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.

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The transcript of this episode can be found here. Transcripts of all episodes can be found here.

#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]


The Tim Ferriss Show is one of the most popular podcasts in the world with more than 900 million downloads. It has been selected for "Best of Apple Podcasts" three times, it is often the #1 interview podcast across all of Apple Podcasts, and it's been ranked #1 out of 400,000+ podcasts on many occasions. To listen to any of the past episodes for free, check out this page.

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

  1. Just an FYI Tim; I read the 4 hour workweek in July of 2020 and after 40 years of the grind and a month after turning 60, retirement is a mere 18 working days away. I’ve set up a consulting gig for a day a week for as long as I want it and re-started oil painting that I paused 35 years ago and it’s already a fun side gig that I can enjoy when it’s not a good day to golf. Travelling “apres covid” is also on deck and ready to pull that trigger too starting with Tuscany……all from listening to one book on the drive and from work for a week! Thanks for the kick in the a*#!

    1. You need to become a dad, that will definitely help you to step out of your head. You can be the director of how many companies as you want, it won’t mean nothing compared to being the dad of one single little person…

      1. Grammatically correct version of my comment!!
        You need to become a dad, that will definitely help you step out of your head. You can be the director of as many companies as you want, it won’t mean anything compared to being the dad of one single little person…

  2. I think your next jungle visit should be downhill and nordic skiing and hot springs/river sitting and coming to kettlebell flow and yoga with me in Breckenridge.

  3. My name is Dora and I am a foreign language teacher based in Athens, Greece. I am running a successful foreign language learning blog which is steadily growing.
    Since I have been an avid supporter and fan of your site for years and truly believe that both our sites have the same target audience, I would like to collaborate with you through affiliate marketing.
    What are your terms and conditions so that I could mention your website in one of my articles and get my readers able to be redirected to yours?
    Please, excuse my “illeterate” email on this issue but this is the very first email I write concerning such issue,
    However, I would like to whole-heartedly thank you for providing me with the opportunity to communicate with you,

    P.S. Respecting your rules I am not writing down the url or my company’s name

  4. I think you would love time in Summit because people are so great at prioritizing play here. We can get stoned and drink coffee and run up a mountain and go skiing and then drink wine and write by the fire and you can rewrite your book. I also had a suicide attempt in college and have had 9 concussions that make some things a little extra struggly, but I would love to how you around and talk about it.

  5. This was a beautiful episode. I’m a newer listener (I heard your episode with Brene’ Brown) and it’s been really interesting to hear the different tones of the episodes. I’m less interested in being the “best” at something and much more intrigued by the self-reflection, growth, and insight into your guests’ (or yours, as most of this episode seemed) story. Thank you!

  6. Loving everything about this episode. Very Monomyth Hero-journey-esque. I love when you two get together and talk.

    Glad to hear you’re hitting pause and seeing what emerges. Surrender is a wonderful thing.

    You mentioned processing childhood trauma…

    ….if you haven’t already checked out the book “Complex PTSD” by Pete Walker, please do.

    His take on the process of metabolizing the experience and how to get out of Flashbacks is very helpful, and will help you create a framework to process it faster and better.

    Thanks for doing what you do.

    Love your work.


  7. Tim –

    In the episode with Josh Waitzkin, you discussed the insight that you gleaned about how to love from raising Molly. Very cool! I wish you could bottle that up and inject it into everyone that chooses to raise a dog or any pet. So many people (and pets) could benefit. I train our dog to hunt (upland and waterfowl birds) and the unspoken bond that develops is amazing and instinctual.

    Mainly, our dog is an integral part of our everyday life. I was walking him while listening to this episode! I’m also glad to have evolved beyond my early training methods. As you noted – clarity is paramount. Still lots to learn but thankfully for our pups, we learned and love! Thanks for everything you do to help others.

    Chip H

  8. *Follow up Podcast suggestion*

    Tim, I finished this episode last night and thoroughly enjoyed it! I appreciated your explanations of psychedelic ego-erosion and the importance of meta learning.

    Coincidentally, I just started a podcast featuring longtime Grateful Dead roadie Steve Parish. He beautifully expounds on his experiences with psychedelic use as a catalyst for knowledge sharing/skill acquisition in a community setting. I thought you and your listeners would be interested in his tales of psychedelic driven renaissance.

    No Simple Road, Episode 139 “Story Time with Big Steve Parish.” The conversation starts around 33:30. Available on Spotify.

    Be well,

    Matthew Z
    North Carolina, USA

  9. Tim, (or anyone!) if you see this– there’s a trilogy (and I only recommend the trilogy) by Jed McKenna that sounds perfect for you right now. Eventually cashes out into human adulthood and undoing etc. I can’t detail my engagement with esoterica in a way that would show my recommendation is worth pursuing– but a few years incubating the stuff and it’s the more durable I’ve read.