#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 cr