Josh Waitzkin and Tim Ferriss on The Cave Process, Advice from Future Selves, and Training for an Uncertain Future (#498)

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Most of the great performers that I’ve known or competed against or worked with in different fields just had this beautiful connection between their areas of dysfunctionality and brilliance. Sometimes the very thing that helps them excel in their professional life, or their artistic life, or their competitive life, is something that in their personal life can be a little bit awkward.

— Josh Waitzkin

Josh Waitzkin, author of The Art of Learning: An Inner Journey to Optimal Performance, is an eight-time national chess champion, a two-time world champion in Tai Chi Chuan Push Hands, and the first Brazilian Jiu-Jitsu black belt under nine-time world champion Marcelo Garcia.

For the past 13 years, Josh has been channeling his passion for the outer limits of the learning process toward training elite mental performers in business and finance and to revolutionizing the education system through his nonprofit foundation, The Art of Learning Project. Josh is currently in the process of taking on his fourth and fifth disciplines, paddle surfing and foiling, and is an all-in father and husband.

Please enjoy!

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#498: Josh Waitzkin and Tim Ferriss on The Cave Process, Advice from Future Selves, and Training for an Uncertain Future


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What was your favorite quote or lesson from this episode? Please let me know in the comments.


Want to hear another episode with Josh Waitzkin? Listen to our last conversation, in which we discussed changing assumptions and shared constructs, the benefits of being a beginner, practicing the art of falling, writing exercises, feedback loops, the unexpected rewards of approaching skill acquisition in an unorthodox way, and much more!

#412: Josh Waitzkin on Beginner’s Mind, Self-Actualization, and Advice from Your Future Self



  • Connect with Josh Waitzkin:

Website | The Art of Learning Project


  • What are gating questions, what are they intended to fish out, and how do I go about constructing them? [08:48]
  • What patterns might emerge if we were to gauge the insights others gain from being asked these gating questions? [16:40]
  • Pondering the entanglement of genius and eccentricity, and how it shows up in Usain Bolt’s unusual stride and Marcelo Gracie’s ability to learn from making a mistake just once. [20:11]
  • How do I view this entanglement (or dysfunction) in my own life, and how does it manifest in ways the public usually doesn’t get to (and probably wouldn’t want to) witness? [23:30]
  • On the proximity of our superpowers to our wounds, and the double-bladed “edge” we fear losing by soothing those wounds. [28:29]
  • What’s behind Josh’s seeming inability to practice mediocrity? [30:55]
  • Where did my obsession with efficiency originate? [34:08]
  • How this efficiency has played into my attitude about competition, and why I’ve taken the last six months to hit the pause button on the sense of urgency they tend to generate and see if I’m pulled in a different direction. [39:38]
  • My relationship with control and the healing power of psychedelics. [43:10]
  • How exploration of the entanglement of overdevelopment and underdevelopment affect my aforementioned “edge.” [49:25]
  • Slow is smooth, and smooth is fast: the virtuoso can move slower than their opponent and still get there first. With mastery, more is accomplished with less effort. [52:36]
  • What discoveries have surfaced for me since hitting the pause button? [55:49]
  • What is the cave process, and how is it implemented? [59:53]
  • What advice might my 20-year-older self impart to me today? [1:03:19]
  • How should we best prepare for the world ahead if regular disruptive events — like the COVID-19 pandemic and exponentially ramping technology — become the new normal? [1:09:31]
  • What’s the single most important attribute I look for when debating if I’ll bring a new person into my circle of friends? [1:14:18]
  • Do I ever worry I’m mistaking noise for signal with learning from successful people, survival bias, and all that jazz? [1:15:23]
  • What have I learned about myself and the world since getting a dog? [1:16:46]
  • Parting thoughts. [1:18:26]