286: How Jenna Dewan Built Unshakable Confidence (From Dancing With Janet Jackson to "Step Up")

Jenna Dewan is an actor, dancer, producer, and one of the most iconic performers of our generation, and she is joining Josie for a candid conversation about ambition, confidence, motherhood, and what it really takes to build a dream life. From dancing for Janet Jackson at just 18 to becoming a household name with "Step Up," Jenna has had a fascinating career but this conversation goes far beyond the glamorous highlight reel. She opens up about purpose, how she built confidence from a young age, what performing on the world’s biggest stages taught her about self-belief, and the powerful leadership lessons she learned from Janet Jackson. We also get into motherhood, evolving identity, navigating ambition as a woman, and how to stay grounded while moving through major life transitions.

If you’ve ever wondered how successful women actually build confidence—or needed a reminder to trust your own path—this episode is for you.

In this episode, we discuss:

What dancing for Janet Jackson taught her about confidence, leadership, and success
How to build self-belief before you have proof
Why perfection leaves you feeling small
The pressure women feel around ambition, parenting, and “doing it all”
Jenna’s perspective on motherhood, identity, and personal evolution
Why kindness and power can absolutely coexist

CHAPTERS:

0:52 - Introduction

2:40 - Rooted In Childhood

5:32 - Building Confidence From An Early Age

9:40 - Turning An Artistic Passion Into A Career

12:49 - Dancing With Janet Jackson At 18 Years Old

20:51 - From Professional Dancer To Professional Actor

32:46 - Balancing Motherhood And Career

36:04 - Setting The Best Example For Your Kids

42:29 - Why Wellness Matters

49:50 - Final Thoughts

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