From American Apparel To Stoic Philosophy: An Interview With Ryan Holiday

There are few people that I look up to in life, and Ryan Holiday is one of them.  After dropping out of college at 19, Ryan served as the Director of Marketing for American Apparel, advised authors like Tucker Max (I Hope They Serve Beer in Hell) and Robert Greene (The 48 Laws of Power), and wrote a controversial, bestselling book about his experiences, Trust Me: I’m Lying: Confessions of a Media Manipulator.

Ryan recently released his new book, The Obstacle Is The Way, which is based on Stoic philosophy. It’s centered around the principle that every obstacle in one’s life can be turned into an advantage, and it’s decorated with real-life examples that show how mastering Stoicism is like gaining a mental superpower. If you feel that something—family, tragedy, genes, addiction, etc—is holding you back in life, I recommend this book.

I recently interviewed Ryan. Here is our correspondence.

Thought Catalog: What motivates you to be successful in life?

Ryan Holiday: Trying to be successful isn’t exactly a goal or a motivation. I always wanted to be a writer—books specifically—but when I looked at other writers I admired I realized that they’d had these amazing, interesting lives. So I went out and tried to live that. It drew me to business and marketing and unusual controversial people and that made me successful (financially at least) and then put me in a position to write books and have something to say.

But to say: I am successful at life, what does that mean anyway? That you have money? That you get to work on the projects you want? That you have a family? That you do cool stuff? We all have our own definitions, I suppose.

TC: When you were growing up, what were some things you wanted to be?

RH: I don’t recall wanting to be anything really except maybe a musician until I decided I wanted to be a writer. For me it’s more like: oh, I have an opportunity to try to get good at this thing? And there’s a chance I could get paid for my time? Ok I’m down. It’s worked out well.

TC: What was high school like for you?

RH: You know it was hit or miss. I had some teachers who hated me and I couldn’t stand and they thought I was a problem. And I had other teachers who nurtured me and made me feel like I could really do something. I had close friends but I also felt isolated and misunderstood. Typical I’m sure for most teenagers, especially teenage dudes. I was just happy to get out of there.

I thought college was going to be this amazing place where all that went away, but of course it wasn’t. So then I was so ready to get out of there. The irony now of course is that you look at those things and see what you didn’t appreciate.

TC: You’ve written recently about lacking the pathology of certain hyper-successful people, and being grateful for that. Can you talk a little bit about that?

RH: Anyone who has ever worked with a billionaire or a celebrity or an artist of some type can usually tell you, they are amazing but they are also nuts. There is usually some sort of drive, I don’t want to say it’s a part of them that’s broken because clearly it’s adaptive but still, they are compelled in a way that most of us aren’t. Dr. Drew did a really interesting study on celebrity a few years ago and basically found that yes, being famous makes you more narcissistic but really it’s narcissistic traits that drives people to become famous. It’s the same thing with hyper-successful people. It’s not always narcissism but it’s something, and what it is depends on who they are and what they’re doing.

TC: How have your goals and ambition changed since you were 19?

RH: Haha, one of the things I struggle with—in a very grateful way—is that this was about as far in advance as I thought.

TC: What is your next career move? What type of books do you plan to write in the future?

RH: I don’t want to say more of the same because that sounds bad. But I want to be able to carve out a niche for myself writing books that no one else could write. That are mine and mine alone and that help people with their problems, that help me with my problems.

TC: Do you pay attention to style when you write? If so, who are your biggest stylistic influences?

RH: You can’t. You have to write what feels natural. But I always try to base my books on books that I deeply admire. Trust Me I’m Lying was inspired by The Brass Check by Upton Sinclair. The Obstacle Is The Way was part 48 Laws of Power, part The War of Art.

TC: Have you ever written fiction, even as a hobby? If so, could you describe something you have written?

RH: Nope, never. Beware of people writing fiction as a hobby.

TC: What is one trait that you would still like to improve on in life?

RH: Calming the fuck down and passing on getting involved in things.

TC: What is one trait that you think has separated you from your peers and allowed you to achieve the success you’ve had?

RH: Intensity. Balanced by sanity.

TC: What is your biggest regret?

RH: Thankfully nothing I talk about publicly.

TC: If you could have been born in a different time period and/or country, what time period/where?

RH: US, old enough to serve in the Civil War but not as cannon fodder. It’s also if you look at it, the time which minted most of the richest men who ever lived.

TC: In your book, you talk about the importance of compassion for others. What motivates you to be a good person?

RH: If you need motivation you’re doing it wrong. The only self-interest required is the fact that terrible people are usually miserable people.

If you’re interested in reading free Ryan Holiday work, you can see what he’s written for this site here. You can also order his new book on Amazon.