Design Matters with Debbie Millman

20th Anniversary Celebration: Iconic Musicians Special
Release Date: October 20, 2025

Episode Overview

In celebration of the 20th anniversary of Design Matters, host Debbie Millman assembles highlights from past interviews with renowned musicians who have graced the show. The episode reflects on the evolving relationship between creativity, music, and self-discovery, featuring conversations and performances with Khaki King, David Lee Roth, Lucy Wainwright Roche, Michael Stipe, and the Indigo Girls. Each guest shares personal stories about finding their artistic voice, overcoming obstacles, and sustaining a meaningful creative practice.

Key Discussion Points & Insights

1. Khaki King: Mastery, Individual Voice, and the Guitar as Truth

• Finding Identity as a Guitarist
  • Khaki discusses how she always knew she had talent, but emphasizes the importance of writing and finding her own voice rather than just showcasing technical skill.
  • Quote:
    “The playing is technical, like it can be taught, it can be practiced. The writing is very important. And ultimately developing my own voice as a writer in an instrumental context, that's the hardest thing to do.” (04:14)
• Rejecting Labels and the Myth of Mastery
  • Shares frustration with accolades like "guitar god" because they imply a ceiling: "There just is none... There is an infinite world of possibility on this instrument." (05:06)
  • Explains how forced comparisons (like "Bootsy Collins meets Van Halen") are reductive and unhelpful for creativity.
• The Challenge and Joy of Solo Touring
  • Describes solo acoustic tours as "like a martial arts challenge," and holding an audience's attention as both the hardest and most satisfying experience.
  • Quote:
    "I can't come up with anything more difficult and more satisfying." (06:55)
• Performance:
  • Khaki performs "Jessica," a song with a personal backstory, live in the studio. (08:14–11:34)

2. David Lee Roth: Identity, Survival, and the Power of Flaws

• Initial Realization and Performance as Lifeline
  • Roth humorously deflects the idea that he has "talent," insisting,
    “You're never completely there. You're always a work in progress. You're either going up the mountain or down the mountain.” (12:55)
• Origins of His Voice and Staying True
  • Shares formative story about singing for a teacher and learning what it meant to sing with meaning, referencing a Holocaust survivor, Salo Blumenthal.
  • Quote:
    “Mr. Roth, if you cannot find it in yourself to sing for those who did sing so you don't go up the chimneys.” (17:07)
• The Acceptance of Flaws in Art
  • Discusses how creative greatness comes from embracing imperfection:
    “My whole career was based on the flaw... therein lives the statement wabi-sabi. It's the flaw.” (20:31)

3. Lucy Wainwright Roche: Melancholy and Reinterpreting Joy

• Embracing Musical Sadness
  • Lucy speaks candidly about her love of sad songs and how even upbeat songs can strike her as melancholy.
  • Quote:
    “I really like sad music a lot… Most of the songs I love are really sad.” (21:37)
• Covering ‘Call Your Girlfriend’
  • Explains how she reimagined Robyn’s dance anthem as a “sad snoozer,” offering new emotional dimensions to familiar material.
  • Quote:
    “A lot of people think it's my song… I love that song because it's so unusual, like what she's saying.” (23:44)
• Performance:
  • Performs her acoustic, choral rendition of "Call Your Girlfriend" (25:32–29:33).

4. Michael Stipe: Vulnerability as Superpower & Creative Evolution

• The Power of Naïveté and Negation
  • Stipe recalls forming R.E.M. by purposely avoiding clichés, learning in public, and using negation as a compass for authenticity.
  • Quote:
    “We used a process of negation quite regularly to figure out what we did not want to be... I took it quite literal when they said anyone can do this. I was like, okay, that's me.” (34:24)
• Growth as an Artist
  • Confesses he didn’t know basic musical distinctions early on (e.g., difference between a bass and a guitar), sees public artistic evolution as both brave and awkward.
• Embracing Insecurity and Vulnerability
  • Credits finding "cold-ass bitch was a coat I put on to protect myself," learning that shedding artifice allows for truer connections and better art.
  • Quote:
    “I have those superpowers within my vulnerability and my insecurities. And I've actually employed those throughout my entire adult life.” (38:36)
  • Stipe also describes learning from Greta Thunberg to see personal differences as superpowers.

5. Indigo Girls (Amy Ray & Emily Saliers): Harmony, Identity, and Family

• First Encounter and Epiphany
  • Amy: Immediate sense of fate and creative soulmate connection on first singing harmonies with Emily.
    “I was like, this is it for me. You know, I found my path.” (43:49)
• Different Journeys, Shared Joy
  • Emily: For her, it was less an epiphany, more about the genuine fun and friendship:
    “What it was, was the most fun thing I was doing. And we became really good friends in high school... very soul connected.” (45:52–46:13)
• Navigating College, Self-Loathing & Family Tension
  • Amy details a difficult college experience in Nashville, battling depression, self-loathing, and internalized homophobia, compounded by her family’s struggle to accept three gay children.
  • Quote on Family:
    “They were destroyed in this way where ... Yet this one thing [having gay children] was so in opposition to their faith and everything they believed in and they just couldn't picture it. And their friends rejected them in the church. It was a long, very long road for them to get by...” (51:51)
  • Despite hardship, Amy celebrates her parents’ eventual acceptance and how support transformed their family.

Notable Quotes & Memorable Moments

• Khaki King on Mastery
  "There just is none [mastery]. There is an infinite world of possibility on this instrument." (05:06)

• David Lee Roth on "The Flaw"
  "My whole career was based on the flaw. ...therein lives the statement wabi-sabi. It's the flaw." (20:31)

• Lucy Wainwright Roche on Song Interpretation
  "A lot of people think it's my song… I love that song because it's so unusual, like what she's saying." (23:44)

• Michael Stipe on Becoming Oneself
  "We create. We become who we want to become, and then we create who we want to become and then we become them." (38:36)

• Amy Ray on Family Acceptance
  "They were afraid that they had done something wrong when they raised us because they were taught that this, what we are, was a perversion. So there was so much fear that it became anger." (51:51)

Timestamps for Key Segments

• Khaki King Interview & Performance: 03:59–11:34
• David Lee Roth Interview: 12:22–20:57
• Lucy Wainwright Roche Interview & Performance: 21:37–29:33
• Michael Stipe Interview: 34:24–43:06
• Indigo Girls Interview: 43:36–54:07

Episode Tone & Takeaways

The celebratory, deeply reflective tone highlights the wisdom of artistic veterans, the resilience of creative spirits, and the personal—and at times painful—journeys behind artistic mastery. Debbie Millman’s approach is intimate and respectful, encouraging openness about both vulnerability and achievement. Listeners are reminded that creativity is less about “making it” than constantly becoming, and that embracing flaws, uncertainty, and change is essential to both life and art.

For More:
Full interviews and archives at designmattersmedia.com.