How to Find the Mindsets that Work For You (ft. Derek Sivers)

I’ve got a special episode for you today. I sat down in person with my longtime friend and first-ever podcast guest, Derek Sivers. We haven’t recorded live before, and honestly, it shows—in the best way. It’s raw, weird, and filled with the kind of conversations we usually when we’re just hanging out together.

We dig into Derek’s new book Useful, Not True, and the big idea behind it: that our beliefs don’t need to be true to be helpful. That spins off into everything from remixing creative influences (metal + Dixieland jazz, anyone?) to why most podcasts—including mine—have gotten painfully predictable. We talk artistic reinvention, Bob Dylan, Bowie, Miles Davis, why most “thought leaders” are just regurgitating each other’s ideas, and why I'm ending the podcast as you know it—and what’s next!

We also dive into the deeper stuff: the emotional power of belief, authenticity vs. performative vulnerability, therapy culture, and why sometimes the most liberating thing you can do is reject what everyone else thinks is necessary—relationships, kids, all of it.

This was one of the most honest, meandering, and creatively energizing conversations I’ve had in a while. If you’re into big questions, unconventional ideas, and the occasional musical metaphor, this one’s for you.

Derek’s new book- Useful, Not True: https://www.amazon.com/Useful-Not-Tru...

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Chapters:

0:00 Intro
0:58 Where Derek finds inspiration
15:59 The Power of Cross-Pollinating Ideas
19:25 Biggest perspectival shifts
25:28 Why do so many perspectives feel true even though they are not necessarily true?
31:12 The Importance of Beliefs
36:14 How to fight through emotional resistance
38:32 Therapy culture
45:07 Nihilism
49:01 Feelings Matter
55:46 On Jordan Peterson and moral absolutism
1:03:20 Derek's relationship struggles
1:15:11 Is it useful to not have a relationship?
1:18:05 Social norms and dating
1:20:42 The importance of having a supportive community


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