Tim Ferriss

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!

Listen to the episode on Apple Podcasts, Spotify, Overcast, Stitcher, Castbox, Google Podcasts, or on your favorite podcast platform.

Brought to you by Wealthfront automated investing and Vuori comfortable and durable performance apparel.

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

This episode is brought to you by WealthfrontWealthfront is a financial services platform that offers services to help you save and invest your money. Right now, you can earn a 3.25% base APY—that’s the Annual Percentage Yield—with the Wealthfront Cash Account from its network of program banks. That’s nearly eight times more interest than an average savings account at a bank, according to FDIC.gov as of 12/15/2025 (Wealthfront’s 3.25% APY vs. 0.40% average savings rate). Right now, for a limited time, Wealthfront is offering new clients an additional 0.65% boost over the base rate for three months, meaning you can get 3.90% APY, limited to $150,000 in deposits. Terms & Conditions apply. Visit Wealthfront.com/Tim to get started. 

The Cash Account, which is not a deposit account, is offered by Wealthfront Brokerage LLC, member FINRA/SIPC. Wealthfront Brokerage is not a bank. The 3.25% Base APY on cash deposits is as of December 19, 2025, is representative, subject to change, and requires no minimum. If you are eligible for the overall boosted rate of 3.9% offered in connection with this promo, your boosted rate is also subject to change if the base rate decreases during the three-month promotional period. Tim Ferriss, who is not a client, receives cash compensation from Wealthfront Brokerage LLC for advertising and holds a non-controlling equity interest in the corporate parent of Wealthfront Brokerage LLC. This ad may not reflect the experience of other Cash Account clients, and similar outcomes are not guaranteed. See full disclosures here


This episode is brought to you by Vuori ClothingVuori is a new and fresh perspective on performance apparel, perfect if you are sick and tired of traditional, old workout gear. Get yourself some of the most comfortable and versatile clothing on the planet at VuoriClothing.com/Tim. Not only will you receive 20% off your first purchase, but you’ll also enjoy free shipping on any US orders over $75 and free returns.


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

SCROLL BELOW FOR LINKS AND SHOW NOTES…

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

SELECTED LINKS FROM THE EPISODE

  • Connect with Josh Waitzkin:

Website | The Art of Learning Project

SHOW NOTES

  • 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]

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Comment Rules: Remember what Fonzie was like? Cool. That's how we're gonna be — cool. Critical is fine, but if you're rude, we'll delete your stuff. Please do not put your URL in the comment text and please use your PERSONAL name or initials and not your business name, as the latter comes off like spam. Have fun and thanks for adding to the conversation! (Thanks to Brian Oberkirch for the inspiration.)

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Patrick M. Turner
Patrick M. Turner
4 years ago

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*#!

Raphael
Raphael
4 years ago

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…

Raphael
Raphael
4 years ago
Reply to  Raphael

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…

Kayla Reiter
Kayla Reiter
4 years ago

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.

Dora
Dora
4 years ago

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

Kayla Reiter
Kayla Reiter
4 years ago

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.

Angie R
Angie R
4 years ago

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!

tim mcauley
tim mcauley
4 years ago

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.

Tim

Chip Holcher
Chip Holcher
4 years ago

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

Matthew Z
Matthew Z
4 years ago

*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

shawnmuench1992
shawnmuench1992
4 years ago

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.


Coyote

A card game by Tim Ferriss and Exploding Kittens

COYOTE is an addictive card game of hilarity, high-fives, and havoc! Learn it in minutes, and each game lasts around 10 minutes.

For ages 10 and up (though I’ve seen six-year olds play) and three or more players, think of it as group rock, paper, scissors with many surprise twists, including the ability to sabotage other players. Viral videos of COYOTE have been watched more than 250 million times, and it’s just getting started.

Unleash your trickster spirit with a game that’s simple to learn, hard to master, and delightfully different every time you play. May the wit and wiles be with you!

Keep exploring.