Stop Waiting to Feel Ready | Debbie Millman on Courage, Confidence, and Writing

Debbie Millman explains why confidence is overrated and why courage is the real starting point for creative work.

In this episode, Debbie shares how confidence is built through repetition, why writer’s block often signals resistance rather than incapacity, and why the only creative failure that doesn’t heal is regret.

They explore procrastination, rejection, creative identity, and what it really means to work like a professional, even when the work feels uncomfortable.

This conversation is essential listening for anyone writing a book, building a body of work, or trying to move past fear and hesitation.

You’ll learn:

• The difference between courage and confidence

• Why repetition builds creative trust

• How professionals keep working without inspiration

• Why regret is harder to metabolize than failure

• How to design a sustainable creative practice