

Surprising First Questions
Oct 6, 2025
In a special anniversary compilation, various past guests share their quirky answers to Debbie Millman's signature first questions. Eric Spiekermann discusses a climber’s harness that recalls childhood treehouses, while Roman Mars recalls attending college at 15. Jessica Hische humorously explains her cat’s name change to Olivia Benson. Other guests like Chip Kidd, Isaac Mizrahi, and Roxane Gay offer amusing and insightful anecdotes about life, creativity, and personal quirks, making this reflection on a two-decade tradition both nostalgic and entertaining.
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The Power Of A Playful First Question
- Debbie Millman explains she researches guests deeply and begins interviews with playful, personal first questions.
- She uses these to signal preparation, relax guests, and prompt candid conversation.
Harnessed For A Home Library
- Eric Spiekermann describes using a harness and remote to access books on very high shelves in his home library.
- He says being suspended midair feels like a tree house and leads to unexpected two-hour reading sessions.
Early College And Maize Obsession
- Roman Mars confirms he started college at 15 and later found genetics through plant biology at Oberlin.
- Discovering transposable elements in maize hooked him and shaped his scientific path.