I recently had the privilege of sitting down with Dr. Rick Eigenbrod on The Wealth and Purpose Podcast. Rick is the author of What Happens When You Get What You Want and co-author of a Yale case study titled What’s Next? The Entrepreneur’s Epilogue and the Paradox of Success. He has spent years studying what actually happens after success. Not the theory, but the lived reality of people who worked incredibly hard, reached the finish line, and found themselves surprised by what was waiting on the other side.
What struck me most in our conversation wasn’t a framework or a formula. It was this uncomfortable truth: most of us spend decades chasing a finish line, and almost none of us are prepared for what happens when we cross it.
The Fantasy We All Carry
Rick opened our conversation with a story about a man who had sold his company, walked away with significant wealth, and found himself deeply struggling. What was remarkable wasn’t the struggle itself. It was that no one around him could understand it. His peer group had moved on. His support network had disappeared. And the cultural narrative around him offered only one response: you got what you wanted, so what’s the problem?
This is what Rick calls the focusing illusion. When we picture the life we are working toward, we naturally focus on everything that will be gained. The freedom, the flexibility, the reward for all those years of sacrifice. What the picture leaves out is just as powerful, and far more consequential. The loss of daily structure. The relationships that quietly fade. The sense of identity that was built around something that no longer exists. The attraction of that picture comes not just from what we see, but from what it leaves out.
Rick referenced Stephen Sondheim’s musical Into the Woods, which takes classic fairy tales and plays them all the way to their happily ever after endings, but then asks the harder question. What happens in act two? Life, as Rick put it, is not a one-act play. And most of us have never been given a grown-up picture of what the reality looks like after the curtain falls on the first act.
What Money Can’t Replace
One of the most important insights from our conversation was this: when you achieve a significant goal, gain always comes with loss. And that loss tends to show up in three areas that most people never anticipate.
The first is structure. When you sell a business or step away from a career, you don’t just lose the work itself. You lose the rhythm of your days, the relationships built around that work, and the countless small routines that quietly gave your life shape. What time do you get up in the morning? Who do you talk to? What do you think about? These may seem like small things until they are gone all at once. As Rick described it, there is structure on top of structure on top of structure, and most of it is invisible until it disappears.
The second is meaning. Structure gives us something to strive toward, and striving gives us meaning. As Rick observed, satisfaction is the death of desire. We are wired for the pursuit, for the gap between where we are and where we want to be. When the goal is achieved, the meaning that lived inside that pursuit doesn’t automatically transfer somewhere new. You can’t achieve a goal and still have it.
The third is identity. For many high achievers, who they are and what they do have become deeply intertwined over decades of building. When the business is gone, so is a significant part of how they understood themselves. As Rick said, you can’t get what you want and remain exactly who you were. Part of you has to evolve, and that process takes real time. The Yale research Rick referenced suggests it typically takes about two years before people genuinely feel like they have found a new rhythm and sense of purpose. Two years is longer than most people expect, especially people who are used to solving problems quickly.
The Trap of Using Old Tools for New Problems
One of the things Rick said that stayed with me is that many people in this transition try to use old tools for new construction. The habits and mindsets that made them successful, the impatience, the laser focus, the instinct to measure everything by scope and scale and impact, become liabilities when the challenge in front of them is a blank sheet of paper. Hemingway once wrote that it takes more courage to face a blank sheet of paper than a bull in the ring. I think anyone who has navigated a major life transition knows exactly what he meant.
In business, a question is something you solve and move past. In this season of life, learning to sit with a question, to hold it rather than conquer it, is one of the most important skills you can develop. Rick calls this negative transfer of learning. The very things that got you here can work against you in getting to where you need to go next.
Stop Asking About Purpose. Start Asking What Matters.
When Rick works with people navigating this transition, he doesn’t start by asking what they want to do next. He starts with identity. Who are you now? Not who you were when you were building something. Who are you today? From there, he moves to a second question that I found particularly powerful. Not “what is your purpose?”, a question that can feel enormous and paralyzing for people who are used to concrete goals, but simply, “what matters to you now?”
That shift in language is more than semantic. The word mattering is accessible in a way that purpose often isn’t. It brings you into the present rather than asking you to architect a future you can’t yet see. And the answer to that question, once you find it, becomes the foundation for the third question: what structures, communities, projects, and relationships will allow you to express what matters most? Rather than identity and meaning being something you derive from structure, structure becomes a form of expression. That is a meaningful reversal for people who have spent their careers building things from the outside in.
Follow the Vitality
Perhaps the most practical piece of advice Rick shared was this: follow the vitality. As you move through this transition, pay attention to the moments when something lights you up, even slightly. Rick calls them inklings. Small glimmers of energy and excitement that point toward something true about who you are becoming. They have three qualities, he said: truth, vitality, and often a little fear attached.
The mistake many people make is that they find an inkling and immediately talk themselves out of it. They apply the same analytical rigor and impatience that served them so well in business, and they extinguish the spark before it has a chance to grow. The invitation is to do the opposite. Notice the glimmer. Move toward it. And then act on it, even before you are certain where it leads. In business, you don’t move until you know. In this season of life, moving is often how you come to know.
Rick also framed this entire journey in a way I found genuinely moving. He described it as the timeless hero’s journey. The leaving, the time in the wilderness facing unexpected challenges, and ultimately the return with something hard-won and worth sharing. The challenge is that most people don’t recognize they are on that journey. They are too busy feeling lost to see that the discomfort is actually the path.
What This Means for All of Us
Rick closed our conversation with a thought that has stayed with me since. He said that if you want to be unhappy, try to be happy. What we actually need to learn, and what takes real practice, is contentment. Fulfillment. The ability to recognize enough. That isn’t a passive or resigned way to live. It is, as Rick described it, a sustainable one. A life built not around the next milestone, but around what is already true and meaningful right now.
I think about this in the context of the families we work with every day. So many of them have built something remarkable. And the question of what comes next, financially and personally, is one of the most important questions they will ever face. Success is worth pursuing. But it is not the end of the story. It is, if we are willing to do the work, the beginning of a much more interesting one.
If you would like to listen to my full conversation with Dr. Rick Eigenbrod, you can find it on 🎧 [Apple Podcasts] | [Spotify] | [YouTube].
