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

“I think of learning as unobstructed self-expression.”
— Josh Waitzkin

Josh Waitzkin, author of The Art of Learning: An Inner Journey to Optimal Performance, is an eight-time US 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 12 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. 

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


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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 conversation with Josh Waitzkin?In this episode (his most recent previous appearance on The Tim Ferriss Show), we discussed cramming two months of learning into one day, what Ernest Hemingway and Marcelo Garcia could teach us about letting go, the mediocrity of the “simmering six,” and lots more. (Stream below or right-click here to download):

#375: Josh Waitzkin — How to Cram 2 Months of Learning into 1 Day



  • Connect with Josh Waitzkin:

Website | The Art of Learning Project


  • What is Josh’s history with chess Grandmaster Maurice Ashley, and how have their shared and individual ideas about assumptions and shared constructs changed in the past 20 years? [04:45]
  • How Josh’s approach to learning differs from his friend and fellow athlete Dan Caulfield. [10:16]
  • What is foil boarding, and how does it overcome the conditions that restrict traditional surfing in a way that makes it a metaphor for Josh’s relationship to learning? [11:38]
  • eFoiling, one-wheeling, and the importance of learning how to fall safely. [13:14]
  • Foils and boils: practicing the art of falling from a practical vs. an Instagram-ready standpoint. [15:37]
  • How volunteering to care for people going through difficult psychedelic experiences at a music festival was my version of learning to navigate boils. In both cases, we’re really practicing the ability to be comfortable around extraordinary circumstances in order to fully experience what follows. [18:49]
  • How designing a learning process around the meta can build skills applicable to countless circumstances — and why an observer with a lifetime of surfing under their belt might consider Josh’s approach to learning the craft odd. [22:16]
  • The benefits of being a beginner. [26:10]
  • Josh says: “The internal spirit is the teacher or myself 20 years from now.” What does he mean by this? [32:44]
  • What young Tim once learned from talking to an old Tim at a ski lodge fireside, and why asking for advice from another version of one’s self is a worthwhile thought exercise. [36:02]
  • A short retelling of the time Josh almost died doing Wif Hof breathing in a swimming pool, how surviving the event inspired the way he and his family live now. [39:58]
  • Writing exercises that have gotten me in the mindset — without putting myself in actual danger — to make decisions under the weight of imminent mortality. [42:02]
  • “Firewalking” with Josh: How to physiologically embody something we’re trying to learn in a way that mere observation can’t instill. [43:38]
  • The importance of feedback loops and the game-changing difference it can make to have them on tap in unlimited, accurate doses. Can Josh tell me about the feedback loops he consults in his own life without referring to foiling in some capacity? When might he not want to reflect on the scrutiny of a feedback loop? [46:59]
  • When a coach or trainer’s feedback might be counterproductive. [53:39]
  • As someone who isolates himself by design except for interactions with employees, family, and friends and doesn’t rely on social media, how does Josh stress-test the integrity of his own thinking and positions? [55:10]
  • To separate the wheat from the chaffe of your ideas, cultivate a close ecosystem of people you can trust to be honest with you in their pushback — or a partner whose thought processes complement rather than compliment your own. [58:54]
  • Examining the confidence that Josh describes as being “a little bit crazy and messianic” in the character of many high-acheivers who seem to chart a record of success regardless of the opinion of their lessers — like nine-time BJJ World Champion Marcelo Garcia. [1:00:24]
  • The unexpected rewards of approaching skill acquisition in an unorthodox way: when Josh and Dan’s eFoil training translated to foil as they expected — and as none of the “experts” would have. [1:03:37]
  • I offer some pushback on the point that Josh would have rejected the notion of that translation if he had stress-tested it. [1:05:17]
  • Reps hidden in plain sight. [1:05:46]
  • In what other arts — chess, BJJ, push hands, or investing — might reps be similarly hidden in plain sight or lend themselves to deliberate practice? [1:07:30]
  • Conceptual or thematic reps hidden in plain sight. [1:09:02]
  • Of course Josh’s method of teaching my girlfriend and me how to surf flies in the face of how most instructors would do it. I think it also happens to be right — and in line with the empathetic methods of another exceptional coach I know, Kelly Starrett. [1:10:04]
  • Who is Robert Kegan, and why is he interesting to Josh? [1:15:29]
  • Parting thoughts. [1:18:35]