Radical Doubt, Super Skepticism

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I think we should be skeptical of every ism, avoid ideology and take ideas, piecemeal. The more labels you apply to yourself, the stupider you get. Do you know Sonia Lombersky? No. Oh, she wrote one of those books on happiness after I read Stumbling on Happiness. And then finally a guide to the good 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.

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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.

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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.

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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.