Design Matters with Debbie Millman

20th Anniversary Celebration with Acclaimed Directors
Guests: Brian Koppelman, Thomas Kail, Mike Mills, Sarah Polley, Siân Heder
Date: December 30, 2025

Overview

In this special 20th-anniversary episode of Design Matters, host Debbie Millman revisits some of her most insightful and heartfelt interviews with five acclaimed film and television directors: Brian Koppelman, Thomas Kail, Mike Mills, Sarah Polley, and Siân Heder. The episode explores the art and emotional depth of storytelling across different mediums, revealing how these visionary creators design both their projects and their personal lives through risk, vulnerability, collaboration, and a restless curiosity about the world.

Key Discussion Points & Insights

1. Brian Koppelman: Risk, Collaboration & Authenticity in Storytelling

• Impact of Early Cinema: Koppelman describes how films like She’s Gotta Have It, Raising Arizona, and Pulp Fiction shaped his understanding of how language—both visual and verbal—could transform film.

  “I realized there's this language in both a visual and a verbal language. And people can use language in film in this very specific way.” (04:17)

• On Collaboration: Shares his decades-long partnership with David Levine, emphasizing gratitude and process (06:05).
• Finding Story Inspiration: Discusses how personal dissatisfaction and a desire for authenticity (especially as a parent) led to taking risks and writing Rounders (06:45).
• Poker as Narrative Metaphor: Fascination with professional poker aligns with themes of risk-taking and reading others (08:44).
• Meditation & Self-Awareness: Practices transcendental meditation to manage anxiety, which relates to his ability to exist in a state of curiosity, essential for both life and poker (09:43, 10:20).
• Embracing Risk in Career: He structures life with his novelist wife, Amy, to allow for creative risks, avoiding toxicity and burnout by favoring projects that bring joy, not just commercial success:

  "If I'm not leading from a place of curiosity and fascination, I become sad and angry and miserable." (13:00)

2. Thomas Kail: Creative Community & Making Room for Others

• Early Days & Meeting Lin-Manuel Miranda: Shares anecdotes about first hearing about Miranda as a freshman, and the humor and rivalry that turned into lifelong collaboration (15:01, 15:51).
• Learning by Doing: Kail’s post-college apprenticeship at a theater company instilled humility and a relentless work ethic (16:08).
• Forming Back House Productions: Talks about building a theater company that forced him to learn every aspect of production (18:13).
• Inclusivity in Art: Describes how working in the Drama Bookshop’s basement taught him to support others’ success, rejecting a zero-sum approach to creativity (18:30).

  “It never occurred to me that someone else's success meant I couldn't achieve or there wasn't space for me.” (19:25)

• The Lin-Manuel Collaboration: Recounts the deep connection from their first meeting, and how synergy fuels creative success (24:31).

3. Mike Mills: Vulnerability, Simplicity, and the Universality of Loss

• Working from Confusion: Mills stresses the importance of exploring personal confusion and desperate questions to fuel charged, authentic filmmaking (25:35).
• Simplicity in Filmmaking: Inspired by Ozu’s fixed camera style, he uses visual restraint to let emotion and authenticity shine (28:57).

  “It's like a documentary photograph…there’s an openness, and you can kind of see the music or something.” (29:44)

• Depression & Creativity: Shares a personal family history of unspoken depression, turning vulnerability and shame into a source of artistic solace (30:26).
• Making ‘Beginners’: Explains the importance of recognizing loss as a shared experience—his father’s coming out and death as both uniquely personal and universally relatable (34:44).

  “I wanted to invoke the blues in a way—these are things that happen to all of us all the time, everywhere.” (34:44)

4. Sarah Polley: Multiplicity of Truths & Family Narratives

• Documentary ‘Stories We Tell’: Polley explores how family narratives and realities diverge, showing how everyone creates personal versions of truth from shared events (39:59).
• Uncovering Family Secrets: Describes discovering her biological father’s identity and the multiplicity of perspectives that family members held about the same event.
• Reframed Understanding of Truth:

  “I became less dogmatic about truth and more interested in what people need emotionally to survive.” (42:06)

• Listening and Empathy: Stresses the value of making space for others’ stories—don’t rush to correct but let others fill the silence (42:06).
• Impact on Self-Perception: Offers an anecdote about overhearing a family member express pride rather than the expected criticism, highlighting how we project our own narratives onto others, often incorrectly (43:20).
• Forgiveness and Compassion for Her Mother: After learning of her mother’s affair, Polley withholds judgment, appreciating the pressures women endure and the need for personal joy (46:44).

  “I just think it’s like, I can’t find it in my heart to judge her…She only lived till she was 53, and I’m so glad she had some fun while she was here.” (48:47)

5. Siân Heder: Representation & Empathy in Storytelling

• Writing for ‘Orange Is the New Black’: Recalls crafting the Emmy-nominated "Lesbian Request Denied," and the sense of responsibility in representing nuanced, complex characters, especially when tackling trans experiences (51:00).
  • Memorable moment: The comic mishap with an on-set pee rig for Uzo Aduba's character (51:14).
• Creating Authentic Characters: Describes the deep research and sensitivity involved in building Sophia's (Laverne Cox) character, pushing against the trope that minority or marginalized characters must be ‘pure’ (53:00).
• Participating in Cultural Change:

  “You get to feel like a cog in the wheels of change…you set the pebble rolling somehow at the top of the hill, and it picked up more pebbles and became an avalanche.” (55:35)

• Adapting ‘CODA’: Details the challenge and reward of telling a story about a deaf family, the unique cultural tension of being a CODA (child of deaf adults), and ensuring authenticity by hiring deaf collaborators and listening deeply (56:36).

  “The fact that [a film with a deaf family at its center] doesn’t exist in the world felt like a driving force to put it in the world.” (56:36)

• Collaborative Set Culture: Describes learning to adapt the film’s production to deaf culture, even down to set decoration—true collaboration and openness to being corrected as a mark of respect (58:00).

Notable Quotes & Memorable Moments

| Timestamp | Speaker | Quote | |-----------|---------|-------| | 04:17 | Brian Koppelman | "I realized there's this language in both a visual and a verbal language..." | | 05:55 | Debbie Millman | "The key to good collaboration is to be grateful for what the other person brings..." | | 13:00 | Brian Koppelman | "If I'm not leading from a place of curiosity and fascination, I become sad and angry and miserable..." | | 19:25 | Thomas Kail | "It never occurred to me that someone else's success meant I couldn't achieve or there wasn't space for me." | | 24:31 | Thomas Kail | "We were saying the same things, we were saying the same lyrics at the same time. It was just, where have you been?" | | 29:44 | Mike Mills | "It's like a documentary photograph… there's an openness, and you can kind of see the music or something." | | 34:44 | Mike Mills | "I wanted to invoke the blues in a way—these are things that happen to all of us all the time, everywhere." | | 42:06 | Sarah Polley | "I became less dogmatic about truth and more interested in what people need emotionally to survive." | | 48:47 | Sarah Polley | "She only lived till she was 53, and I’m so glad she had some fun while she was here." | | 51:14 | Siân Heder | "We built a P rig for Uzo and the first time she did it...the P rig, like, kind of just exploded in the gushiest way ever..." | | 55:35 | Siân Heder | “You get to feel like a cog in the wheels of change…you set the pebble rolling somehow at the top of the hill, and it picked up more pebbles and became an avalanche.” | | 56:36 | Siân Heder | “The fact that [a film with a deaf family at its center] doesn’t exist in the world felt like a driving force to put it in the world.” |

Timestamps for Key Segments

• Brian Koppelman: Writing, risk-taking, poker, and meditation — 02:42–14:19
• Thomas Kail: Early theater, collaboration with Lin-Manuel Miranda — 14:19–24:58
• Mike Mills: Drawing from confusion, family, and universality — 24:58–36:07
• Sarah Polley: Truth in documentary and family narrative — 39:10–49:15
• Siân Heder: Orange Is the New Black, authentic representation, CODA — 49:15–60:27

Tone & Style

Debbie Millman fosters conversations that are earnest, searching, and disarmingly honest. The directors are alternately playful and profound; there’s ample humor, vulnerability, and a focus on design as a vehicle for life.

Takeaways

• True creativity often emerges from vulnerability, confusion, and a willingness to question one’s own narratives.
• Collaboration, both in work and life, means making space for others' strengths, stories, and successes.
• Authenticity onscreen (and off) comes from attention to detail, lived experience, and a readiness to be challenged.
• Storytelling is both solitary and collective—a way to process the heartbreaks and joys of being human, and sometimes, to change the world.

For full-length interviews and more conversations with extraordinary creatives, visit Design Matters Media.