Courage Over Confidence

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 #366 "Neil Gaiman — The Interview I've Waited 20 Years to Do" and episode #214 "How to Design a Life — Debbie Millman."

Please enjoy!

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Timestamps:

[00:00] Start

[05:11] Notes about this supercombo format.

[06:14] Enter Neil Gaiman.

[06:44] What Ian Fleming taught Neil about writing — even when he doesn't want to.

[09:56] Neil's biggest rule for writing.

[12:41] Neil's process for writing first drafts.

[14:30] What Neil aims to accomplish with his second drafts.

[14:40] Something Neil noticed when he first started writing and editing with the use of computers.

[17:27] Notebooks Neil prefers for writing first drafts.

[21:56] Fountain pens Neil has known and loved.

[22:57] How Neil's default writing time has changed over the years.

[24:56] The value of the Groundhog Day routine.

[26:24] Today's methods may not be tomorrow's.

[27:53] Lessons learned from Terry Pratchett.

[29:22] Parting thoughts and gratitude.

[31:21] Enter Debbie Millman.

[31:45] How Debbie describes her diverse background to new acquaintances.

[33:38] A childhood drawing predicting Debbie's future.

[37:54] Debbie's unintentional path to becoming a designer.

[45:41] Overcoming initial rejection.

[50:04] Debbie's advice to her college self after that first major rejection.

[54:25] Empathy vs. feeling slighted by those who reject us.

[59:28] Manhattan's influence on Debbie's pursuit of happiness and career.

[1:06:42] Debbie's abuse history and its impact on her self-sufficiency and charitable work.

[1:12:41] Coping with abuse aftermath and feelings of isolation.

[1:18:40] Debbie's experience being called a "corporate clown" and "she-devil."

[1:37:00] From lowest point to godmother: a transformative journey.

[1:37:38] The world-changing potential of brochures.

[1:43:14] The Design Matters podcast: origins and evolution over 12 years.

[1:46:46] Milton Glaser's impact on design and Debbie's life.

[1:52:16] The "10-Year Plan for a Remarkable Life" exercise.

[1:57:51] The nature of hard decisions.

[2:07:07] Recommended Design Matters episodes for design novices.

[2:07:55] Parting thoughts.

*

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Past 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.

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