About Ryan Holiday
Ryan Holiday dropped out of college at 19 to apprentice under author Robert Greene. He spent years as a media strategist for American Apparel and other clients before pivoting to writing full-time. The Obstacle Is the Way (2014) — drawing on Marcus Aurelius, Seneca, and Epictetus — became a word-of-mouth sensation when NFL coaches started assigning it to players.
Holiday has become the most influential popularizer of Stoic philosophy in the English-speaking world. He runs the Daily Stoic newsletter, operates a bookstore in Austin, Texas, and has produced dozens of books, courses, and podcast episodes on ancient philosophy. His writing is direct, punchy, and heavily focused on practical application over academic nuance.
The Stoic Trilogy
The Virtue Books
Other Notable Books
Reading Guide
Where to start
Start with The Obstacle Is the Way — it's his best and most focused book. Short enough to read in a weekend, dense enough to revisit repeatedly.
Then read the rest of the Stoic Trilogy in order: Ego Is the Enemy → Stillness Is the Key. They're thematically linked but each stands alone.
For daily practice, The Daily Stoic is the best companion — one page per morning. For going deeper into the original philosophy, try Marcus Aurelius's Meditations directly alongside Holiday's work.