Interview: Ryan Holiday

Interview with Ryan Holiday for Stoic Week.

Ryan HolidayQ: How would you introduce yourself and your work to our readers?

It’s funny, introducing myself is probably my least favorite thing to do. I’ve always been an introvert and so one of the reasons I’ve always liked writing is that I don’t have to do that very often—I just say what I think or know and people take it or leave. Usually at parties, I introduce myself as “My name is Ryan and I am a writer,” and since most people assume writers are basically starving artist, that usually wraps up that part of the conversation and then we can talk about normal things and not work. The slightly longer answer is that I am an author who has written five books, three about practical philosophy and two about marketing and media. The latter due came out of my career as the director of marketing for American Apparel and my work with a number of other authors and public figures. My books on philosophy, The Obstacle is the Way, Ego is the Enemy and now, The Daily Stoic came out of my love of philosophy and history. They are filled with stories and advice for people who are trying to achieve things, solve problems and find their version of the good life.

Q: How do you currently makes use of Stoicism in your work?

I say that my books are books that feature stoicism as opposed to being works of Stoicism. I think it’s incredibly hard to add something new to the canon of ancient philosophy as a modern person. There is room to translate, extrapolate and illustrate—and that’s what I did in The Obstacle is the Way I took a single stoic exercise from Marcus Aurelius and built a book of inspiring historical stories around it. As a executive and an entrepreneur, Stoicism is also a part of my life. Something goes wrong—how do I respond? Stoicism is there. I have to make an ethical decision, I want to try to think about the Stoic definition of virtue. If I’m experiencing success—material or otherwise—well, what do the Stoics say about how to handle that. None of that is to say that I am perfect in my application (in writing or in life) but I try and I think I’m getting better the longer I do it.

Q: When and how did you first become interested in Stoicism?

I was 19 years old and I attended a conference with the radio and television host Dr. Drew Pinsky. I asked him for a book recommendation and he put me onto the Stoics. To say that recommendation changed my life does not go far enough. It has in fact directed the entire course of my life. Marcus Aurelius was what Tyler Cowen calls a “quake book” for me. It shook everything I knew about the world. I’ve since turned to it hundreds of times—good times and bad times—and consulted it in my most difficult moments. After Marcus, I fell in love with Seneca and then Epictetus. Then I moved on to Pierre Hadot. I believe I found your work and the connection to CBT shortly after that. It’s been a ten year journey now, and I still feel like I am at the very beginning of it. The books don’t change, but like Marcus quoted from Heraclitus reading them is like stepping into a river. We are not the same and they are not same because of it.

Q: What’s the most important aspect of Stoicism to you?

There’s a line that I like in Hays’s translation of Marcus Aurelius that I think sums up Stoicism and that I use as a good summary of the idea. I can actually type it from memory, here:

Objective judgement, now at this very moment,
Unselfish action, now at this very moment,
Willing acceptance, now at this very moment, of all external events.
That is all you need.

To me that captures the three disciplines (perception, action, will) very nicely. It tells you how to see the world, how to act in the world, and how to come to terms with the world. It is indeed all one needs. You could spend a lifetime trying to just live that quote.

Q: In what ways do you think Stoicism still matters today?

Well, look we’re in a resurgence of Stoicism precisely because it does matter today. The reason that its found resonance with entrepreneurs and athletes alike is because not only are we in tumultuous times, but like the days of the Romans, many of us ‘stand alone in the universe.” What I mean is that with the decline of religion, even a decline in ideas like patriotism, leaves a vacuum. How should one life? What metric should they judge their decisions by? What matters? What doesn’t? These are questions that Stoicism helps answer. Or at least, they help me answer.

Q: How has Stoicism affected the way you live your life?

Like I said, Stoicism has helped me professionally and personally. I’m somewhat unique in that I also partly make my living studying and writing and speaking about this philosophy. I feel very lucky in that regard—because I would be doing it anyway. In any case, it is rare that a day goes by that I don’t think of some Stoic precept or idea.

Q: What’s one of your favourite Stoic quotations and why?

A different times in my life I have loved different parts of Stoicism, but right now I really love this line from Marcus: “To accept without arrogance, to let it go with indifference.” We translated it in even pithier form in The Daily Stoic: “Receive without pride, let go without attachment.” To me it’s one of those perfect expressions like “And this too shall pass.” It’s a recipe for any and every situation. It makes you better in good times, stronger in bad times.

Q: What advice would you give someone wanted to learn more about Stoicism?

I usually tell them to start with the originals. Don’t read about Stoicism, read the Stoics. I think Marcus Aurelius is the most accessible, but Seneca is better for those who want more of a narrative and exposition. Epictetus is probably the hardest one to start with. One of the reasons we created The Daily Stoic was to give people a place to get a sampling of all the big three and then some of the others like Zeno and Cleanthes. You can also go to for a daily email of Stoic thinking and interviews. I’m a big fan of r/Stoicism on Reddit as well and post there pretty often because the discussions are great.

But the best way to start is the same way people have been starting with centuries: with one the text of one of the masters. Read it and think about it and read it again!

Obstacle is the WayQ: Do you have anything else that you wanted to mention while we have the chance?

Not really—I hope people like what I have to say. Not everyone understands or appreciates what I’ve tried to do with Stoicism but I do hope they can see that I am genuine in my interest (I don’t want to say passion) for Stoicism and I’ll talk about it with anyone, anywhere. I always try to explain that the vast majority of people are turned off to philosophy because of how its historically been taught, but if you sell them on what philosophy can do for them they are much more open to it. That’s what my writing is about and I’m going to bring Stoicism to as many people as I can that way!

Ryan Holiday is the author of three books on Stoicism: The Obstacle is the Way, Ego is the Enemy, and his latest The Daily Stoic.

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