Episode Details

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!

Sponsors:

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.)

Eight Sleep’s Pod 4 Ultra sleeping solution for dynamic cooling and heating: https://eightsleep.com/tim (save $350 on the Pod 4 Ultra)

LinkedIn Jobs recruitment platform with 1B+ users: https://linkedin.com/tim (post your job for free)

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