The Question the First Game Doesn't Ask
For a long time, the goal was simple: more.
More growth. More revenue. More opportunity. More optionality. The assumption—rarely stated, but always present—was that more is always better. More security. More freedom. More ability to live life on our own terms. And for a while, that assumption held. Building creates momentum. Progress compounds. Each step forward expands what feels possible.
The first game is designed to make "enough" hard to recognize. There is always another level. Another opportunity. Another reason to continue. Even when the original goals have been met, the momentum remains. And momentum, once established, is hard to interrupt voluntarily—especially when the environment around you is full of people who are still building, and the culture of entrepreneurship treats continuation as virtue and stopping as failure.
The question "Is this enough?" rarely gets asked inside the game. There are no natural pauses for it. The scoreboards don't display it. It takes something external—a diagnosis, a loss, a season of travel far from the familiar rhythms—to make it visible.
The Last School
We sold our three schools in 2021. Private equity had come looking during COVID, and after more than a decade of building, we were able to negotiate terms that made sense. The chapter was closed.
Six months later, we opened another one.
It was a location Shirley had wanted for years—the landlord hadn't been willing before, but the timing was finally right. The plan made sense: bring in a seasoned director, own it passively, and sell the school to her in a few years for a tidy profit. We both liked it.
What we didn't anticipate was the execution. When we tried to formalize the partnership, we couldn't reach agreement. The director backed out. We were left holding a lease and no one to run the school.
We built it. It opened a year later. We ran it for three years. And we sold it—four years after we thought the chapter was closed.
What We Traded
The school wasn't a disaster. We didn't lose money, and the tax treatment along the way was actually favorable. By financial measures, it was worthwhile.
But financial measures aren't the right ones here.
While we were running the school, Shirley faced a serious health challenge. It arrived during a period when we were already carrying more obligation than we had intended. Her recovery was successful—for which I am profoundly grateful. But it clarified something that had been easy to avoid thinking about: we had assumed, without quite saying it, that time, vitality, and optionality were more durable than they actually are. That we could take this risk, carry this obligation for a few years, and still have the same health and energy and freedom on the other side.
That assumption was wrong. Not catastrophically wrong—we are, by any measure, fortunate. But wrong in ways that only became clear in hindsight, when we could look back and see what the intervening years had cost.
Three years of strength. Three years of vitality. Three years of the kind of freedom we had worked for more than a decade to earn—spent running a school for money we didn't need to make.
In hindsight, if we had it to do over again, we would not have built that last school.
At some point before we signed that lease, we already had enough to live a rich, adventurous life—maybe not a luxury-maximized one, but a genuinely good one. What we traded, without fully realizing it, was time.
Why "Enough" Is Hard to See
I want to be careful here, because this story is easy to misread.
It isn't a cautionary tale about greed or poor judgment. Shirley's motivation was genuine. So was mine. We moved forward from a real place—a shared belief in the opportunity, and in each other's judgment. These are not bad instincts.
The harder insight is this: the habits and instincts of the first game don't expire automatically when the game ends. The drive to build, to help, to stay involved, to use your knowledge, skills and resources in service of something—these are the same instincts that built the schools in the first place. They're not flaws to be eliminated. They just belong to a different game than the one we were now supposed to be playing.
Recognizing "enough" is not a single moment of clarity. It tends to emerge gradually, often in hindsight, as tradeoffs become visible across a longer stretch of time. The challenge is that the signals are subtle, and the environment often reinforces continued building—there is status in it, recognition, a sense of forward movement. Stopping requires something different. Not ambition. Not discipline. Discernment.
The ability to recognize when the return no longer justifies the cost. And the willingness to act on that recognition, even when the culture around you doesn't reward it.
Enough as a Filter
Once "enough" is recognized—not as a number, but as a condition—it becomes practical.
It becomes a filter for decisions. Not just "what could this produce?" but "what would this require?" Time. Energy. Attention. Risk. Freedom. These costs are often less visible than financial outcomes, yet they shape lived experience more directly than almost anything else.
Decisions evaluated through that filter look different. The new opportunity that would require two years of serious involvement—is the upside worth two years of the freedom we have now? The commitment that seems manageable at the beginning but carries real obligation—what does it look like in year three, if circumstances change?
The question isn't whether to build or stay active or continue contributing. It's whether the specific thing in front of you is worth what it would actually cost—measured in the currency that matters most at this stage of life, which is not money.
We built one more school than we needed to.
The recognition that we already had enough—and what that means for how we evaluate what comes next—is one of the most useful things that experience taught us.
Even if the cost of learning it was higher than it needed to be.