When Success Becomes Your Cage: The Journey to Breaking Free from Expectations - Betsy Pepine

Season #2

What if the life you built — the one that looks perfect on paper — feels like a prison behind the scenes?

In this deeply honest conversation on The Ownership Game, Gary Montalvo sits down with Betsy Pepine, a successful real estate entrepreneur and author, who shares her story of what happens when outward success clashes with inner fulfillment.

Betsy opens up about the moment she realized she was living inside “boxes” built by other people’s expectations — and the courageous journey she took to break free, rewrite her story, and define success on her own terms.

If you’ve ever found yourself chasing achievement but feeling empty, questioning the stories you’ve inherited, or wondering how to live a more authentic life — this episode of The Ownership Game is for you.

 

In this episode, we discuss:

  • The hidden cost of the hustle culture
  • How “boxes” keep us stuck in invisible cages
  • The fear of letting go of status, identity, or financial security
  • Practices for tuning in, asking better questions, and creating real freedom
  • How to redefine your relationship with success and failure
  • Why unlearning old programming is the key to authentic leadership

 

Chapters: 

00:00 Introduction: When the Hustle Becomes the Cage

02:30 Meet Betsy Pepine: Success on Paper, Disconnection Inside

06:00 The First Signs: Listening to the Body and Inner Voice

09:30 Tools for Uncovering the Truth: Therapy, Meditation & More

14:45 Defining and Spotting the “Boxes” You Live In

19:20 Social and Cultural Boxes: Gender, Money & Status

25:00 The Ego Death of Changing Careers and Identities

31:30 Framework: Identifying Your Boxes and Facing the Fears

36:50 Betsy’s Book and How It Can Help Others

40:10 Powerful Takeaways: Joy, Impact, and Authenticity

46:30 Closing Reflections: Remembering Who You Really Are

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Connect with Betsy:

Instagram: https://www.instagram.com/betsypepine/ 

Facebook: https://www.facebook.com/betsypepine

LinkedIn: https://www.linkedin.com/in/betsypepine/

Website: https://www.betsypepine.com/

YouTube: https://www.youtube.com/@BetsyPepine 

Tiktok: https://www.tiktok.com/@gainesvillerealtor 

 

Grab Betsy’s book Breaking Free from the Boxes: https://www.amazon.com/Breaking-Boxes-Dismantling-Metaphorical-That/dp/1636802842/ref=tmm_hrd_swatch_0?_encoding=UTF8&qid=&sr= 

Join Betsy’s new companion course coming soon!

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