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Surprising First Questions

Surprising First Questions

Update: 2025-10-06
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This special 20th-anniversary episode of Design Matters features Debbie Millman revisiting early, playful questions posed to a diverse group of guests. The episode highlights unique anecdotes from various creative professionals, including Eric Spiekerman's harness bookshelf, Roman Mars's early college aspirations in corn genetics, and Jessica Hische's cat named after a TV character. Illustrator Sophie Blackall discusses her fondness for drawing animals in clothes, while book designer Chip Kidd recounts an anecdote about his broken glasses at a TED talk. Magazine editor Susan Sontag shares a story about resigning from a job, and Ben Schott reveals his past as a funk band drummer. Fashion designer Isaac Mizrahi explores the nature of style, and food writer Julia Turshen shares her lifelong passion for cooking. Cartoonist Roz Chast recounts a significant family story, and graphic novelist Alison Bechdel discusses lifelong passions. Cindy Gallop describes her distinctive apartment designs, and director Thomas Kail reflects on musical influences. Writer Roxane Gay delves into the performance of likability. The episode concludes with Debbie Millman reflecting on the podcast's milestone and previewing future content.

Outlines

00:00:00
Design Matters 20th Anniversary: Quirky Guest Stories

Debbie Millman celebrates 20 years of Design Matters by revisiting early, playful questions posed to guests, showcasing surprising and personal answers. This includes Eric Spiekerman's unique bookshelf, Roman Mars's early college start, Jessica Hische's cat's name origin, Sophie Blackall's fondness for drawing animals in clothes, and Chip Kidd's broken glasses at a TED talk.

00:17:03
Career Reflections and Creative Insights

Guests share diverse career experiences and insights. Susan Sontag discusses a peculiar early job offer, Ben Schott reveals his past as a funk band drummer, and Isaac Mizrahi explores the nuances of true style. Julia Turshen shares her deep-rooted passion for food, while Roz Chast recounts a formative family story.

00:32:56
Evolving Passions and Design Philosophy

The episode continues with Alison Bechdel discussing lifelong passions inspired by a Mad Magazine cartoon, Cindy Gallop detailing her unique apartment designs, and Thomas Kail reflecting on musical influences on his storytelling. Roxane Gay offers her perspective on the performance of likability, and Debbie Millman concludes by reflecting on the podcast's 20-year journey and future plans.

Keywords

Design Matters Podcast


A podcast hosted by Debbie Millman, featuring interviews with influential figures in design, art, and culture, exploring their creative processes and life stories. Celebrates 20 years of insightful conversations.

Eric Spiekerman


A typographer who discusses his unique, harness-operated bookshelf system designed for accessing books in a multi-level apartment.

Roman Mars


Host of 99% Invisible, who reveals his early start in college at 15, driven by a passion for learning and science, specifically corn genetics.

Jessica Hische


Designer who shares the story behind her cat's name, Olivia Benson, inspired by her love for Law & Order SVU.

Sophie Blackall


Illustrator who admits to a fondness for drawing animals in clothes, comparing it to dressing up children.

Chip Kidd


Legendary book designer who recounts the story of his broken glasses at a TED talk and how he improvised.

Susan Sontag


Magazine editor who discusses accepting and then immediately resigning from a job writing letters for a porn magazine during a recession.

Ben Schott


Author of Schott's Miscellanies, who reveals his past as a drummer in a funk band.

Isaac Mizrahi


Fashion designer who explores the concept of stylishness, suggesting true style emerges during "slovenly" moments.

Julia Turshen


Food writer who shares her lifelong passion for food, from early cooking classes to her signature fruit salad technique.

Q&A

  • What is the unique feature of Eric Spiekerman's bookshelf?

    Eric Spiekerman uses a harness system to access books on a very high bookshelf in his apartment, allowing him to ascend and descend like a climber.

  • Why did Roman Mars go to college at 15?

    Roman Mars was eager to be in college and loved learning. He researched colleges from a young age, believing it was where he would be happiest, and pursued science, eventually focusing on genetics.

  • What is the significance of the name Olivia Benson for Jessica Hische's cat?

    Jessica Hische, a fan of Law & Order SVU, named her cat Olivia Benson after the show's lead character, admiring her strength and style.

  • What is Sophie Blackall's artistic quirk regarding animals?

    Sophie Blackall enjoys drawing animals but often feels compelled to put clothes on them, believing they look better dressed, though she admits it might not be in their best interest.

  • How did Chip Kidd end up with half-framed glasses at his TED talk?

    Chip Kidd's glasses, his signature item, were broken by a loved one two weeks before his TED talk. Unable to fix them, he wore them as is, finding they still stayed on his face.

  • What was Susan Sontag's first job offer after college, and why did she decline it?

    Susan Sontag accepted a job writing letters for a porn magazine but resigned before starting because she felt the job was based on a lie and she didn't want to do that kind of work.

  • What is Ben Schott's surprising past musical endeavor?

    Ben Schott played drums in a funk band. He recently had the opportunity to play again at an event, describing his drumming as "average white drumming."

  • How does Isaac Mizrahi define true stylishness?

    Isaac Mizrahi believes true stylishness is demonstrated not in perfectly put-together moments, but in the impulse to add stylish touches, like lipstick or slippers, during relaxed, "slovenly" times.

  • What is Julia Turshen's earliest memory of her passion for food?

    Julia Turshen recalls giving a cooking class on how to make fruit salad to her great-grandmother and her friends when she was only five or six years old.

  • What is the story behind Roz Chast's family's delayed decision to have another child?

    Roz Chast's parents waited nearly 15 years to have her after her mother suffered a miscarriage while trying to change a light bulb, a traumatic event that deeply affected them.

Show Notes

In celebration of 20 years of Design Matters, Debbie Millman revisits one of the show’s most endearing traditions—the very first question. For years, she’s opened each conversation with a playful, deeply researched inquiry: something personal, unexpected, and revealing. In this special anniversary episode, listeners will hear some of Debbie’s favorite first questions and the illuminating answers they inspired.
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Surprising First Questions

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