Uncommon Wisdom on Reading, Writing, and Publishing from Ryan Holiday

picture-238129Ryan Holiday, director of marketing at American Apparel, is still in his twenties and has already published three books, including the best-seller Trust Me I’m Lying: Confessions of a Media Manipulator. Though steeped in the craft of advertising and at home on the Web, he reads like a maniac and writes thousands of words per week.

“The walls of my house are covered in books from floor to ceiling,” he confessed in a recent post. “The last time I moved, I had to rent a U-Haul exclusively for books. At first that frustrated me, and then I remembered that books paid the rent on both those houses. They kept me sane, they made me a lot of money.”

I find a lot of practical wisdom in Ryan’s views on reading, writing, and publishing. So I want to highlight some of his posts and link you to the original sources.

So You Want To Be A Writer? That’s Mistake #1

Ryan begins by quoting Schopenhauer, who distinguished between people “who write because they have something they have to say and those who write for the sake of writing.” Too much writing advice is directed toward the latter.

“The problem is identifying as a writer,” Ryan notes. “As though assembling words together is somehow its own activity. It isn’t. It’s a means to an end. And that end is always to say something, to speak some truth or reach someone outside yourself.”

So You Want To Write A Book? “Want” Is Not Nearly Enough

Writing a book is not therapy. It’s not an “interesting” experience or hobby. It’s work that takes over your life for too long and chews you up until you finish.

“If you honestly think you might be fine if you nixed the [book] project and went on with your life as though the idea never occurred to you–then For The Love Of God, save yourself the anguish and do that,” Ryan advises. “If, on the other hand, this idea keeps you up at night, it dominates your conversations and reading habits, if it feels like you’ll explode if you don’t get it all down, if your back is to the wall–then congratulations, it sounds like you’ve got a book in you.”

If you belong to the latter group, then remembering three things can help a lot:

  • Much of the work—researching and outlining—is done before you write a first draft.
  • Begin by stating the essence of your book in one sentence, one paragraph, and one page.
  • When you get “writer’s block,” talk through your ideas with someone who listens well.

How To Write A Great Essay About Anything

Ryan defines essays as “written compositions about anything.” Articles, blog posts, college papers, reports, memos, and longish emails are all included.

To begin, he writes, remember that “you need only to create a handful of original sentences for the entire essay: a thesis, a theme, a mini-thesis that begins each paragraph and a concluding sentence that says what it all means. Everything else is a variation of these four sentences in some way.” For more details, see the post.

How To Read More — A Lot More

“Reading must become as natural as eating and breathing to you,” Ryan observes. It’s not something you do because you feel like it, but because it’s a reflex, a default.”

“Perhaps the reason you’re having trouble is you forgot the purpose of reading,” he adds. “It’s not just for fun. Human beings have been recording their knowledge in book form for more than 5,000 years. That means that whatever you’re working on right now, whatever problem you’re struggling with, is probably addressed in some book somewhere by someone a lot smarter than you.”

Read To Lead: How To Digest Books Above Your “Level

“I may have been a college drop out,” Ryan notes, “but I have had the best teachers in the world: tough books.” To get the most from them:

  • Ruin the ending by previewing the book to discover its basic assertions up front.
  • Focus like a laser on answering two questions about the book: “1) What does it mean? 2) Do you agree with it?”
  • Look up unfamiliar words right away.
  • Mark every passage that interests you and write notes to yourself in the margins.
  • Wait a week or two after finishing the book and then add the marked passages and marginalia to your commonplace book. (More about this below.)
  • Bring the ideas you marked to life by using them in conversation, acting on them, and quoting them in your own writing.
  • Choose your next book from those listed in the footnotes or bibliography of the book you just finished.

Information Vs. Knowledge Vs. Experience

Today were are blessed by easy access to thousands of blogs, books, videos, and free online courses. John Butman calls it the ideaplex.

“But there is a dark side to this glut of free information,” Ryan notes. “It’s enabled a whole industry of self-help gurus, life coaches, and social media marketers to sell snake oil to the masses, tricking people–people who genuinely want to improve their lives–into thinking they can get something for nothing.”

Ryan reminds us that knowledge requires experience, “the back and forth feedback loop–between theory and practice, hypothesis and results, ideas and action.”

How And Why To Keep A “Commonplace Book”

“A commonplace book is a central resource or depository for ideas, quotes, anecdotes, observations and information you come across during your life and didactic pursuits,” Ryan notes. “The purpose of the book is to record and organize these gems for later use in your life, in your business, in your writing, speaking or whatever it is that you do.”

Commonplace books have a long history. Montaigne used one. So did Marcus Aurelius, Petrarch, Napoleon, Thomas Jefferson, H. L. Mencken, and Ronald Reagan. Bill Gates does, and Ryan suggests that you do, too. This is especially wise if you are an idea entrepreneur—someone who makes a living by writing, speaking, training, and consulting.

Ryan is unusual in that his commonplace book is totally analog—thousands of handwritten index cards filed by category. However, you can use digital tools as well. I offer suggestions here.

For more of Ryan’s ideas on commonplace books, see:

The Right (And Wrong) Way To Market A Book

If you really want your book to get attention, then remember that marketing it does not come after writing. Rather, start marketing the book three years before it’s published.

Also remember that the best marketing decision you can make is to write an indispensable book. “By doing that you create the only marketing that matters,” Ryan notes: “word of mouth.”

This post offers plenty of gritty marketing advice. Supplement it with The Overthinker’s Guide To Launching Your Next Project Without Wanting To Kill Yourself

How I Wrote Three Books in Three Years

The first two suggestions alone—”always be researching” and “know where you’re going (have a plan)”—can save you hours of heartbreak.

If You Want More

Check out Ryan’s posts on Thought Catalog. Also see my Readlist of personal favorites.


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