20th Anniversary Celebration with acclaimed directors Brian Koppelman, Thomas Kail, Mike Mills, Sarah Polley, and Siân Heder
Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.
Podcast Summary
In celebration of Design Matters' 20th anniversary, Debbie Millman revisits conversations with five acclaimed directors—Brian Koppelman, Thomas Kail, Mike Mills, Sarah Polley, and Siân Heder—exploring their creative processes, personal stories, and approaches to directing. (03:24) The episode examines how these directors serve as central collaborators, guiding creative teams from vision to execution while navigating the unique challenges of their respective mediums.
- Key theme: Directors as central collaborative forces who shape stories through personal vulnerability, authentic observation, and deep listening while managing the complex intersection of creative vision and industry pressures.
Speakers
Debbie Millman
Host and founder of Design Matters, the world's first podcast about design and one of the longest-running podcasts on the internet. She is also the founder of the Masters in Branding program at the School of Visual Arts in New York City, the first and longest-running branding program in the world.
Brian Koppelman
Multi-talented creator who has produced albums, written and directed films, and created television shows. He was the showrunner for the TV series Billions, which he also co-created, and co-wrote the acclaimed gambling film Rounders with his longtime writing partner David Levine.
Thomas Kail
Multi-award-winning director of plays and television shows who won a Tony Award in 2016 for his direction of the musical Hamilton. He previously worked as a personal assistant to Tony, Grammy, and Emmy Award-winning performer Audra McDonald and co-founded the theater company Backhouse Productions.
Mike Mills
Filmmaker known for his introspective and personal approach to storytelling in films like Thumbsucker, Beginners, and Twentieth Century Women. His work often explores themes of family relationships, depression, and the complexity of human connection through deeply observed, autobiographical narratives.
Sarah Polley
Former child and adult actor turned acclaimed director whose films include Away From Her and the Oscar-winning Women Talking. She directed the remarkable 2012 documentary Stories We Tell, which challenged conventional notions of narrative truth through exploring her own family's secrets.
Siân Heder
Director of the Oscar-winning film CODA, for which she won the Academy Award for Best Adapted Screenplay in 2022. She previously wrote for the groundbreaking Netflix series Orange is the New Black from 2013-2016, where she crafted memorable episodes featuring transgender and other marginalized characters.
Key Takeaways
Embrace Creative Risk Through Financial Discipline
Brian Koppelman reveals a crucial strategy for maintaining creative freedom: living below your means during profitable periods to fund passion projects during leaner times. (12:12) When he made money as a Hollywood screenwriter, he and his wife Amy consciously avoided lifestyle inflation, which later allowed them to take risks on independent films like Solitary Man. This approach enabled him to turn down Hollywood jobs he didn't want to take and pursue projects that aligned with his creative vision. The key insight is that true creative freedom requires financial discipline and long-term planning, allowing artists to make decisions based on artistic merit rather than immediate financial pressure.
Listen Without Agenda to Discover Truth
Sarah Polley's documentary-making process revealed a powerful approach to understanding others. (43:18) She learned from another documentary filmmaker to resist jumping in with the next question when someone finishes answering, as people often fill silence with more potent, unintentional revelations. This technique of patient listening without imposing your own narrative allowed her to discover family members had remained strangers despite years of interaction. The practical application extends beyond filmmaking—by listening completely and leaving space for others to fully express themselves, we often discover our assumptions about people are wrong and gain genuine understanding.
Transform Personal Confusion Into Creative Material
Mike Mills articulates why confusion is essential creative fuel: questions that are "gnawing at you and kinda tearing you apart on some level" make great film material because they maintain electric energy throughout the creative process. (25:50) Rather than working from comfortable, known perspectives, Mills seeks out his own areas of desperate need to understand or heal. This approach ensures the work remains alive and urgent rather than academic or detached. The strategy applies beyond filmmaking—identifying your deepest questions and uncertainties provides raw material for any creative endeavor, maintaining authentic engagement with your work.
Create Collaborative Space for Others' Success
Thomas Kail learned early in his career that other people's success doesn't diminish your own opportunities—a lesson crystallized when he quoted Hamilton's line about "the world was wide enough for both Hamilton and me." (20:27) Working in the basement theater of the Drama Bookshop, he discovered that welcoming others to make things he could never create enriched the entire creative ecosystem. This mindset shift from scarcity to abundance thinking enabled him to become a better collaborator and ultimately led to his work on Hamilton. The practical application involves actively supporting others' creative projects and recognizing that fostering others' success creates more opportunities for everyone.
Research Deeply When Writing Outside Your Experience
Siân Heder's approach to writing transgender and deaf characters demonstrates the importance of extensive research and collaboration when working outside your lived experience. (53:47) For Orange is the New Black, she attended trans support groups and interviewed numerous trans women, feeling "huge responsibility to get it right." For CODA, she surrounded herself with deaf collaborators both in front of and behind the camera, learning everything from how deaf families arrange furniture to how they structure their living spaces. This method of pure listening and acknowledging what you don't know, combined with building teams of authentic collaborators, ensures authentic representation while avoiding harmful stereotypes.
Statistics & Facts
- Netflix wasn't established as a streaming platform when Orange is the New Black began production—Siân Heder recalls getting the job and asking "Is this like an Internet show?" because streaming wasn't yet a thing, with only House of Cards as a reference point. (52:23)
- Most deaf people have hearing children, and most deaf people are born to hearing parents, creating a unique cultural divide where CODAs (children of deaf adults) often grow up more embedded in deaf culture than many deaf people themselves. (57:38)
- Thomas Kail worked as an assistant stage manager for only $84 per week after taxes ($100 gross) at the American Stage Company in Teaneck, New Jersey, living in windowless basement apartments while learning theater production. (16:47)
