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

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Feb 16, 2021

Josh Waitzkin, an eight-time national chess champion and author of "The Art of Learning," dives into the depths of mastering skills and personal growth. He discusses the transformative power of questioning assumptions and how ‘gating questions’ can enhance critical thinking. The conversation touches on balancing personal quirks with performance excellence and the journey of embracing strengths alongside weaknesses. Josh also reflects on introspection in martial arts, highlighting the necessity of understanding deeper principles as we navigate uncertain futures.

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ADVICE

Exposing Assumptions

Ask people what assumptions they are making about their plans or goals.
This reveals how rigorously they've examined their ideas.

ADVICE

The No-Brainer Test

When evaluating an idea, ask if pursuing it is a no-brainer, even with diminished rewards.
This assesses intrinsic motivation and resilience to unforeseen challenges.

ADVICE

Testing Assumptions

Prioritize cheap, fast experiments to test assumptions about potential upsides and downsides.
Look for comparable cases and speak to those involved.

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