#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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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.
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.
[2:12:26] 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, Elizabeth Gilbert, Terry Crews, Sia, Yuval Noah Harari, Malcolm Gladwell, Madeleine Albright, Cheryl Strayed, Jim Collins, Mary Karr, Maria Popova, Sam Harris, Michael Phelps, Bob Iger, Edward Norton, Arnold Schwarzenegger, Neil Strauss, Ken Burns, Maria Sharapova, Marc Andreessen, Neil Gaiman, Neil de Grasse Tyson, Jocko Willink, Daniel Ek, Kelly Slater, Dr. Peter Attia, Seth Godin, Howard Marks, Dr. Brené Brown, Eric Schmidt, Michael Lewis, Joe Gebbia, Michael Pollan, Dr. Jordan Peterson, Vince Vaughn, Brian Koppelman, Ramit Sethi, Dax Shepard, Tony Robbins, Jim Dethmer, Dan Harris, Ray Dalio, Naval Ravikant, Vitalik Buterin, Elizabeth Lesser, Amanda Palmer, Katie Haun, Sir Richard Branson, Chuck Palahniuk, Arianna Huffington, Reid Hoffman, Bill Burr, Whitney Cummings, Rick Rubin, Dr. Vivek Murthy, Darren Aronofsky, Margaret Atwood, Mark Zuckerberg, Peter Thiel, Dr. Gabor Maté, Anne Lamott, Sarah Silverman, Dr. Andrew Huberman, and many more.