Ryan Holiday is not just a writer, he’s one of my absolute favourite writers. Ryan dropped out of college at 19 years old to apprentice under Robert Green, the author of The 48 Laws of Power. Working his way up in the world of media, he became the director of marketing for American Apparel. Whilst he is known for his incredible non-fiction books, Ryan Holiday also heads up his creative agency Brass Check, who have advised clients like Google, TASER, and Complex, as well as many prominent bestselling authors, including Neil Strauss, Tony Robbins and Tim Ferriss. Ryan Holiday is the author of numerous books, with perhaps his most popular (and my personal favourite) being The Obstacle Is the Way; a book that has been translated into more than twenty languages. His new book, Perennial Seller: The Art of Making and Marketing Work that Lasts, is a meditation on the ingredients required to create classic books, businesses, and art that does more than just disappear. I’m excited to pick up my copy, given the abundance of positive reviews the book has already received. Ryan Holiday has also written for many popular publications, including; New York Observer, Entrepreneur, Fast Company, The Huffington Post, Medium, Forbes and multiple other outlets. Another drive for me to interview Ryan Holiday is that he is a prolific reader. Anyone who subscribes to his monthly email that documents what he’s been reading each month knows that Ryan will typically read around 250 books every year! I was extremely excited to have the chance to talk books with one of my favourite writers; I know you’re going to find value in this conversation. Please enjoy my interview with the wildly talented, Ryan Holiday…
When someone asks you ‘what do you do for a living?’ – How do you respond?
I am an author and also consult writers, musicians and startups through Brass Check, my creative advisory firm.
I just finished the post-presidency memoir At Ease: Stories I Only Tell My Friends by Dwight Eisenhower. I started The Master and Margarita by Mikhail Bulgakov last night.
What’s your earliest memory of reading?
I remember I had a grandmother who was a reading teacher at an elementary school and I remember actually not liking going over to her house because she would always made me read. It seemed like a chore. Things change, I guess. I remember in high school I hated running but my parents wanted me to run cross country and track. It was a chore. But now I do it on purpose nearly every day. Life is strange like that.
If you could encourage young people to read one book in particular, what would it be?
Meditations by Marcus Aurelius. It is the private thoughts of the world’s most powerful man giving advice to himself on how to make good on the responsibilities and obligations of his positions. Trained in Stoic philosophy, Marcus stopped almost every night to practice a series of spiritual exercises—reminders designed to make him humble, patient, empathetic, generous, and strong in the face of whatever he was dealing with. Well, now we have this book. It is imminently readable and perfectly accessible. You cannot read this book and not come away with a phrase or a line that will be helpful to you next time you are in trouble.
Can you remember the first you wrote something you were proud of?
I’m sure there many things that ended up on the fridge at home as a kid but I don’t know what that’s worth. I wrote an essay about The Great Gatsby my sophomore or junior year of high school that I remember coming into class one day to find that the english teacher had printed out and was teaching to the class (I actually broke the essay down in an article a while ago). She was the first teacher, person really, that saw something in me as a writer and pushed me to pursue it. I still have the letter of recommendation she wrote for me for college.
What is the worst job you’ve ever had?
I made sandwiches and stocked shelves in a deli. I was a grill cook at Wendy’s. I was a lifeguard. I worked in a BBQ restaurant. I filled out online surveys to make money in college. I’ve done a lot.
What two pieces of advice would you give a young aspiring writer?
Go.Do.Interesting.Things. Read a lot. That’s all there is.
Do you read as much as you’d like to?
I’ve slowed down the last year or so. The amount of writing I’ve done has picked up tremendously so I feel like I have this backlog of things to say and less to read about. I’ve also found myself getting disappointed with a lot of stuff I read. Bad writing, poor thinking, annoying decisions. It’s hard for me to focus when I see that, especially at home. But I suck down books when I travel so I get plenty in.
When and how did you discover Stoicism?
I was in college I was invited to this little summit of college journalists that Dr. Drew, then the host of Loveline, was hosting. After it ended, he was standing in the corner and I cautiously made my way over to nervously ask a question. I knew he was a big reader and I’d heard someone ask it on Loveline before. I said, “I heard you read a lot. What should I read?” He said he’d been studying a Stoic philosopher named Epictetus and that I should check it out. I rushed back to my room and bought it. My life has not been the same since.
Which path is that? I’m on a few. As a writer, The War of Art by Steven Pressfield. Cyril Connolly. Bird by Bird by Anne Lamott. Cheryl Strayed. Austin Kleon. Mastery by Robert Greene. Business? Blue Ocean Strategy by W. Chan Kim and Renee Mauborgne. Purple Cow by Seth Godin. Paul Graham’s essays. Zero to One by Peter Thiel. As a person? The Stoics. As a rancher? Hard Scrabble by John Graves.
Is there a book that you’ve read more than once? What is it and why did you revisit it?
I’ve read Meditations by Marcus Aurelius easily a hundred times in the last 10 or so years. I keep one on my desk and flip through it whenever I have a second.
What book have you recommended the most to friends and family?
Honestly, I don’t really recommend books to friends or family. People think I must be constantly running around doing that because of my reading list email and my job, but really I don’t. Partly because they hear me give the recommendations there or we talk about other things. I don’t think my wife has read a book I’ve read in like ten years.
Who would you say are the three writers that continue to inspire you?
Rich Cohen. Steven Pressfield. Robert Greene.
What’s your favourite genre of book?
Fucking good books man. Who cares what genre they’re in? I like old books. I like fiction. I like new business books. I like poetry. I like the classics. But only the ones that: teach you something about life. That deserve the pages they are printed on.
What do you think a world without books would be like?
It’d have a lot more painful trial and error, that’s for sure.
Is there an author whose writing you’re such a fan of, that you’ll read everything they release?
Michael Lewis is one of the only people on the planet whose books I preorder.
Do you think digital books will ever completely replace real books?
In Sci-fi movies the buildings always have these futuristic doors that open automatically or get sucked into the ceilings. We could probably have that right now but the technology of a piece of wood or steel on a hinge is hard to beat. Same goes for books.
What book do you feel humanity needs most right now?
I sort of answered this question already with Meditations so if I tweak your meaning slightly I would say there was a passage in Enemies of Promise by Cyril Connolly was very influential in the direction of my career and also my newest book, Perennial Seller, and shaping its vision at the very beginning. I will quote it in full:
“THE NEXT TEN YEARS
(1) What will have happened to the world in ten years’ time?
(2) To me? To my friends?
(3) To the books they write?
Above all to the books—for, to put it another way, I have one ambition—to write a book that will hold good for ten years afterwards. And of how many is that true to-day? I make it ten years because for ten years I have written about books, and because I can say, and this is the gravest warning, that in a short time the writing of books, especially works of the imagination which last that long, will be an extinct art. Contemporary books do not keep. The quality in them which makes for their success is the first to go; they turn over night. Therefore one must look for some quality which improves with time. The short-lived success of a book may be the fault of the reader for newspapers, libraries, book-societies, broadcasting and the cinema have vitiated the art of reading. But the books of which I am thinking have all been read once, and have all seemed good to discriminating readers. They go bad just the same.”
The point is that books should last and if they aren’t lasting, why are you writing them? Or reading them?
Are there any books you haven’t mentioned that you feel would make your reading list?
I’m staring at my shelves right now and clearly have left a lot out. I can’t rave enough about Budd Schulberg or Walker Percy or John Fante (my three favorite novelists). I think Plutarch is probably the best to ever play the biography game. I like Klosterman a lot.
What books or subject matter do you plan on reading in the next year?
I only take it one book at a time. I let the intuition guide me there, I don’t make plans.
If you were to write an autobiography – what would it be called?
My memory isn’t good enough for an autobiography, nor my life that interesting, so I have no plans for one.