Derek Sivers — Finding Paths Less Traveled, Taking Giant Leaps, and Picking the Right “Game of Life”
Tim Ferriss Tim Ferriss
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 Published On Apr 21, 2023

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Resources from this episode: https://tim.blog/2023/04/21/derek-siv...

Derek 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!

00:00 Start
00:58 The Derek Sivers School of Enough.
5:33 Scuba diving in Iceland.
10:24 Categories we apply to ourselves and others.
17:15 Derek’s people compass.
22:59 How to secure your tech independence.
59:39 The un-optimized life.
1:11:21 The meaning of Derek’s upcoming book, Useful Not True.
1:28:10 The problem with moral relativism and other -isms.
1:47:21 Giant leaps.
1:56:55 Finding and asking mentors for help.
2:05:20 Games.
2:09:36 The wisdom of quitting when you’re ahead.
2:14:38 Why would Derek — never in need of external validation — seek fame?
2:18:24 What makes Derek so darned interesting?
2:21:00 Has Derek always been a satisficer?
2:30:06 Living on the edge case.
2:34:12 The real question behind “What would you tell your younger self?”
2:39:30 Giving directions in Antarctica.
2:40:31 How do you teach an 11-year-old to act like a 16-year-old?
2:45:04 Parting thoughts.

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

Tim Ferriss is one of Fast Company’s “Most Innovative Business People” and an early-stage tech investor/advisor in Uber, Facebook, Twitter, Shopify, Duolingo, Alibaba, and 50+ other companies. He is also the author of five #1 New York Times and Wall Street Journal bestsellers: The 4-Hour Workweek, The 4-Hour Body, The 4-Hour Chef, Tools of Titans and Tribe of Mentors. The Observer and other media have named him “the Oprah of audio” due to the influence of his podcast, The Tim Ferriss Show, which has exceeded 900 million downloads and been selected for “Best of Apple Podcasts” three years running.

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