Navigating Success and Vulnerability

In this episode, Debbie Millman shares how to begin—even when you feel unready, unqualified, or full of doubt. Debbie is a designer, author, educator, and host of the pioneering podcast Design Matters. She's also the chair of the Masters in Branding program at the School of Visual Arts and editorial director at Print magazine.

We talk about the creative risks Debbie took later in life, why fear and shame shaped her early path, and how she found fulfillment by making deeply personal work—without waiting for permission. From the grief of losing family to the joy of marrying at 57, this is a raw, powerful conversation about love, legacy, and the courage to start—even if you feel like a mess.

Some highlights we explore:

• The myth of readiness – Why waiting to feel “good enough” keeps us stuck in place.
• Failures that shaped the path – From rejected applications to bad jobs, how struggle created space for clarity.
• Creating without permission – Why Debbie’s most meaningful work began when she stopped waiting to be chosen.

Enjoy!