The Obstacle Is the Way

This book by Ryan Holiday has been genuinely recommended 3 times on Tim Ferriss. The people who vouched for it on air: Christopher Sommer, Rana el Kaliouby, Tim Ferriss. It comes up in conversations about depression & mood, exercise & strength, longevity & aging, meditation & mindfulness. The earliest recommendation we indexed is from Apr 2020 and the most recent from Apr 2025. Every quote below is verbatim, attributed, and linked to the exact second it was said. Sourced expert opinion, not medical advice.

1 Wall Street Journal Bestseller The Obstacle is the Way has become a cult classic, beloved by men and women around the world who apply its wisdom to become more successful at whatever they do. Its many fans include a former governor and movie star (Arnold Schwarzenegger), a hip hop icon (LL Cool J), an Irish tennis pro (James McGee), an NBC sportscaster (Michele Tafoya), and the coaches and players of winning teams like the New England Patriots, Seattle Seahawks, Chicago Cubs, and University of Texas men’s basketball team.

• “An example of that for stoicism would be certainly Ryan Holiday's work. He's right here nearby. Obstacle is the way and so on.”

  Why it counts as a recommendation: “an example of that for stoicism would be certainly Ryan Holiday's work”
  Tim Ferriss · The Tim Ferriss Show · Apr 202501:17:27

  Said during "From Stocking Groceries to Reading Philosophy for a Living, Stephen West of Philosophize This!". The episode features Stephen West: Creator and host of the Philosophize This! podcast, a self-taught philosopher who went from a high-school dropout stocking groceries to running one of the most respected independent philosophy shows; 225 episodes in over 12 years, with a book deal coming in 2026. Philosophize This! creator Stephen West tells Tim Ferriss how a homeless dropout warehouse worker built a beloved philosophy podcast.

• “What I'm enjoying right now and I'm just getting into it is the obstacle is the way oh yeah by Ryan holiday very close friend of mine”

  Why it counts as a recommendation: “What I'm enjoying right now ... is the obstacle is the way ... that's a great book”
  Christopher Sommer · The Tim Ferriss Show · Jun 202402:59:09

  Said during "Pavel Tsatsouline and Chris Sommer, The Tim Ferriss Show". The episode features Pavel Tsatsouline and Christopher Sommer: Pavel Tsatsouline is the founder and CEO of StrongFirst, the strength coach who brought the Russian kettlebell to the West; Christopher Sommer is a former US national team gymnastics coach and founder of the Gymnastic Bodies training system. Two strength legends, Pavel Tsatsouline and Christopher Sommer, explain why strength is a skill and patience builds bodies that last.

• “I've recently been gifting I must have given this book to at least like three or four people cuz I recently read it. Uh The Obstacle Is the Way.”

  Why it counts as a recommendation: “I must have given this book to at least like three or four people”
  Rana el Kaliouby · The Tim Ferriss Show · Apr 202000:57:18

  Said during "Rana el Kaliouby, AI, Emotional Intelligence, and The Journey of Finding Oneself". The episode features Rana el Kaliouby: Egyptian-American computer scientist and pioneer of 'emotion AI,' co-founder and CEO of Affectiva. She holds a PhD from Cambridge, did a postdoc at MIT, and wrote the memoir Girl Decoded. Emotion AI pioneer Rana el Kaliouby on teaching machines emotional intelligence, her journey from Cairo to CEO, and embracing her own emotions.