#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”

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. * This episode is brought to you by Allbirds! Allbirds are incredibly comfortable shoes, sustainably made, with design rooted in simplicity. I’ve been wearing Allbirds for the last several months, and I’ve been alternating between two pairs. I started with the Tree Runners (in marine blue, if you’re curious), and now I’m wearing the Tree Dashers, and the Tree Dashers are my current “daily driver.” I stick with the blue hues, and the Dashers are in buoyant blue. The color pops, and I’ve received a ton of compliments. The Tree Dasher is an everyday running and walking shoe that’s also great for light workouts. It’s super comfortable, and I’ve been testing it on long walks in Austin and New Zealand on both trails and pavement. Find your perfect pair at Allbirds.com today and use code TIM for free socks with a purchase of $48 or more. Just add a pair of socks to your shopping cart and apply code TIM to make the pair free. * This episode is also brought to you by Shopify! Shopify is one of my favorite platforms and one of my favorite companies. Shopify is designed for anyone to sell anywhere, giving entrepreneurs the resources once reserved for big business. In no time flat, you can have a great-looking online store that brings your ideas to life, and you can have the tools to manage your day-to-day and drive sales. No coding or design experience required. Go to shopify.com/Tim to sign up for a one-dollar-per-month trial period. It’s a great deal for a great service, so I encourage you to check it out. Take your business to the next level today by visiting shopify.com/Tim. * This episode is also brought to you by Wealthfront! Wealthfront is an app that helps you save and invest your money. Right now, you can earn 4.3% APY—that’s the Annual Percentage Yield—with the Wealthfront Cash Account. That’s more than eleven times more interest than if you left your money in a savings account at the average bank, according to FDIC.gov.  It takes just a few minutes to sign up, and then you’ll immediately start earning 4.3% interest on your savings. And when you open an account today, you’ll get an extra fifty-dollar bonus with a deposit of five hundred dollars or more.  Visit Wealthfront.com/Tim to get started. * [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. * For show notes and past guests on The Tim Ferriss Show, please visit tim.blog/podcast. For deals from sponsors of The Tim Ferriss Show, please visit tim.blog/podcast-sponsors Sign up for Tim’s email newsletter (5-Bullet Friday) at tim.blog/friday. For transcripts of episodes, go to tim.blog/transcripts. Discover Tim’s books: tim.blog/books. Follow Tim: Twitter: twitter.com/tferriss  Instagram: instagram.com/timferriss YouTube: youtube.com/timferriss Facebook: facebook.com/timferriss  LinkedIn: linkedin.com/in/timferriss 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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