The Paradox of Success: Why Getting What You Want Isn’t Enough with Dr. Rick Eigenbrod (Ep. 15)

The Paradox of Success: Why Getting What You Want Isn’t Enough with Dr. Rick Eigenbrod (Ep. 15)

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In this episode of the Wealth & Purpose Podcast, Brady Fineske speaks with Dr. Rick Eigenbrod, author of What Happens When You Get What You Want and co-author of the Yale case study What’s Next? The Entrepreneur’s Epilogue and the Paradox of Success. Dr. Eigenbrod shares what actually happens after achieving significant success — not the theory, but the lived reality experienced by entrepreneurs, executives, and high achievers who reach the finish line only to find it isn’t what they imagined.

The conversation explores why so many successful people feel lost, adrift, and unprepared after selling a business or reaching a major life milestone, and what it takes to rediscover structure, meaning, and identity on the other side of success.

Dr. Eigenbrod emphasizes the importance of understanding who you are now, what truly matters to you, and how to follow the small signals of vitality that point toward a more fulfilling next chapter.

Key points from this episode:

  • Why achieving a significant goal can come with unexpected loss, and why so few people are prepared for it
  • How the disruption to structure, meaning, and identity creates the “paradox of success”
  • Why the tools that made you successful can actually work against you in this next phase of life
  • The focusing illusion — and why our picture of “happily ever after” leaves out everything that matters
  • Why “purpose” can feel overwhelming, and the simpler question to ask instead
  • How to follow the vitality — the small inklings that point toward your next chapter
  • Resources, programs, and books to help navigate life after the exit

Connect with TFO Wealth Partners: 

Learn More About Dr. Rick Eigenbrod:

About Our Guest, Dr. Rick Eigenbrod:: 

Dr. Rick Eigenbrod is an experienced Executive Coach, Organizational Development Consultant, and author of What Happens When You Get What You Want. His work centers on helping leaders and high achievers navigate growth, transition, and performance through innovative approaches to leadership development and change management. He is also co-author of the Yale case study What’s Next? The Entrepreneur’s Epilogue and the Paradox of Success.

He has led change management and performance projects for organizations including AT&T, Google, United HealthCare, and the Hewlett Foundation, and has served as a featured Resource Speaker for more than 500 Vistage groups nationwide, earning the distinction of USA Speaker of the Year for Vistage Canada.

Rick holds a Ph.D. in Clinical Psychology from Michigan State University, an M.A. from Auburn University, and a B.A. from Tulane University.

TFO Wealth Partners, LLC (“TFO”) is an SEC-registered investment advisor located in Maumee, OH. Brady Fineske is a Partner and investment adviser representative of TFO. Registration with the SEC does not imply a certain level of skill or training. The opinions expressed in this podcast are for general informational and educational purposes only, are subject to change at any time, and should not be construed as TFO’s or Mr. Fineske’s solicitation to effect, or attempt to effect, transactions in securities, or the rendering of personalized investment advice. 

All investments and strategies, including any described in this podcast, have the potential for profit or loss. Past performance does not guarantee future results.  Any index performance described in this broadcast does not reflect the deduction of transaction, management, or other fees that would decrease performance results. While the information presented in this podcast is believed to be factual and up to date, TFO or Mr. Fineske does not guarantee its accuracy, and it should not be regarded as a complete analysis of the subjects discussed. Listeners should not rely on the content of this podcast as the sole basis for their legal, tax, investment, financial planning or estate planning decisions and should always consult an attorney or tax professional or any other investment professional regarding what may be appropriate for their specific situations.


534aWP – 2026.05

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