Debbie talks to Chase Jarvis about his career as a photographer and entrepreneur.

Debbie talks to Bo Burnham about his film Eighth Grade, and the young star of that movie, Elsie Fisher.

Debbie talks to Scott Belsky about why creative conflict can lead to good decision making.

Novelist and memoirist Dani Shapiro shares her journey of self-discovery after uncovering a shocking family secret about her biological father. The podcast explores themes of identity, belonging, and the complexities of genealogy, paternity, and love. Shapiro reflects on navigating inherited trauma, gratitude, and the emotional turmoil of reconnecting with her biological father, revealing the impact on relationships and personal growth.

Jocelyn K. Glei talks to Debbie about how the internet can lead to burnout.

Josh Higgins talks to Debbie Millman about how to design software products that become popular with users.

Debbie talks to Alice Rawsthorn about the growing status of design.

Debbie talks to performance poet Sarah Kay about teaching people to write.

Debbie talks to illustrator Christoph Niemann about his singular career as an artistic superhero.

Debbie talks to singer-songwriter Shirley Manson about her career, her music, and the long road that got her where she is today.