When I became president at 29, it happened over a weekend. On Friday, I was a regional sales rep. On Monday, I was running a $30 million company.
There was no five-year training plan. No executive onboarding. No carefully choreographed succession runway. Over the next 15 years, we grew the business from $30 million to more than $230 million and the team from 50 people to 450.
At the time, it looked reckless. Looking back, I’m convinced that what seemed like a disadvantage for me was actually an advantage for the company—one a slow, tidy transition could never have produced.
Reluctance to let go
We tend to romanticize gradual succession. We love the language of overlap, phased transitions, shadowing, and “wisely easing into change.” It sounds mature. It sounds strategic. But after watching dozens of founder-led and family-owned businesses navigate the same moment, I’ve started to suspect that slow succession often has less to do with the successor’s readiness and more to do with the current leader’s reluctance to let go.
Research backs this up: Founder-CEO transitions fail at two to three times the rate of non-founder ones. The problem isn’t usually capability on the other side of the handoff. It’s the handoff itself.
Of course the outgoing leader knows more. They’ve led longer. They’ve made more decisions. They’ve absorbed more scars. But every extra day they hold on tightly, every decision they continue to make, every conversation they continue to own, widens the gap between their knowledge and the successor’s eventual capability.
At some point, succession stops being about development and starts being about dependency.
And underneath that dependency, more often than not, is identity. For many founders and long-tenured leaders, the business stopped being just a business years ago. It became purpose, meaning, community, the place where they felt most alive, needed, and in control. So when it’s time to let go, the tension isn’t operational. It’s personal. Stepping away can feel less like a transition and more like a loss—not of a role, but of a self.
I’ve heard countless founders say of their successor, “They’re just not quite ready yet.” Maybe. But the question worth asking is the harder one: Are you sure they’re not ready to grab the baton? Or are you not ready to put it down?
Forged under pressure
Leadership readiness rarely develops in the passenger seat, and it never happens by accident. Most leaders are forged under pressure, not protected from it. Sometimes the current leader holds on not because the next generation lacks capability, but because the current leader cannot yet imagine a compelling future beyond the role they currently occupy. The organization built to create freedom slowly becomes a set of handcuffs to the present.
In founder-led and family-owned businesses especially, drawn-out transitions tend to create their own problems: politics, divided loyalties, organizational drift. When succession stretches indefinitely, the company gets stuck between two eras. The less of the baton the outgoing leader releases, the less there is for the next generation to grab. Ironically, the attempt to minimize disruption tends to prolong it.
One of the unexpected gifts of an overnight transition was that there was no time for internal campaigning. No factions formed. No endless speculation about what could have been. The organization simply had to move. And so did I.
Not fully ready
At 29, I wasn’t fully ready to be president. But if the company had waited until I felt ready, I’m not sure I ever would have been. Responsibility accelerates growth. So does necessity.
That kind of acceleration is uncomfortable, especially for the incoming leader. Overnight transitions expose insecurity quickly—there’s no time to curate the appearance of competence. You either grow into the role or you don’t. But pressure also produces humility, decisiveness, adaptability, and the willingness to lean on others, often faster than any prolonged succession model can.
Leadership transitions are rarely painless. But in many organizations, the pain isn’t caused by the change itself. It’s caused by the avoidance of a change that’s coming whether anyone wants it to or not.
So for founders, executives, family business leaders—and, frankly, for parents— there’s a question worth sitting with:
Why aren’t we letting go?
Is it because the next leader truly isn’t capable? Or is it because we’ve built our identity around being needed, and can no longer picture a future for ourselves where we’re not?
Every leader lets go eventually. The only real question is whether we do it on our terms, or wait until circumstances make the decision for us.