How Success Breaks You and What to Do About It – Sherry Walling #151

Why Success Breaks Entrepreneurs and What to Do About It – Sherry Walling #151

 

Episode Summary

In this episode, Paul sits down with clinical psychologist and entrepreneur Dr. Sherry Walling to explore what really happens after the big business exit. They discuss why a financial windfall often triggers an identity crisis, how over-identifying with your company fuels loneliness and burnout, and why presence—not provision—is what our families truly want from us. Sherry also shares simple practices for emotional steadiness, including journaling, free-writing, and gratitude, along with her personal journey through grief, MDMA-assisted therapy, and ayahuasca. From stress habituation to heart-centred leadership and plant medicine, this conversation digs into what it means to stay human while building big things.

Key discussion points:

• Why exits often trigger depression, disillusionment, and relationship strain
• How fusing identity with your business sets you up for an existential crash
• The loneliness that comes with extreme success or high achievement
• Why many entrepreneurs unconsciously delegate the family to their partner
• Burnout as a repetitive-strain injury of the mind
• Habituation: how chronic stress becomes invisible
• Journaling, Morning Pages, and seeing yourself on paper
• The neuroscience behind gratitude and why it matters
• Building a company without martyrdom or 70-hour weeks
• The role of humility in leadership and delegation
• Sherry’s clinical work with trauma and the promise of MDMA-assisted therapy
• Her personal story of grief and how plant medicine supported her healing
• What ayahuasca actually is—and why it feels like medicine, not recreation

 

About the Guest — Dr. Sherry Walling

Dr. Sherry Walling is a clinical psychologist, author, and founder of ZenFounder, where she supports entrepreneurs through burnout, emotional resilience, trauma, and life transitions. She is also the author of The Entrepreneur’s Guide to Keeping Your Sht Together*, Exit Strategy (co-authored with her husband Rob Walling), and Touching Two Worlds, and integrates creative movement and aerial arts into her work. Learn more at zenfounder.com and touchingtwoworlds.com.

 

About the host:

Paul Ryan is an entrepreneur, 8 figure business owner, mentor, podcaster and creator of the 1-Hour CEO and Life Code Program. As a CEO, Paul has a depth of 'real life' experience of what it takes to be successful in business and life.

 Connect with the host:

Pauljryan.net 

https://www.linkedin.com/in/paul-ryan-9a98774/