Jen Gottlieb: How She Built Unshakeable Confidence

Jen Gottlieb is an entrepreneur, bestselling author, international speaker and former performer who has built a career around communication, visibility and being seen.

But this conversation goes far beyond how to look confident on a stage.

Jen and I talk about what it actually takes to trust yourself, allow yourself to be seen before you feel ready, practise publicly without needing everyone’s approval, and navigate the line between being vulnerable and sharing parts of yourself that still need time to heal.

In this episode:

The daily practice that became her “confidence boot camp”

Why being seen before you’re ready can accelerate your growth

What watching Jerry Seinfeld practise imperfectly taught her about becoming great

How to know what parts of your story are actually ready to be shared

And underneath all of it is one of Jen’s simplest ideas about confidence: every promise you keep to yourself becomes evidence that you can trust yourself.

If you’ve been waiting until you feel confident, polished or completely ready before you put yourself out there, this conversation will remind you that confidence isn’t something you have to wait for — it’s something you can build.

🎟️ JOIN JEN + ME AT FFFCON 2026 IN BOSTON

Jen and I will both be at FFFCon 2026, September 25–26 in Boston.