People Who Are Making it Work
Call him Robert.
Seventy-four years old. Forty years in technology, the independent kind where you build your own client list, manage your own reputation, and live or die by the quality of your judgment and the strength of your relationships.
He was good at it. Very good. And when he decided he was done… he was done. No lingering ambivalence, no half-measures. He closed the business, handed off the clients he could, and stepped back.
For a while it was fine. More than fine, but Robert was starting to feel a bit disconnected from the world he had known.
Then a former client called with an offer.
It was a job, with good title, good money, interesting work. The kind of offer that’s easy to say yes to because it looks, on the surface, like exactly what he’d been missing.
He took it.
What he discovered in the following two years is something a surprising number of people discover when they trade a life they built for a structure someone else built.
The work was fine. The people were fine. But something was missing that he hadn’t thought to value until it was gone.
The thread was someone else’s to hold.
Every decision filtered through layers he hadn’t navigated in decades. Every instinct he’d spent forty years sharpening had to wait its turn in a process designed for people with less experience, not more.
He was valuable, they told him so regularly, but he was valuable on their terms, in their container, toward their goals and objectives.
After two years he left.
Not in frustration, more in recognition. He understood something about himself that the job had clarified, the way contrast clarifies things that comfort often obscures.
He wasn’t built for someone else’s structure anymore. Maybe he never had been.
Now Robert is rebuilding his own business. At seventy-four. Starting new conversations and reaching back to a network that turns out to have cooled faster than he expected.
He’s begun piecing together something that looks different from what he had before but runs on the same engine.
It’s slower than he’d like. Some days it’s frustrating in ways that early career frustration never quite was, because at seventy-four you’re aware of the clock in a way you simply aren’t at thirty-four.
But he’s the one holding the thread, and it turns out that matters to him more than he knew.
I’ve been thinking about Robert a lot lately.
Not because his story is unusual, versions of it are more common than most people know. But because of what it illustrates about the UnRetiring journey that the more linear text-book stories don’t.
The road to UnRetiring is rarely a straight line. There are attempts that don’t work out, detours that teach something, moments of genuine doubt about whether the effort is worth it.
What separates the people who find their way from the people who don’t isn’t the absence of those moments. It’s what they do when the version they tried doesn’t quite fit.
Robert tried the obvious thing. It didn’t fit. He learned something from it that he couldn’t have learned any other way. Now he’s trying something truer to who he actually is.
That’s not failure. That’s the process
I’d love to hear your version of Robert’s story, or something that looks different but carries the same essential truth.
Real stories from real people who are navigating their own UnRetirement are worth more than any guidelines I may come up with.
Join us on the journey.