131. Confidence Was Never the Problem with Jess Weiner

What if confidence was never something women lacked; but something that was interrupted?In this conversation, I sit down with Jess Weiner - cultural expert, author of A Very Hungry Girl, and longtime advisor to brands like Dove and Barbie - to unpack the deeper story behind how women learn to see themselves, lead, and show up in the world.We go beyond surface-level “confidence” talk and get into the real work:- how social conditioning shapes women’s relationship to authority- why self-monitoring becomes second nature- and what it actually costs women—especially in leadership and high-stakes environments.This episode explores:The early conditioning that teaches girls to prioritize likability over self-trustThe hidden toll of constant self-editing and performanceWhy confidence isn’t missing—it’s been disruptedHow body image, identity, and leadership are more connected than we admitWhat it really looks like to unlearn these patterns as an adultThis isn’t about fixing women.It’s about questioning the systems that taught them to hesitate in the first place.If you’ve ever found yourself second-guessing what you already know, softening your voice in the moment it matters, or feeling the pressure to be both exceptional and acceptable—this conversation will hit.