#668: Derek Sivers — The Joys of an Un-Optimized Life, Finding Paths Less Traveled, Creating Tech Independence (and Risks of the Cloud), Taking Giant Leaps, and Picking the Right “Game of Life”

The Tim Ferriss Show

Apr 21 2023 • 2 hrs 54 mins

Brought to you by Allbirds incredibly comfortable shoes,Wealthfront high-yield savings account, and Shopify global commerce platform providing tools to start, grow, market, and manage a retail business.

Derek Sivers (@sivers) is an author of philosophy and entrepreneurship, known for his surprising, quotable insights and pithy, succinct writing style. He is a former musician, programmer, TED speaker, and circus clown, who sold his first company, CDBaby, for $22 million and gave all the money to charity.

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 upcoming book is Useful Not True.

Please enjoy!

P.S. To follow the exact step-by-step "Tech Independence" instructions from Derek, please visit sive.rs/ti.


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[06:16] The Derek Sivers School of Enough.

[11:24] Scuba diving and empathy lessons in Iceland.

[16:13] Categories we apply to ourselves and others.

[22:46] Derek’s people compass.

[28:14] How to secure your tech independence.

[1:05:19] The unoptimized life.

[1:16:37] The meaning of Derek’s upcoming book, Useful Not True.

[1:32:55] The problem with moral relativism and other -isms.

[1:51:24] Giant leaps.

[2:00:10] Finding and asking mentors for help.

[2:08:18] Games.

[2:12:26] The wisdom of quitting when you’re ahead.

[2:17:13] Why would Derek — never in need of external validation — seek fame?

[2:20:45] What makes Derek so darned interesting?

[2:23:18] Has Derek always been a satisficer?

[2:31:43] Living on the edge case.

[2:35:33] The real question behind “What would you tell your younger self?”

[2:40:29] Giving directions in Antarctica.

[2:41:46] How do you teach an 11-year-old to act like a 16-year-old?

[2:45:45] Parting thoughts.


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