Reclaiming Yourself After Years of Overgiving with Wendy Perrotti

The Real Reason You Keep Saying Yes When You Mean No - And What to Do About It

 

Many women spend decades being the reliable one — the helper, the fixer, the one who always says yes. Somewhere along the way, it can start to feel exhausting… and a little confusing.

In this episode of Late Bloomer Living, I’m joined by returning guest Wendy Perrotti, a master-level certified coach, speaker, and author who helps women over 50 create what’s next in their lives. Together, we explore why people pleasing isn’t a personality flaw — it’s a coping strategy shaped by culture, values, and a desire to feel safe and needed.

 

We talk about:

• Why overgiving often feels so hard to let go of
  
• How thought patterns keep people-pleasing in place
  
• What healthy boundaries actually look like (and why they don’t have to feel harsh)
  
• Why midlife is such a powerful moment for reclaiming yourself
• How play and experimentation can gently guide reinvention

Wendy also shares the story behind her new book, Keep the Tomato — a grown-up picture book for people pleasers — and how learning to “keep a few tomatoes for yourself” can change everything.

If you’ve been feeling tired of always being the one who gives, this conversation offers clarity, compassion, and permission to begin choosing yourself again.