Ryan Holiday’s Stoic Advice to Writers With Something to Say

Editor’s Note: I’m pleased to feature this interview with author and marketing pro Ryan Holiday as part of the Winning Edits Expert Interview Series.

Ryan is a media strategist, adviser to bestselling authors, writer, and Director of Marketing at American Apparel.

Many of his in-depth, thought-provoking articles have been published on Tim Ferriss’s blog.

He writes for his own site, www.RyanHoliday.net, where he tries to talk about the things that he wishes blogs would talk about more often: life, dealing with assholes, how to be self-critical and self-aware, humility, philosophy, reading and strategy.

Matt Gartland: Your Stoicism 101: A Practical Guide for Entrepreneurs article (published on Tim Ferriss’s blog) was my first interaction with you and your writing. Consequently, it was also my first interaction with formal Stoic teachings. I was an instant fan.

You wrote in the article that Stoicism is “preparation for the philosophic life – an action – where the right state of mind is the most critical part.” At the end, you share some of your favorite Stoic reminders. How have you adapted those reminders not just to living life but analyzing and writing about life in deeply considered ways?

Ryan Holiday: If you notice the breadth of topics I discuss on my blog is not large. I’m normally turning over the same handful of themes in different ways with different words. This is something I took from the Stoics. You could argue that there isn’t an original word in Marcus Aurelius’s Meditations. Almost everything in it can be traced back to some earlier philosopher and when he isn’t directly quoting, he is summarizing and paraphrasing.

He was participating in a spiritual exercise when he wrote those notes to himself. He was trying to properly orient himself, correct bad emotions or impulses and stay in the right frame of mind. I try to do that with my site. The only difference is I do it more publicly. I’m not sure why, but I do. It’s helped me meet a lot of interesting people. A this public discussion forces me to be clearer and holds me accountable.

An analogy: when I was writing my book, a really smart, successful author I know recommended that I read the entire manuscript out loud either to someone else or record it. This way I could allow my mind to skip over inconsistent parts or get away with darlings or say things I’d never say in real life. I see my blog in the same light now. I’m saying the stuff out loud instead of just repeating things in my head.

MG: You expose the false genius of most ideas in a recent article. Rather than two second epiphanies, you write that great contributions “come from taking the time to develop a deep understanding of everything at play and more often than not, coming up with gradual improvements and suggestions.”

As a lover and student of books, how do great authors apply this premise to their work? And, given modern publishing trends, do you sense that the ethics of what a “book” is are decaying?

RH: In that instance, I was talking a bit more directly about blogging or about office politics. Where people think the first thing that pops into your head is genius and have no humility or patience to think about why things are the way they are and what factors might be at play.

I guess there is probably a connection to that mindset and ebooks or Kindle singles or whatever. Jon Stuart Mill talks about this a little in his autobiography. He says something like books are great because they don’t necessarily need to be successful right away. Normally the author isn’t entirely dependent on them for money and the market is a bit more insulated from immediate pressures. And that is a good thing that encourages the right ideas.

Blogging or journalism is different; you not only have to turn it around quickly but it’s got to make a splash the day it is published. Nobody reads old newspaper pieces from 30 years ago but there are still plenty of books with daily relevance that are that old — and obviously much older.

The process of sitting down and really thinking about a big idea for a year or even several years as you write it all down produces a final product that stands the test of time. If done right it is thoughtful, comprehensive, and reasonable. I rarely read anything online that meets any of those criteria, let alone all of them.

MG: You once wrote that “stories are worthless because they’re mental creations – they are not reality.”

I agree with your arguments that stories that “trick” us into false perceptions of ourselves are dubious and wicked. But I also believe that stories, used well, are necessary instruments for communication, identification, education and entertainment.

Do you agree that these two viewpoints are not mutually exclusive? And can excellence in storytelling be both humble and epic?

RH: Of course. I use stories all the time in my writing or in my work. It’s unquestionably the best way to convince people of things or to explain ideas. I don’t think I could read as much as I do if I didn’t enjoy or cherish the art of the story.

But there is a big difference between those stories and the stories we tell ourselves about ourselves. When you call yourself an entrepreneur, you’re telling yourself a story. When you call yourself an artist, you’re telling yourself a story. I prefer to let other people do the telling while I do the work. I leave events unconnected as best I can and focus on the present — which is devoid of narrative, past or future.

MG: You seemingly read books by the boatload. You recommended over 150 books in 2011, which hints at some ridiculous number actually read. These aren’t fluff books. And you don’t read for contact highs.

In Read to Lead: How to Digest Books Above Your “Level”, you write that “Reading to lead or learn requires that you treat your brain like the muscle that it is – lifting the subjects with the most tension and weight. For me, that means pushing ahead into subjects you’re not familiar with and wresting with them until you can…”

What big subjects are you exploring now? And how should readers interested in yet overwhelmed by such deep reading begin their shift in reading style?

While I was writing my book it was really hard to focus on that and explore new subjects. So I ended up reading a lot of fiction and biographies, since they are both self-contained. But even when I do those things, I tend to follow themes.

Most of the fiction and memoirs I’ve read in the last few months have been focused around Los Angeles. So I read everything Raymond Chandler ever wrote and most of the books about him too. Then I read Carey McWilliams's book about Los Angeles as well as his autobiography. And then everything by his friend John Fante and the works about him too.

I lived in LA for 5 years and I just could not understand the city, especially in light of other cities I loved like New York or New Orleans (where I live now). But after I randomly picked up one of these books, it gave me a glimmer of understanding–a hint into its past as a real place with history and people and life–and I chased it until I felt like I had a totally new grasp on it.

Anyway, the key to deep reading is to be fascinated by the subject and to not let anything stand in your way. Go to the book store and buy every book you want, don’t worry about the price. Or decide to stay in one night and just dedicate yourself to getting to the bottom of it. Ask questions, talk to people about it. Tell them what you’re learning. Read every article, Wikipedia page or link you can find. To me this is all a lot of fun and that’s why I do it.

MG: What’s the #1 piece of actionable advice you’d give to writers trying to write a compelling book that attracts the attention and admiration of critical-thinking readers such as yourself?

RH: Have something to say. Something you really really MUST say. Anything less than that is a book done for the wrong reasons.

I’d say half the books I pick up (and throw down) fall into that category. Especially books by academics or the literature set–they don’t have anything to say, they just want to talk. And they want you to know how smart they are. That all being said, my attention or admiration is not what matters. There’s a lot of great books out there that are just not for me. What matters is whoever your particular audience is (sometimes, they’re people just like you) and that is who you should write for.

More about Ryan:

Ryan Holiday is 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. He currently lives in New Orleans, where he is writing a book, and this is his rebellious puppy, Hanno.

Images provided by and used with permission from the interviewee.