Derek Sivers, Philosopher-Entrepreneur — The Greatest Year of His Life (#777)

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“Whatever you feel yourself leaning away from, try leaning into. If you hate opera, then go learn more about opera. And if you hate sports, well, then go learn more about sports. It’s usually just learning about something gives you an appreciation for this thing that you used to just dismiss.”
— Derek Sivers

Derek Sivers is an author of philosophy and entrepreneurship, known for his surprising, quotable insights and pithy, succinct writing style. Derek’s books (How to Live, Hell Yeah or No, Your Music and People, Anything You Want) and newest projects are at his website: sive.rs. His new book is Useful Not True.

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

The transcript of this episode can be found here. Transcripts of all episodes can be found here.

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#777: Derek Sivers, Philosopher-Entrepreneur — The Greatest Year of His Life

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Want to hear the last time Derek was on the show? Listen to our conversation here, in which we discuss the benefits of an unoptimized life, finding and asking mentors for help, the wisdom of quitting when you’re ahead, how to teach an 11-year-old to act like a 16-year-old, the problem with moral relativism and other -isms, securing tech independence, and much more.

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

SELECTED LINKS FROM THE EPISODE

Connect with Derek Sivers:

Website | Podcast | Twitter | YouTube

SHOW NOTES

[00:07:18] Derek Sivers: A Man who brings his own introduction.
[00:09:25] First mind change: Emirati coffee.
[00:12:34] Second mind change: Ruby to Python.
[00:13:54] Third mind change: Rats.
[00:17:23] Fourth mind change: China.
[00:23:24] Fifth mind change: Dubai.
[00:26:48] Tamashee: Come for the sandals, stay for the culture.
[00:30:52] Cormac McCarthy Writes to the Editor of The Santa Fe New Mexican.
[00:31:47] Shifting perspectives and the value of questioning preconceptions.
[00:51:23] Brian Eno and MusicThoughts.
[00:53:57] John Cage.
[00:56:34] Three glasses.
[00:57:08] Derek’s experimental housing project.
[01:03:51] Rich Hickey and practical applications of simplicity.
[01:29:20] Tyler Cowen.
[01:35:57] Inchword and language learning.
[01:46:35] Traveling to inhabit philosophies.
[01:54:14] Parting thoughts.

MORE DEREK SIVERS QUOTES FROM THE INTERVIEW

“Whatever you feel yourself leaning away from, try leaning into. If you hate opera, then go learn more about opera. And if you hate sports, well, then go learn more about sports. It’s usually just learning about something gives you an appreciation for this thing that you used to just dismiss.”
— Derek Sivers

“I travel to inhabit philosophies.”
— Derek Sivers

“Don’t jump through hoops to save taxes, jump through a hoop to go make more money. That’s the growth choice anyway. That’s the thought process that leads you to make growing decisions, not shrinking decisions.”
— Derek Sivers

“I’m willing to throw myself in and feel the pain to see if I’ve done it wrong.”
— Derek Sivers

“When I’m around people who I know agree with me, my inherent curiosity level drops a bit. And when I’m around people who I know don’t think like me, my curiosity piques.”
— Derek Sivers

“I deliberately fucked up my life and made a bunch of crazy fucking decisions, and some of them worked out great, and some of them didn’t. And I’m so happy that I did that.”
— Derek Sivers

“So often, the difference between success and failure is the mindset that leads you to take different actions. But if you just look at a situation, and you say, “That’s it. That’s what the situation is,” I’m not talking about physical things. I mean declaring something to be a dead end, declaring something to suck, these are all things of the mind, and nothing of the mind is necessarily true. Everything that’s just in the mind is just one perspective.”
— Derek Sivers

“It can be much harder to do something that is objectively simple, that stands alone, that isn’t dependent on other things. It can be harder to make that, but it’s ultimately usually a better choice because it’s more maintainable, it’s easier to change, it’s easier to stop and start. It’s simpler even if it’s harder to make.”
— Derek Sivers

“Esperanto is hippie Klingon.”
— Derek Sivers

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