuff otherwise.

Thanks so much for insights, Ryan. Looking forward to it.

Ryan Holiday is a media strategist for notorious clients like Tucker Max and Dov Charney. After dropping out of college at 19 to apprentice under the strategist Robert Greene, he went on to advise many bestselling authors and multi-platinum musicians. He is the Director of Marketing at American Apparel, where his work in advertising was internationally known. His strategies are used as case studies by Twitter, YouTube and Google and have been written about in AdAge, the New York Times, Gawker and Fast Company. His first book, Trust Me I’m Lying: Confessions of a Media Manipulator, was a Wall Street Journal bestseller. He currently lives in New Orleans with his rebellious puppy, Hanno.

Zach Obront runs a blog at http://zachobront.com, where he rambles about entrepreneurship, psychology and history. He’s also the founder of Landline Assassin, a telecommunications company leading the battle against home phones, and the head of recruitment at GiveGetWin, a growing non-profit dedicated to turning the philanthropy model on its head.

One thought on “Features: ‘The Obstacle is the Way’: Interview with Ryan Holiday

  1. Mark

    Good point to focus on the practicality of Stoicism in contract to much of the metaphysical abstractions we see in the continental philosophies of Derrida etc (reminds me of Sophistry). It’s also critical to understand the historical context of Stoicism and why the Roman political class adopted it. From the panoply of Greek thinkers only Stoicism really stuck with the elite of Rome. Sophistry, epicureanism and mystery cults were not conducive to conquering the known world. In the face of catastrophic military setbacks (e.g. Hannibal), the Romans adopted a “keep calm, carry on” attitude that was historically unprecedented. It’s no wonder then why Gibbon focused on the effects of a mystery cult in destroying a civilization.

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