The Entrepreneur’s Guide to Keeping Your Sh*t Together: With Dr. Sherry Walling

My Guest


This week, I was thrilled to welcome Dr. Sherry Walling to the podcast. Sherry is a clinical psychologist, speaker, podcaster, and best-selling author. She is also a founder and entrepreneur herself, starting a company called ZenFounder, which aims to help entrepreneurs and CEOs navigate issues of transition, rapid growth, loss, and any manner of complex human experience. She is also the host of the ZenFounder podcast, which has been called a “must listen” by both Forbes and Entrepreneur Magazine and has been downloaded more than 1M+ times.

Sherry first came onto my radar when she published her first book, the aptly named The Entrepreneur’s Guide to Keeping Your Sh*t Together, which discusses many of the topics that we’ve explored over the years in this podcast related to managing your psychology as an entrepreneur and CEO.

I decided to invite Sherry onto the podcast upon learning of her most recent book, titled Exit Strategy: The Entrepreneur’s Guide to Selling Your Business without Regret, which goes beyond purely commercial considerations, and explores the largely unexplored personal considerations specific to the largest transaction of most entrepreneurs’ lives.

Sherry is graduate of the University of California, Davis and Fuller School of Psychology. She has a PhD in clinical psychology and master’s degrees in both psychology and theology. She completed research fellowships at Yale University School of Medicine and the National Center for PTSD in Boston.

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Episode Summary with Timestamps

  • 00:00 Navigating Entrepreneurial Ambition

  • 04:46 Understanding Anxiety in Entrepreneurship

  • 07:37 Recognizing and Addressing Burnout

  • 10:30 The Fear of Success and Self-Sabotage

  • 13:29 Preparing for Business Exit Strategies

  • 16:25 The Personal Impact of Selling a Business

  • 31:56 Navigating Emotional Reactions in Business Transactions

  • 34:52 Post-Exit Advice: Spending and Time Off

  • 38:25 Communicating Exits: Balancing Transparency and Employee Concerns

  • 43:25 Identity and Transition: The Entrepreneur’s Journey

  • 48:08 Generational Perspectives on Exiting Businesses

  • 51:41 The Importance of Sleep and Self-Care for Entrepreneurs

  • 53:16 Community and Support: Finding Your Tribe Post-Exit

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Thanks to our Sponsors

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