#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 .css-j9qmi7{display:-webkit-box;display:-webkit-flex;display:-ms-flexbox;display:flex;-webkit-flex-direction:row;-ms-flex-direction:row;flex-direction:row;font-weight:700;margin-bottom:1rem;margin-top:2.8rem;width:100%;-webkit-box-pack:start;-ms-flex-pack:start;-webkit-justify-content:start;justify-content:start;padding-left:5rem;}@media only screen and (max-width: 599px){.css-j9qmi7{padding-left:0;-webkit-box-pack:center;-ms-flex-pack:center;-webkit-justify-content:center;justify-content:center;}}.css-j9qmi7 svg{fill:#27292D;}.css-j9qmi7 .eagfbvw0{-webkit-align-items:center;-webkit-box-align:center;-ms-flex-align:center;align-items:center;color:#27292D;}