#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.


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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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.


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