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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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Our guest this week is Betsy Pepine, author of Breaking Boxes: Dismantling the Metaphorical Boxes that Bind Us, to explore the power of failure, reinvention, and resilience. Mentored by icons like Barbara Corcoran, Dave Ramsey, and Glenn Beck, Betsy shares how embracing failure and fear helped her rebuild her life and career, and how you can do the same.
If you’ve ever felt stuck in a box that no longer serves you, this episode will inspire you to break free, redefine success, and move boldly toward your purpose.
CHAPTERS
00:00 – Introduction: Mentored by Barbara Corcoran & Dave Ramsey
01:00 – Betsy’s Journey from Pharma to Real Estate
02:30 – Learning to Pivot After Setbacks
04:00 – How Mentorship Changed Her Career
05:15 – Lessons from Barbara Corcoran on Reinvention
06:45 – Ageism and Redefining Success at Any Age
07:30 – Finding the Right Mentor When You Don’t Have Connections
09:00 – Overcoming Fear and Self-Doubt
11:00 – Why Failure Isn’t Final: Lessons in Resilience
13:00 – Managing Fear of Financial Insecurity
15:00 – Redefining Failure and the Power of Perspective
16:00 – The Value of Journaling and Self-Awareness
17:30 – Breaking Out of Boxes That No Longer Serve You
19:00 – Betsy’s Toolkit: How to Identify and Dismantle Your Boxes
20:00 – Closing Thoughts and Where to Find Betsy’s Book
KEY TAKEAWAYS
– Failure is a stepping stone, not an ending.
– Mentorship can accelerate personal and professional growth.
– Fear often keeps us boxed in—breakthroughs start when you face it.
– It’s never too late to redefine success or start over.
– Journaling and self-reflection build clarity and confidence.
– Every setback prepares you for your next success.
Guest Links:
Book: Breaking Boxes – http://bit.ly/4389e3C
Website & Toolkit: betsypepine.com
Follow Betsy: @BetsyPepine
Host:
Janice Becker – Founder & CEO of Media Rebel
Connect with us!
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📸 Instagram: @mediarebeldigital
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💼 LinkedIn: https://www.linkedin.com/in/janicembecker/
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