Anne Lamott and Josh Waitzkin (#756)

This episode is a two-for-one, and that’s because the podcast recently hit its 10-year anniversary and passed one billion downloads. To celebrate, I’ve curated some of the best of the best—some of my favorites—from more than 700 episodes over the last decade. I could not be more excited. The episode features segments from episode #522 “Anne Lamott on Taming Your Inner Critic, Finding Grace, and Prayer” and #148: “Josh Waitzkin, The Prodigy Returns.”

Bios of guests may be found at tim.blog/combo.

Please enjoy!

Listen to the episode on Apple Podcasts, Spotify, Overcast, Podcast Addict, Pocket Casts, Castbox, YouTube, YouTube Music, Amazon Music, Audible, or on your favorite podcast platform.

This episode is brought to you by Momentous high-quality supplements, Helix Sleep premium mattresses, and Shopify global commerce platform, providing tools to start, grow, market, and manage a retail business.

Transcript for the full Anne Lamott episode | Transcript for the full Josh Waitzkin episode | Transcripts for all episodes

Listen onApple Podcasts

Listen onSpotify

Listen onOvercast

#756: Anne Lamott and Josh Waitzkin

This episode is brought to you by Helix Sleep! Helix was selected as the best overall mattress of 2025 by Forbes and Wired magazines and best in category by Good Housekeeping, GQ, and many others. With Helix, there’s a specific mattress to meet each and every body’s unique comfort needs. Just take their quiz—only two minutes to complete—that matches your body type and sleep preferences to the perfect mattress for you. They have a 10-year warranty, and you get to try it out for a hundred nights, risk-free. They’ll even pick it up from you if you don’t love it. And now, Helix is offering 20% off all mattress orders at HelixSleep.com/Tim.

This episode is brought to you by Momentous high-quality creatine! I’ve long benefitted from creatine for athletic and gym performance, and now I’m increasing my daily intake to enjoy the cognitive benefits as well. A pilot study in Alzheimer’s patients demonstrated that supplementing can increase brain creatine levels in just 8 weeks, improving measures of memory, reasoning, and attention. And a double-blind, placebo-controlled study found that creatine can restore aspects of memory and attention within hours in adults who are sleep deprived. I use Momentous Creatine made with Creapure®, which is sourced from Germany and has the strictest lab standards to ensure it’s at least 99.9% pure. And try Momentous’s Creatine Chews—clean chewable tablets with 1 gram of Creapure® creatine per chew—and their whey protein isolate and magnesium threonate, all of which meet their same, exacting standards. Check out Momentous for yourself and get 35% off your first subscription order with code TIM at LiveMomentous.com/Tim.

This episode is brought to you by Shopify! Shopify is one of my favorite platforms and one of my favorite companies. Shopify is designed for anyone to sell anywhere, giving entrepreneurs the resources once reserved for big business. In no time flat, you can have a great-looking online store that brings your ideas to life, and you can have the tools to manage your day-to-day and drive sales. Go to shopify.com/Tim to sign up for a one-dollar-per-month trial period. It’s a great deal for a great service, so I encourage you to check it out. Take your business to the next level today by visiting shopify.com/Tim.

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

SHOW NOTES

[04:49] Notes about this supercombo format.
[05:51] Enter Anne Lamott.
[06:21] What is it about Bird by Bird that has affected so many people so deeply?
[07:18] Where the title of Bird by Bird originated.
[09:40] How Neal Allen helps people tame (but not discard) their inner critic.
[10:45] Who controls the dial when you’re tuned in to KFKD radio?
[11:51] How Anne recommends I pursue my fiction writing aspirations.
[12:37] The pros and cons of Anne’s upbringing.
[19:08] What does being “spiritually fit” mean to Anne?
[24:40] How radical self-care became an imperative for Anne.
[32:25] The dark night that turned Anne’s son Sam’s life around.
[38:10] Enter Josh Waitzkin.
[38:43] On Dreaming Yourself Awake by B. Alan Wallace and Brian Hodel.
[39:58] Casual exercise.
[40:52] Josh’s terrifying experience with the Wim Hof method.
[45:52] How Josh uses “flow” as therapy.
[48:19] Initiating a flow state.
[50:45] Cognitive biases and armchair professors.
[55:07] Developing high-level sensitivity and listening to your senses.
[57:53] Strategies for on-boarding newcomers to mindfulness training.
[1:02:40] Paddlesurfers in peril.
[1:03:36] Embracing the funk.
[1:06:03] On parenting.
[1:15:07] Fixed perspectives and growth mindsets.
[1:17:34] On training somatic sensitivity.
[1:22:06] On mitigating the dangers of a fixed identity.
[1:24:32] Marcelo Garcia and the principle of cultivating quality as a way of life.
[1:30:19] Quality and presence in parenthood.
[1:33:42] The fire-walking process.
[1:40:11] Translating techniques learned from martial arts to less obvious activities (like investing).
[1:42:19] Building slack into the system.
[1:46:17] Scarcity in the learning process.
[1:54:27] Josh’s daily journaling process.
[1:56:25] Thematic interconnectedness in the context of education.
[2:04:08] The Art of Learning Project.
[2:05:59] Parting thoughts.