Ryan Holiday dropped out of college, read Seneca, and built a life around Stoicism before it was cool. This conversation covers how to say no to money, why writing well starts with a pen and a shoebox, and why your success might be the thing that ruins you—if you let it.
Listen on: Apple Podcasts | Spotify | Transcript
Ryan is the author of several books, including Trust Me I’m Lying, The Obstacle is the Way, and Ego is the Enemy.
Here are a few highlights from our conversation:
- What Stoicism is and how it differs from many of the mainstream “philosophies” you learn about in school
- How Dr. Drew is partially responsible for putting Ryan on the Stoic path
- How Stoicism has helped Ryan navigate some of the challenges he’s faced in his life
- How Ryan juggles everything he has to do as a writer, a business owner, and consultant
- The impact working with Robert Greene had on Ryan and how that experience influenced everything from his writing, how he does research, and even the kind of person he turned out to be
- How Ryan uses the famous Notecard System he learned as a researcher for Robert Greene
- Why Ryan insists on writing his thoughts longhand, and why copy and paste is almost a capital offense
- The process Ryan uses to write a book and what the ideation, writing and editing stages look like
- The brilliant way Ryan runs his consulting business, including how he charges clients and how he gracefully handles people looking for free advice
You’re going to get so much out of this episode. Enjoy!
Books Mentioned
- Marcus Aurelius Meditations
- Diogenes Laertius Lives of Eminent Philosophers (Stoics in Book 7)
- Robert Greene, The 48 Laws of Power
- James Romm Dying Every Day: Seneca at the Court of Nero
- Pierre Hadot The Inner Citadel
- Robert Caro, The Years of Lyndon Johnson
