Ryan Holiday Author Interview

Portrait of Ryan Holiday

Ryan Holiday is the bestselling author of Trust Me, I’m Lying; Conspiracy; and many other books about marketing, culture, and the human condition. His work has been translated into thirty languages and has appeared everywhere from the New York Times to Fast Company. His company, Brass Check, has advised companies such as Google, TASER, and Complex, as well as multiplatinum musicians and some of the biggest authors in the world.

He’s written three books that explore ancient wisdom for contemporary readers: The Obstacle Is the Way; Ego Is the Enemy; and his new book Stillness Is the Key. This latest book has generated a tremendous amount of buzz: it was a #1 New York Times bestseller as well as a Wall Street Journal bestseller.

Drawing on a wide range of history’s greatest thinkers, from Confucius to Seneca, Marcus Aurelius to Thich Nhat Hanh, John Stuart Mill to Nietzsche, Ryan Holiday argues that stillness is not mere inactivity, but the doorway to self-mastery, discipline, and focus.

As someone who loves great quotations, I also want to mention his earlier book The Daily Stoic: 366 Meditations on Wisdom, Perseverance, and the Art of Living. I love this kind of book.

I couldn’t wait to talk to Ryan about happiness, habits, and productivity.

Gretchen: What’s a simple activity or habit that consistently makes you happier, healthier, more productive, or more creative? 

Ryan: An easy one: I don’t use my phone for the first hour I am awake. To me, the worst thing you can do is start the day on your back foot, reacting to whatever came in last night or whatever somebody said on social media. I want the morning to be peaceful and serene and present. So that means not using the phone as an alarm clock, no sleeping with it in your room, and it means ignoring it in the morning. I’d rather go for a walk (and not take pictures!) with my kids, or a run, or read a book over breakfast or get right into my writing. I can catch up with my texts and emails later.

What’s something you know now about happiness that you didn’t know when you were 18 years old?

An interesting study I read a few years ago said that younger people associate happiness with achievement and older people with contentment. It’s something that certainly tracks with my experience. I thought I needed to do or have a bunch of things to be happy—and so that figured into a lot of my drive and work. It was positive in some sense, but also really draining in others. Today, I’m much more able to understand that happiness usually comes from a place of stillness, from feeling like you have enough in the moment, whatever that is. Even if it’s sitting in traffic or working really hard, you have to figure out how to enjoy what’s in front of you rather than see it as a means to an end.

Of everything you’ve learned, what has surprised or intrigued you—or your readers—most? 

At the core of my writing is really this idea that there’s nothing new under the sun and that wise people a really long time ago—in my case, mostly the Stoics—figured out most of the things we need to know. So my study and my writing is about surfacing those ideas and translating them in a context. Epictetus said: “It’s not things that upset us, it’s our judgment about things.” I love that. I love stuff like that, and I love that it came from a Greek slave 2,000 years ago. It’s so wonderful finding out that these insights are repeatedly confirmed by science and psychology and of course, personal experience.

Have you ever managed to gain a challenging healthy habit—or to break an unhealthy habit? If so, how did you do it?

There wouldn’t be much point to what we do if we hadn’t, would there? I’m always depressed when I talk to people who believe we are fixed, can’t change, can’t grow or build new habits. Of course we can! I’m always quitting things. I quit soda seven or eight years ago. My wife hated that I chewed gum, so I quit that earlier this year. I quit Facebook in January, which has been wonderful for my mental health in a lot of ways. I don’t have social media on my phone. My wife has been pushing me to start using sunscreen, which has turned out to be a hard habit to start after so many years of just never thinking about it. But I’m building a routine in the evening and the morning about it that has made it more possible. Even the no-phone mornings one is relatively new—but I did it using an app called Spar that charges you money and puts you in an accountability group. I used the app to build a daily pushup habit too. They do it through what they call “challenges,” so I love that word.

Point being: Of course you can add new habits and break bad ones. You start small and you build.

Would you describe yourself as an Upholder, a Questioner, a Rebel, or an Obliger?

I’m a Rebel but I have strong Upholder tendencies too. I like both sides of that, and think they work well in balance. You want to do what’s expected, but not blindly. You want to think for yourself but also not do things out of spite.

Does anything tend to interfere with your ability to keep your healthy habits or your happiness? (e.g. travel, parties, email)

Travel is always disruptive. Having kids also threw some of my routines and habits in disorder—suddenly the house is filled with foods I shouldn’t be eating! There’s always an excuse! What I’ve tried to get better at is being less rigid but more resilient. So instead of thinking about my “routine,” I practice routines. I want to have multiple ones, which gives me flexibility and adaptability if I am on the road. Or if the morning gets disrupted. Or if something comes up. I think about my habits—going for a walk, exercise, journaling, etc—more as touchstones. Or like cards in a deck. It doesn’t matter what order they go in. I’m cool if they get shuffled. But I am always going to come back to them.

Have you ever been hit by a lightning bolt, where you made a major change very suddenly, as a consequence of reading a book, a conversation with a friend, a milestone birthday, a health scare, etc.?

I’m not a huge believer in epiphanies. I love process. Sure there are moments where things have hit me, but when I think of the real impact, it’s come not from that moment, but from mulling that moment over. It’s not from one book, one time, but from reading and re-reading, from discussing and writing about it. The Buddhists talk about “satori” when you get hit with enlightenment, and maybe that just hasn’t happened for me yet, but I’ve felt like wisdom is more accretive, than sudden. I think thinking about it that way is more attainable anyway. To wait or to look for a breakthrough is probably to set yourself up for disappointment. To see it as a job you show up to every day and work at, at least in my opinion, is more likely to produce results.

Is there a particular motto or saying that you’ve found very helpful? (e.g., I remind myself to “Be Gretchen.”)

Memento Mori is the big one for me. I carry a coin in my pocket with that on it. Because it’s true. We are mortal. We are going to die. Each of us—today or a hundred years from now. We gain nothing by denying it. But by embracing it, we have urgency, we have clarity, we have truth. “You can leave life right now,” Marcus Aurelius said, “Let that determine what you do and say and think.” I carry that motto on my physically so I can try to live by it.

Has a book ever changed your life—if so, which one and why? 

Marcus Aurelius’s Meditations was the big one. I read it at 19 or 20 and it changed the course of my life as a person, as a writer, as a thinker. How could it not? The most powerful person in the world, writing private notes to himself about how to be better, how to follow the philosophy that shaped him? It’s just fantastic. So special and unique. I urge everyone to read it. And then to read it again and again. It changes and you change as you go—which is actually an idea in the book. “No man steps in the same river twice,” he quotes Heraclitus as saying. Because the river changes and so do we.

In your field, is there a common misperception or incorrect assumption that you’d like to correct?

I mentioned philosophy a couple times. Philosophy is not what philosophy departments think it is. It’s not turtlenecked university professors. It’s real advice for the real world from real people—at least the philosophy that matters. That’s what I try to popularize in my books and with DailyStoic.com. We all have problems. We all have potential we’re not realizing. We all deserve to flourish and to live what the ancients called “the good life.” Philosophy is the way there. But engaging with it as a process and a pursuit. Study it everyday. Put its advice in to practice. Review. Repeat. That’s the journey I am on and I think that you’re on, and that I think we both agree we’d love to have more people join us on!



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