Ryan Holiday on how to conceive, research, and write a “Big Idea” book

“Most people do not wake up and think, ‘I need more philosophy in my life.’ They do wake up and think ‘I have a problem and I need a solution’.” –Ryan Holiday

Ryan Holiday (@RyanHoliday) is an American marketer and entrepreneur, and the author of eight books, including The Obstacle is the Way, Ego is the Enemy, and Stillness is the Key, which debuts in bookstores this week.

In this episode of Deviate, Ryan and Rolf talk about “Big Idea” books, how Ryan’s philosophical trilogy of books came about, and how word-of-mouth works better than categorization in helping people find your books (3:00); how storytelling is better than dry analysis when it comes to writing books on a topic like Stoicism, and how writing for general audiences differs from writing for “elite” audiences (16:00); why ancient ideas and examples are often more dependable than contemporary ones, and why it’s good to read as diversely as possible (25:00); what a “commonplace book” is, and how it can fuel your creative life (32:30); the difference in focus between the research phase of a book and the writing phase, and how to best plan and structure books (48:00); Ryan’s writing habits, how he balances his day with non-writing tasks, and the importance of maintaining momentum (1:01:30); and the process of how he decides on which themes and projects to explore next (1:06:00).

Books mentioned:

• The 4-Hour Work Week, by Tim Ferriss
• Vagabonding, by Rolf Potts
• The 48 Laws of Power, by Robert Greene
• The History of the Peloponnesian War, by Thucydides
• Cash: The Autobiography, by Johnny Cash
• The War of Art, by Steven Pressfield
• Range, by David Epstein
• The Daily Stoic, by Ryan Holiday
• The Hero With a Thousand Faces, by Joseph Campbell

Notable links:

• Big Idea Book Bootcamp (writing class)
• Tim Ferriss book club
• How a book on stoicism became wildly popular at every level of the NFL (article)
• How And Why To Keep A “Commonplace Book” (article)
• Ronald Reagan Presidential Library and Museum
• Marina Abramovich “The Artist is Present”
• A Beautiful Day in the Neighborhood (Mister Rogers movie)
• Stanford Prison Experiment (psychology experiment)
• Dorothy Day (American Catholic social activist)

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The Deviate theme music comes from the title track of Cedar Van Tassel’s 2017 album Lumber.

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