Ryan Holiday Books & Key Ideas

Ryan Holiday is an American author and former director of marketing at American Apparel, best known for writing about Stoic philosophy. He has written a series of bestselling books applying Stoic philosophy to modern life, including The Obstacle Is the Way and Ego Is the Enemy.

Who is Ryan Holiday?

Ryan Holiday dropped out of college at 19 and went on to work in marketing before becoming a full-time writer. He discovered Stoicism while working with the author Robert Greene, and has since written more than ten books on discipline, ego, stillness and turning obstacles into advantages. He also runs a daily email that reaches hundreds of thousands of readers.

Ryan Holiday’s books

Where should you start?

Start with The Obstacle Is the Way. It is the most practical introduction to his version of Stoicism and the book that made his name.

Key ideas in Ryan Holiday’s work

  • The obstacle is the way — the thing standing in your way is often the path forward
  • Ego is the enemy — the less attached you are to being right, the more you can actually accomplish
  • Stillness — quieting the mind is a prerequisite for good decisions
  • Focus on what you control — the core Stoic discipline applied to the modern world

Frequently asked questions

What is Ryan Holiday best known for?
Ryan Holiday is best known for applying Stoic philosophy to modern life and work, in books like The Obstacle Is the Way and Ego Is the Enemy.

Should I read The Obstacle Is the Way first?
Yes. It is the clearest introduction to his thinking, and his later books assume you already know it.