#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”
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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.
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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Past guests on The Tim Ferriss Show include Jerry Seinfeld, Hugh Jackman, Dr. Jane Goodall, LeBron James, Kevin Hart, Doris Kearns Goodwin, Jamie Foxx, Matthew McConaughey, Esther Perel, <a href="https://t