The first was at 47, during a near-death experience that cracked open my sense of time and identity. The second is now, as I face a metastasizing cancer that has a way of stripping away anything that isn’t essential.
Both moments have asked me the same question, just with different urgency:
What actually matters—and what am I willing to let go of?
For most of my career, I’ve focused on success. Building, scaling, proving. I did that in spades with Joie de Vivre, the boutique hotel company I created at 26. I was an admiration addict based upon being the founder and CEO of a much-admired company for two-dozen years.
At MEA, this desire for success translated into creating something meaningful in the world—something that helps people navigate midlife with purpose and curiosity. But success, if we’re honest, often comes with a shadow: control.
You build it. You protect it. You hold it tightly.
Succession asks something entirely different (thanks to Lanny Vincent, a recent MEA grad, for the title of today’s post).
It asks for trust.
One of the phrases I’ve been sitting with lately is this: “My painful life lessons are the raw material for my future wisdom.”
It’s a comforting thought, but also a challenging one. Because wisdom isn’t just something you have—it’s something you practice. And right now, my practice is learning how to step back without stepping away. I was never able to do that at Joie de Vivre because I hadn’t created a succession plan.
I’ve learned my lesson. Today, this means allowing our talented leadership team—especially Derek, our CEO—to run the business with more latitude than I would have been comfortable with in the past. It means resisting the urge to weigh in on every decision, to shape every outcome. It means trusting that what we’ve built is strong enough to evolve without my constant hand on the wheel.
I couldn’t have done this in 2008 when I was running my boutique hotel company. Back then, my identity was too tightly fused with the business. Letting go would have felt like disappearing.
Now, it feels like something else entirely.
It feels like making space.
Succession isn’t about fading into irrelevance. It’s about transferring relevance. It’s about recognizing that the true measure of what you’ve built isn’t how long you can hold onto it, but how well it lives beyond you. Psychologist Erik Erikson suggested this mantra for later life: “I am what survives me.” There’s meant to be a humility in that (not an ego-driven legacy). And, surprisingly, a kind of relief.
Because when you stop trying to control everything, you start to see more clearly what only you can do—and what others can do just as well, or better.
So here I am, somewhere between success and succession. Still engaged, still caring deeply, but also learning to loosen my grip.
Not because I have to.
But because, finally, I can.
-Chip