Think Better Soon: Chasing Failure, Gratitude, and the Questions That Reframe Life

Jason Newland and JP Bradley unpack a counterintuitive idea inspired by Ryan Leake: sometimes chasing failure can move you further than chasing success. They use that lens to explore self-awareness, negative self-talk, collaboration, gratitude, and why the only real failure is never trying.

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• Timestamps:(00:00) Opening the episode and the “chasing failure” premise(01:50) Ryan Leake’s background and why his story stood out(02:35) Cold-emailing every NBA team for a tryout(03:24) The Phoenix Suns say yes(04:20) The tryout, the rejection, and the documentary that followed(05:29) “Great learners ask better questions”(05:57) Question 1 - What’s it like to be on the other side of me?(08:29) Android vs iPhone as a funny example of relational friction(10:25) The assignment - ask 2 or 3 people and take notes(11:50) Question 2 - What story am I telling myself?(12:57) Stinking thinking and the repeated negative loop(14:05) Helping kids replace the worst-case story(15:09) Question 3 - What is my part to play?(16:47) Clear roles, collaboration, and fuzzy expectations(17:02) Question 4 - Who can I pave the way for?(18:15) Mentors, family, and investing in younger people(19:19) Question 5 - Am I enjoying it?(19:47) Gratitude determines enjoyment(20:51) Question 6 - What would I do if I knew I couldn’t fail?(21:21) Chasing the failure anyway(22:28) Shame, fear, and avoidance as the real trap(23:43) The parable of the talents and the fear of trying(24:12) Teddy Roosevelt and “the man in the arena”(24:50) Sarah Blakely’s dinner-table ritual around failure(25:45) The research-based correction - failure is not automatically a teacher(26:06) University of Chicago findings on failure feedback(27:01) Why “fail fast” can become lazy thinking in business(28:46) Learning from other people’s mistakes(29:03) Amy Edmondson’s 3 types of failure(30:03) Three conditions for healthy chasing(32:05) Reframing the whole idea - the chase is about what you learn(32:53) Weekly action steps from Jason and JP(35:20) Wise risk, recovery, and the one failure you can’t recover from(37:22) Closing reflection on the counterintuitive