#753: Derek Sivers and Kevin Kelly

This episode is a two-for-one, and that’s because the podcast recently hit its 10-year anniversary and passed one billion downloads. To celebrate, I’ve curated some of the best of the best—some of my favorites—from more than 700 episodes over the last decade. I could not be more excited. The episode features segments from episode "Derek Sivers on Developing Confidence, Finding Happiness, and Saying No to Millions" and "Interview of Kevin Kelly, Co-Founder of WIRED, Polymath, Most Interesting Man In The World?" Please enjoy! Sponsors: Wealthfront high-yield cash account: https://Wealthfront.com/Tim (Start earning 5.00% APY on your short-term cash until you’re ready to invest. And when you open an account today, you can get an extra fifty-dollar bonus with a deposit of five hundred dollars or more.) Terms apply. Helix Sleep premium mattresses: https://HelixSleep.com/Tim (25–30% off all mattress orders and two free pillows) AG1 all-in-one nutritional supplement: https://DrinkAG1.com/Tim (1-year supply of Vitamin D (and 5 free AG1 travel packs) with your first subscription purchase.) Timestamps: [00:00] Start [05:47] Notes about this supercombo format. [06:50] Enter Derek Sivers. [07:20] From pig show busker to circus ringleader. [10:42] Derek's framework for developing confidence. [13:05] "The standard pace is for chumps." [18:51] Relaxing for the same result. [24:01] The origins of "HELL YEAH! or no." [26:25] "Busy" implies a life out of control. [28:03] What inspired the automation of CD Baby? [33:22] Derek's billboard. [34:32] Good advice at any age: "Don't be a donkey." [40:24] Enter Kevin Kelly. [41:02] Kevin's biggest regret. [43:13] Finding contentment in minimalism and "voluntary simplicity" without starving to death. [50:33] Kevin's epiphany when he embraced writing as a late bloomer. [56:40] Why Kevin promised himself he would never resort to teaching English while traveling abroad. [59:07] Finding purpose through resilience and the creator's dilemma. [1:06:50] Why the appeal of being a billionaire is overrated. [1:11:05] Middle-aged optimization. [1:15:28] Realizations following a "six months until death" challenge. [1:20:08] Kevin's Kickstarter-funded project linking angels and robots. [1:22:41] Why a self-proclaimed ex-hippie waited until his 50th birthday to try LSD for the first time. [1:28:43] Why a population implosion is probable in the next 100 years. [1:36:05] The greatest gift you can give to your child. [1:38:21] The criteria for Amish technology assimilation. [1:45:03] What technology-free sabbaticals can do for you. [1:48:53] Long Now Foundation's vision of a better civilization. [1:53:33] The graphic novel teaching young people how to become indispensable. [1:54:52] An antidote to misguided "follow your passion" advice. [1:56:44] Kevin's favorite fiction book. [1:59:15] The resource Kevin compiled for documentary lovers. [2:02:47] A name Kevin considers synonymous with "success" (and why success is overrated). [2:05:46] What Kevin would change about himself. [2:07:59] Daily rituals. [2:10:44] How Kevin accumulated enough books to fill a two-story library. [2:15:19] How Adam Savage from MythBusters transformed Kevin's method of organization. [2:17:14] The project everyone should undertake at least once in life. [2:19:30] Does discovery equal invention? [2:20:12] Kevin's advice to his younger self. [2:23:16] 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. 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