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!

Bios of guests may be found at tim.blog/combo.

Listen to the episode on Apple Podcasts, Spotify, Overcast, Podcast Addict, Pocket Casts, Castbox, YouTube Music, Amazon Music, Audible, or on your favorite podcast platform.

This episode is brought to you by LinkedIn Jobs recruitment platform with 1B+ users, Eight Sleep’s Pod 4 Ultra sleeping solution for dynamic cooling and heating, and AG1 all-in-one nutritional supplement.

Transcript for the full Neil Gaiman episode | Transcript for the full Debbie Millman episode | Transcripts for all episodes

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What was your favorite quote or lesson from this episode? Please let me know in the comments.

SHOW NOTES

• [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.

SELECTED LINKS FROM THE EPISODE

Connect with Neil Gaiman:

Website | Twitter | Instagram | Facebook

Connect with Debbie Millman:

Website | Twitter | Instagram | Facebook | Design Matters Podcast

PEOPLE MENTIONED

The Tim Ferriss Show is one of the most popular podcasts in the world with more than one billion downloads. It has been selected for "Best of Apple Podcasts" three times, it is often the #1 interview podcast across all of Apple Podcasts, and it's been ranked #1 out of 400,000+ podcasts on many occasions. To listen to any of the past episodes for free, check out this page.