Episode
30

Bobbi Brown: How to Start Over When It Feels Impossible

with
Bobbi Brown
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Episode Description

Reinvention, identity loss, and personal growth aren’t just themes in Bobbi Brown’s story, they define it. Bobbi Brown, the legendary makeup artist and entrepreneur, described the moment everything she had built was suddenly gone. In an unexpected twist of midlife reinvention, she faced the loss of her identity, proving that even icons must confront the need for personal reinvention and bold career pivots.

For years, her name was everywhere, but behind the success, she was grieving the loss of who she thought she was and wondering how to reclaim her authentic self without it. Instead of staying stuck, Bobbi chose career reinvention. She found the courage to begin again, to take all the lessons from one life chapter and build something new on her own terms. Today, with Jones Road Beauty, she embodies women empowerment and shows us that reinventing yourself after 40 can be the most powerful act of all.

What you’ll learn

  • What it feels like to lose a piece of your identity and how to find your authentic self again
  • The courage it takes to start over when you feel like the rug’s been pulled out from under you
  • How rejection became Bobbi’s turning point for life reinvention
  • The mindset shifts that helped her rebuild with Jones Road Beauty
  • Why confidence is the foundation for navigating career pivots and moving forward stronger

If you’ve ever felt knocked down, questioned your worth, or wondered how to begin again, Bobbi’s story will show you that reinventing yourself isn’t just possible, it can be the most powerful chapter of your life.

Order Bobbi’s new book Still Bobbi: A Master Class in Leading an Authentic Life now!

Check out Jones Road Beauty for Bobbi’s no-make up make up look line of products

Timestamps

00:00 Introduction to Bobbi Brown

02:19 Stop asking, just start: Bobbi’s advice for new beginnings

03:17 Rethinking age and creating your own roadmap in midlife

04:43 Discovering her passion for makeup and inventing her own college major

06:07 The start of Bobbi’s entrepreneurial path

10:38 Selling her first company and life inside a corporate giant

15:13 The grief, rejection, and healing practices that helped her move forward

23:38 From Evolution_18 to Jones Road: building again from scratch

26:28 The story behind the “no makeup makeup” look

31:05 Why she finally wrote her memoir Still Bobbi, and who it’s for

33:56 Real beauty at every age and Bobbi’s commitment to diversity and authenticity

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guest appearing in this episode

Bobbi Brown

Bobbi Brown is a legendary makeup artist, founder of Bobbi Brown Cosmetics and Jones Road Beauty, and New York Times bestselling author of Still Bobbi. She joins Tamsen on The Tamsen Show to share how she navigated walking away from her namesake brand and built a second billion-dollar beauty company from scratch in midlife.

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medical disclaimer:

The information provided in this podcast is for educational and informational purposes only and is not intended as medical advice. Always consult with a qualified healthcare professional regarding any medical concerns or treatment options. The views expressed by guests are their own and do not necessarily reflect those of The Tamsen Show.