Dare On with Jodi

Goodbye People-Pleasing — Boundaries That Create the Life You Want


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Text us 1 takeaway from this episode (don’t forget the episode #). We read every message—even if we can’t reply!🥺

Are you secretly exhausted from always saying “yes”? Do you find yourself doing things for everyone else, while your own dreams sit on the back burner?
 This week on Beyond Empty Nest, I’m talking with leadership coach and community builder Jessi Sheridan about the real cost of people pleasing—and how setting healthy boundaries can help you design a life you truly love.

Jessi’s story will inspire you to ask the big questions, get crystal clear on your values, and create a vision for your days that leaves you feeling fulfilled, not depleted. We cover:

  • Jessi’s journey from working with college women to leading a thriving women’s community
  • How a single "What impact do I want to make?" question changed her life
  • Why identifying your top values is the key to healthy boundaries
  • Practical ways to say “no” without guilt
  • How to recognize when you’re people pleasing—and what to do about it
  • The surprising link between boundaries and stronger relationships
  • Jessi’s dare for you: put yourself first every single day

This conversation is your permission slip to stop overcommitting, ditch the guilt, and start intentionally designing a life you love.

Resources & Links Mentioned in This Episode:

  • Connect with Jessi Sheridan → habitualleadership.com
  • Join the Dare On Membership Community → dareontowhatsnext.com/moms-who-double-dare
  • Free Resource: 5 Dares for Connection and Well-Being
  • Moms Who Dare Facebook Group → Join Here

The Dare On Retreat is a soulful fall reset for women ready to step out of the noise and reconnect with themselves—guided by Jodi Silverman and CJ Stasik in the peaceful Poconos. Spots are limited to just 16 women, so if your heart is saying this is for me, grab your spot HERE before it sells out.

DISCLAIMER: The commentary and opinions available on this podcast are for informational and entertainment purposes only and not for the purpose of providing medical, physical, or psychological advice. You should contact a trained medical professional before making any significant changes to your health and wellness routine and with respect to any particular issue or problem.

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Dare On with JodiBy Jodi Silverman

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