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#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”

The Tim Ferriss Show

Tim Ferriss is a self-experimenter and bestselling author, best known for The 4-Hour Workweek, which has been translated into 40+ languages. Newsweek calls him "the world's best human guinea pig," and The New York Times calls him "a cross between Jack Welch and a Buddhist monk." In this show, he deconstructs world-class performers from eclectic areas (investing, chess, pro sports, etc.), digging deep to find the tools, tactics, and tricks that listeners can use.

Brought to you by <a href="http://allbirds.com" rel="noopener noreferrer" target="_blank">Allbirds</a> incredibly comfortable shoes, <a href="http://wealthfront.com/tim" rel="noopener noreferrer" target="_blank">Wealthfront</a> high-yield savings account, and <a href="http://shopify.com/tim" rel="noopener noreferrer" target="_blank">Shopify</a> global commerce platform providing tools to start, grow, market, and manage a retail business. Derek Sivers (<a href="https://twitter.com/sivers" rel="noopener noreferrer" target="_blank">@sivers</a>) 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: <a href="http://sive.rs/" rel="noopener noreferrer" target="_blank">sive.rs</a>. His upcoming book is <a href="https://sive.rs/u" rel="noopener noreferrer" target="_blank">Useful Not True</a>.Please enjoy!P.S. To follow the exact step-by-step "Tech Independence" instructions from Derek, please visit <a href="https://sive.rs/ti" rel="noopener noreferrer" target="_blank">sive.rs/ti</a>.*This episode is brought to you by <a href="http://Allbirds.com" rel="noopener noreferrer" target="_blank">Allbirds</a>! <a href="http://Allbirds.com" rel="noopener noreferrer" target="_blank">Allbirds</a> are incredibly comfortable shoes, sustainably made, with design rooted in simplicity. I’ve been wearing <a href="http://Allbirds.com" rel="noopener noreferrer" target="_blank">Allbirds</a> 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 <a href="http://Allbirds.com" rel="noopener noreferrer" target="_blank">Allbirds.com</a> 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 <a href="http://shopify.com/tim" rel="noopener noreferrer" target="_blank">Shopify</a>! <a href="http://shopify.com/tim" rel="noopener noreferrer" target="_blank">Shopify</a> is one of my favorite platforms and one of my favorite companies. <a href="http://shopify.com/tim" rel="noopener noreferrer" target="_blank">Shopify</a> 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 <a href="http://shopify.com/tim" rel="noopener noreferrer" target="_blank">shopify.com/Tim</a> 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 <a href="http://shopify.com/tim" rel="noopener noreferrer" target="_blank">shopify.com/Tim</a>.*This episode is also brought to you by <a href="http://wealthfront.com/tim" rel="noopener noreferrer" target="_blank">Wealthfront</a>! 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 <a href="http://wealthfront.com/tim" rel="noopener noreferrer" target="_blank">Wealthfront Cash Account</a>. 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 <a href="http://wealthfront.com/tim" rel="noopener noreferrer" target="_blank">an extra fifty-dollar bonus</a> with a deposit of five hundred dollars or more.  Visit <a href="http://wealthfront.com/tim" rel="noopener noreferrer" target="_blank">Wealthfront.com/Tim</a> to get started.*For show notes and past guests on <a href="http://tim.blog/podcast" rel="noopener noreferrer" target="_blank">The Tim Ferriss Show</a>, please visit <a href="https://tim.blog/podcast/?utm_source=podcast&utm_medium=podcast&utm_campaign=podcast-description" rel="noopener noreferrer" target="_blank">tim.blog/podcast</a>.For deals from sponsors of <a href="http://tim.blog/podcast" rel="noopener noreferrer" target="_blank">The Tim Ferriss Show</a>, please visit <a href="http://tim.blog/podcast-sponsors" rel="noopener noreferrer" target="_blank">tim.blog/podcast-sponsors</a>Sign up for Tim’s email newsletter (5-Bullet Friday) at <a href="https://go.tim.blog/5-bullet-friday-1/" rel="noopener noreferrer" target="_blank">tim.blog/friday</a>.For transcripts of episodes, go to <a href="http://tim.blog/transcripts" rel="noopener noreferrer" target="_blank">tim.blog/transcripts</a>.Discover Tim’s books: <a href="http://tim.blog/books" rel="noopener noreferrer" target="_blank">tim.blog/books</a>.Follow Tim:Twitter: <a href="https://twitter.com/tferriss" rel="noopener noreferrer" target="_blank">twitter.com/tferriss</a> Instagram: <a href="https://instagram.com/timferriss/" rel="noopener noreferrer" target="_blank">instagram.com/timferriss</a>YouTube: <a href="https://www.youtube.com/timferriss" rel="noopener noreferrer" target="_blank">youtube.com/timferriss</a>Facebook: <a href="https://www.facebook.com/TimFerriss/" rel="noopener noreferrer" target="_blank">facebook.com/timferriss</a> LinkedIn: <a href="http://linkedin.com/in/timferriss" rel="noopener noreferrer" target="_blank">linkedin.com/in/timferriss</a>Past guests on <a href="http://tim.blog/podcast" rel="noopener noreferrer" target="_blank">The Tim Ferriss Show</a> include <a href="https://tim.blog/2020/12/08/jerry-seinfeld/" rel="noopener noreferrer" target="_blank">Jerry Seinfeld</a>, <a href="https://tim.blog/2020/06/26/hugh-jackman/" rel="noopener noreferrer" target="_blank">Hugh Jackman</a>, <a href="https://tim.blog/2020/04/16/jane-goodall/" rel="noopener noreferrer" target="_blank">Dr. Jane Goodall</a>, <a href="https://tim.blog/2018/11/27/lebron-james-mike-mancias/" rel="noopener noreferrer" target="_blank">LeBron James</a>, <a href="https://tim.blog/2020/05/20/kevin-hart/" rel="noopener noreferrer" target="_blank">Kevin Hart</a>, <a href="https://tim.blog/2018/09/07/doris-kearns-goodwin-leadership/" rel="noopener noreferrer" target="_blank">Doris Kearns Goodwin</a>, <a href="https://tim.blog/2015/12/06/jamie-foxx/" rel="noopener noreferrer" target="_blank">Jamie Foxx</a>, <a href="https://tim.blog/2020/10/19/matthew-mcconaughey/" rel="noopener noreferrer" target="_blank">Matthew McConaughey</a>, <a href="https://tim.blog/2017/05/21/esther-perel/" rel="noopener noreferrer" target="_blank">Esther Perel</a>, <a href="https://tim.blog/2020/05/08/elizabeth-gilbert/" rel="noopener noreferrer" target="_blank">Elizabeth Gilbert</a>, <a href="https://tim.blog/2017/12/20/terry-crews-how-to-have-do-and-be-all-you-want/" rel="noopener noreferrer" target="_blank">Terry Crews</a>, <a href="https://tim.blog/2020/08/12/sia/" rel="noopener noreferrer" target="_blank">Sia</a>, <a href="https://tim.blog/2020/10/27/yuval-noah-harari/" rel="noopener noreferrer" target="_blank">Yuval Noah Harari</a>, <a href="https://tim.blog/2016/06/21/malcolm-gladwell/" rel="noopener noreferrer" target="_blank">Malcolm Gladwell</a>, <a href="https://tim.blog/2020/05/27/secretary-madeleine-albright/" rel="noopener noreferrer" target="_blank">Madeleine Albright</a>, <a href="https://tim.blog/2017/03/30/cheryl-strayed/" rel="noopener noreferrer" target="_blank">Cheryl Strayed</a>, <a href="https://tim.blog/2019/02/18/jim-collins/" rel="noopener noreferrer" target="_blank">Jim Collins</a>, <a href="https://tim.blog/2020/11/11/mary-karr/" rel="noopener noreferrer" target="_blank">Mary Karr,</a> <a href="https://tim.blog/2014/10/21/brain-pickings/" rel="noopener noreferrer" target="_blank">Maria Popova</a>, <a href="https://tim.blog/2020/05/15/sam-harris-2/" rel="noopener noreferrer" target="_blank">Sam Harris</a>, <a href="https://tim.blog/2021/01/21/michael-phelps-grant-hackett/" rel="noopener noreferrer" target="_blank">Michael Phelps</a>, <a href="https://tim.blog/2020/01/16/bob-iger/" rel="noopener noreferrer" target="_blank">Bob Iger</a>, <a href="https://tim.blog/2019/10/31/edward-norton-motherless-brooklyn/" rel="noopener noreferrer" target="_blank">Edward Norton</a>, <a href="https://tim.blog/2015/02/02/arnold-schwarzenegger/" rel="noopener noreferrer" target="_blank">Arnold Schwarzenegger</a>, <a href="https://tim.blog/2014/06/24/neil-strauss/" rel="noopener noreferrer" target="_blank">Neil Strauss</a>, <a href="https://tim.blog/2019/09/12/ken-burns/" rel="noopener noreferrer" target="_blank">Ken Burns</a>, <a href="https://tim.blog/2017/08/26/maria-sharapova/" rel="noopener noreferrer" target="_blank">Maria Sharapova</a>, <a href="https://tim.blog/2016/05/29/marc-andreessen/" rel="noopener noreferrer" target="_blank">Marc Andreessen</a>, <a href="https://tim.blog/2019/03/28/neil-gaiman/" rel="noopener noreferrer" target="_blank">Neil Gaiman</a>, <a href="https://tim.blog/2019/10/03/neil-degrasse-tyson/" rel="noopener noreferrer" target="_blank">Neil de Grasse Tyson</a>, <a href="https://tim.blog/2016/09/21/jocko-willink-on-discipline-leadership-and-overcoming-doubt/" rel="noopener noreferrer" target="_blank">Jocko Willink</a>, <a href="https://tim.blog/2020/12/03/daniel-ek/" rel="noopener noreferrer" target="_blank">Daniel Ek</a>, <a href="https://tim.blog/2020/09/08/kelly-slater/" rel="noopener noreferrer" target="_blank">Kelly Slater</a>, <a href="https://tim.blog/2019/11/27/peter-attia-fasting-metformin-longevity/" rel="noopener noreferrer" target="_blank">Dr. Peter Attia</a>, <a href="https://tim.blog/2016/02/10/seth-godin/" rel="noopener noreferrer" target="_blank">Seth Godin</a>, <a href="https://tim.blog/2018/09/25/howard-marks/" rel="noopener noreferrer" target="_blank">Howard Marks</a>, <a href="https://tim.blog/2020/02/06/brene-brown-striving-self-acceptance-saving-marriages/" rel="noopener noreferrer" target="_blank">Dr. Brené Brown</a>, <a href="https://tim.blog/2019/04/09/eric-schmidt/" rel="noopener noreferrer" target="_blank">Eric Schmidt</a>, <a href="https://tim.blog/2020/05/01/michael-lewis/" rel="noopener noreferrer" target="_blank">Michael Lewis</a>, <a href="https://tim.blog/2018/03/08/joe-gebbia-co-founder-of-airbnb/" rel="noopener noreferrer" target="_blank">Joe Gebbia</a>, <a href="https://tim.blog/2018/05/06/michael-pollan-how-to-change-your-mind/" rel="noopener noreferrer" target="_blank">Michael Pollan</a>, <a href="https://tim.blog/2021/03/01/jordan-peterson/" rel="noopener noreferrer" target="_blank">Dr. Jordan Peterson</a>, <a href="https://tim.blog/2017/05/31/vince-vaughn/" rel="noopener noreferrer" target="_blank">Vince Vaughn</a>, <a href="https://tim.blog/2020/04/23/brian-koppelman/" rel="noopener noreferrer" target="_blank">Brian Koppelman</a>, <a href="https://tim.blog/2019/05/07/ramit-sethi/" rel="noopener noreferrer" target="_blank">Ramit Sethi</a>, <a href="https://tim.blog/2020/11/18/dax-shepard/" rel="noopener noreferrer" target="_blank">Dax Shepard</a>, <a href="https://tim.blog/2014/10/15/money-master-the-game/" rel="noopener noreferrer" target="_blank">Tony Robbins</a>, <a href="https://tim.blog/2020/05/18/jim-dethmer/" rel="noopener noreferrer" target="_blank">Jim Dethmer</a>, <a href="https://tim.blog/2020/11/19/dan-harris/" rel="noopener noreferrer" target="_blank">Dan Harris</a>, <a href="https://tim.blog/2017/09/13/ray-dalio/" rel="noopener noreferrer" target="_blank">Ray Dalio</a>, <a href="https://tim.blog/2015/08/18/the-evolutionary-angel-naval-ravikant/" rel="noopener noreferrer" target="_blank">Naval Ravikant</a>, <a href="https://tim.blog/2021/03/08/vitalik-buterin-naval-ravikant/" rel="noopener noreferrer" target="_blank">Vitalik Buterin</a>, <a href="https://tim.blog/2021/03/16/elizabeth-lesser/" rel="noopener noreferrer" target="_blank">Elizabeth Lesser</a>, <a href="https://tim.blog/2019/04/18/amanda-palmer-2/" rel="noopener noreferrer" target="_blank">Amanda Palmer</a>, <a href="https://tim.blog/2021/02/18/katie-haun/" rel="noopener noreferrer" target="_blank">Katie Haun</a>, <a href="https://tim.blog/2017/10/09/richard-branson/" rel="noopener noreferrer" target="_blank">Sir Richard Branson</a>, <a href="https://tim.blog/2020/09/02/chuck-palahniuk/" rel="noopener noreferrer" target="_blank">Chuck Palahniuk</a>, <a href="https://tim.blog/2017/10/18/arianna-huffington/" rel="noopener noreferrer" target="_blank">Arianna Huffington</a>, <a href="https://tim.blog/2015/08/31/the-oracle-of-silicon-valley-reid-hoffman-plus-michael-mccullough/" rel="noopener noreferrer" target="_blank">Reid Hoffman</a>, <a href="https://tim.blog/2017/09/17/bill-burr/" rel="noopener noreferrer" target="_blank">Bill Burr</a>, <a href="https://tim.blog/2015/06/26/whitney-cummings/" rel="noopener noreferrer" target="_blank">Whitney Cummings</a>, <a href="https://tim.blog/2015/05/15/rick-rubin/" rel="noopener noreferrer" target="_blank">Rick Rubin</a>, <a href="https://tim.blog/2020/03/26/vivek-murthy/" rel="noopener noreferrer" target="_blank">Dr. Vivek Murthy</a>, <a href="https://tim.blog/2017/09/09/darren-aronofsky/" rel="noopener noreferrer" target="_blank">Darren Aronofsky</a>, <a href="https://tim.blog/2022/02/22/margaret-atwood/" rel="noopener noreferrer" target="_blank">Margaret Atwood</a>, <a href="https://tim.blog/2022/03/24/mark-zuckerberg/" rel="noopener noreferrer" target="_blank">Mark Zuckerberg</a>, <a href="https://tim.blog/2014/09/09/peter-thiel/" rel="noopener noreferrer" target="_blank">Peter Thiel</a>, <a href="https://tim.blog/2018/02/20/gabor-mate/" rel="noopener noreferrer" target="_blank">Dr. Gabor Maté</a>, <a href="https://tim.blog/2021/07/09/anne-lamott/" rel="noopener noreferrer" target="_blank">Anne Lamott</a>, <a href="https://tim.blog/2022/01/12/sarah-silverman/" rel="noopener noreferrer" target="_blank">Sarah Silverman</a>, <a href="https://tim.blog/2021/07/06/andrew-huberman/" rel="noopener noreferrer" target="_blank">Dr. Andrew Huberman</a>, and many more.See Privacy Policy at <a href="https://art19.com/privacy" rel="noopener noreferrer" target="_blank">https://art19.com/privacy</a> and California Privacy Notice at <a href="https://art19.com/privacy#do-not-sell-my-info" rel="noopener noreferrer" target="_blank">https://art19.com/privacy#do-not-sell-my-info</a>.

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-sponsorsSign 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/timferrissYouTube: youtube.com/timferrissFacebook: facebook.com/timferriss LinkedIn: linkedin.com/in/timferrissPast 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.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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#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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