She built one of the first podcasts in the world. She turned down the CEO job after twenty years. And she wants you to ask yourself one question: if not now, when? In this episode of Truth Works, Jessica Neal and co-host Peter Clarke sit down with Debbie Millman, the founder and host of Design Matters, the longest-running design podcast in the world, now in its twentieth year. Over two decades, Debbie has interviewed more than 700 of the world's most creative people, written eight books, and shaped some of the biggest consumer brands on the planet, including Burger King, Häagen-Dazs, Star Wars, Tropicana and the No More campaign. She co-founded the world's first Masters in Branding program at the School of Visual Arts, is President Emeritus of AIGA, and in 2024 was named an Executive Fellow at Harvard Business School. This conversation goes way deeper than the résumé. Debbie talks about failing as an artist, writer, and designer before stumbling into branding by accident. She explains why she turned down the CEO offer at Sterling Brands. She shares what hundreds of interviews have taught her about confidence, insecurity, and reinvention. And she gets refreshingly clear-eyed about AI, and what it is quietly doing to the next generation's brains. TOPICS COVERED Failing as an artist, writer and designer before finding brandingBecoming the rainmaker at Interbrand and Sterling BrandsWhy she turned down the CEO offer after four months of deliberationHow Design Matters began in 2005 as a paid internet radio showWhat hundreds of interviews taught her about insecurity and legacyCareer advice for creatives and knowing your value propositionMarrying Roxane Gay and acquiring The Rumpus togetherWriting Love Letter to a GardenWhy AI should have a drinking ageThe one question she now asks herself every day: if not now, when?What makes this episode hit differently is not the résumé. I t is the reminder that even the most accomplished people on the planet built their lives the same way the rest of us have to, one brave decision at a time, often with no clue what was coming next. Debbie's story is proof that reinvention is always available, that confidence is built and never gifted, and that the best chapters of a life can absolutely come after sixty. If you take one thing from this conversation, let it be her question. Whatever you have been waiting to start, finish, or finally claim as yours, ask yourself honestly: if not now, when?
