Navigating Purpose and Fear in Entrepreneurship

Rick Eigenbrod is a deeply respected thinker in the post-exit world. A clinical psychologist and co-author of the classic Yale paper What’s Next: The Entrepreneur’s Epilogue, he’s spent years guiding founders through life after the exit as an executive coach. In this conversation, we get into why Rick believes a “death of who we used to be” and a subsequent "re-birth" are inevitable post-exit, and how resisting these changes only adds to the struggle. Rick generously shares the tools and exercises he’s found most effective in navigating this transformative process. We also explore the grip of dopamine addiction, the healing power of legitimizing post-success frustration, simple ways to reconnect with our natural curiosity and playfulness, and the bittersweet reality of leaving some people behind as we experience exponential personal growth. _____________________________________________________ TIME STAMPS: 00:00:00: Introduction 00:00:21: The paradox of success 00:00:43: Rick's background and contributions 00:01:04: Discussion on post-exit rebirth and struggles 00:01:12: Exploring dopamine addiction and post-success frustrations 00:02:30: Exploring the post-exit maze 00:02:45: Rick's background and experience with exited founders 00:04:47: Rick's critical event with Vistage group 00:06:09: The price and prize of money and freedom 00:07:52: Reflections on the dual meaning of success 00:08:53: Grappling with post-exit paradox 00:09:41: The "focusing illusion" and the arrival fallacy 00:11:12: The societal pressure to be happy post-exit 00:12:01: Support groups and legitimating experiences 00:13:08: Initial reactions and reflections on the post-exit reality 00:14:31: The societal issue of ignoring exited founders 00:15:33: The lack of support and self-blame post-exit 00:18:00: Escaping the blank sheet of paper 00:19:07: Dealing with loss of motivation 00:20:38: The challenge of striving without a company 00:22:21: Stories of loss of identity and success paradox 00:23:02: The impact on identity and structure post-exit 00:24:29: Avoiding the inclination to fill the void with the same elements 00:25:32: Closing the first business 00:26:18: Question of true desires and freedom paradox 00:27:19: Attempt to create a model from experiences 00:29:06: Journey from identity to meaning and structure 00:30:02: Revisiting personal development opportunities 00:33:16: Financial dangers post-exit 00:35:30: Paradox of money and its role 00:36:09: Evolution of the meaning of wealth 00:41:03: Refusal of the call and negative transfer of learning 00:44:10: Dopamine addiction as an obstacle 00:47:00: Fear of losing entrepreneurial identity 00:49:00: Navigating the journey of death and rebirth in personal growth 00:51:13: Leaving people behind during personal growth 00:52:29: Real journeys begin where fairy tales end 00:54:08: Redefining retirement and societal expectations 00:56:03: Advising young successful entrepreneurs 00:57:23: Identifying and addressing emotional struggles post-sale 00:58:46: Embracing a Mosaic Life 01:00:00: Communicating personal transitions to others 01:03:07: Returning to business after personal growth 01:05:00: Listening for truth, vitality, and fear in decisions 01:07:32: Distinguishing between legitimate fears and psychological barriers 01:09:08: Discernment of skill-related fears in new ventures 01:10:14: Transitioning from entrepreneur to investor 01:13:20: Rediscovering a sense of purpose post-exit 01:14:00: The search for meaning and what matters now 01:16:22: Two ways of knowing and going: Destination vs Direction 01:17:57: Understanding fulfillment and satisfaction 01:19:20: The importance of savoring moments 01:21:00: Stories about finding fulfillment 01:23:26: Legacy question 01:24:00: Discussion about dynamics of arrival 01:27:00: The role of intention in satisfaction