Nobody really asks me what I do anymore. What they ask, instead, is whether I’m retired.
I usually say yes. I say I’m retired from real estate, and I leave it there, without going into any detail. The truth is, I enjoy saying it. Real estate had stopped satisfying me long before I stepped away from it, and there’s a real liberation in no longer having to describe myself by a job that no longer fit. When people ask if I’m retired, what runs through my mind isn’t nostalgia. It’s something closer to why didn’t I do this sooner?
But here’s the thing I rarely say out loud: the word itself doesn’t actually describe what happened to me. I’m not retired, not in the way most people mean it. I never had the thing retirement is supposed to be built on top of.
What Retirement Was Supposed to Mean
To me, retirement has always meant something specific: you complete a career, you accumulate enough wealth along the way, and at some agreed-upon point, you no longer need regular income to maintain a comfortable life. That’s the version of retirement built into our culture — the gold watch, the pension, the fixed date after which the paycheck simply continues to arrive, generated by decades of saved and invested labor.
I never had that. I don’t have it now. And when I really think it through, I don’t believe I’ll ever reach that point in my life.
I’ve spent nearly all of my working years running small businesses of my own — in real estate, and now building The Encore Project. No employer ever cut me a paycheck I could count on landing every other Friday. No pension has ever been waiting for me at the end of a service requirement. I chose that path, and mostly I don’t regret it. But it does mean the word “retirement,” as most people use it, was never really built to describe someone like me.
The word ‘retirement,’ as most people use it, was never really built to describe someone like me.
My Father's Version
I come by this honestly. My father never had a traditional retirement either.
After his years in the Navy, he took a job at a Firestone store in Wichita, Kansas — a short, forgettable chapter. It ended the day he met a man who’d made more money selling a single set of cookware than my father was earning in an entire week. He quit not long after and became a cookware salesman himself, then a franchisee, while still a young man. From that point forward, for the rest of his life, he never again took a salaried or hourly paycheck from an employer.
Eventually he moved into an independent landscaping business, and the only real wealth he ever built was tied up in a piece of land he’d bought for the nursery — land that, years later, became genuinely valuable. But my father never got to enjoy that value. By the time he was ready to sell, he was already sick, growing weaker by the week with a rare lung disease that would eventually take his life. He kept working the business anyway, right up until an offer finally came that he couldn’t refuse. He was eighty-two. He died not long after, having spent his entire working life without a single paycheck from anyone but himself, and without ever cashing in on the one asset that might have changed his final years.
I think about that legacy more now than I ever expected to.
My father was born into a world where the average American lived to be about forty-seven. By the time I came along, that number had climbed toward seventy-nine, and it hasn’t stopped climbing since. Neither of us was ever handed a retirement system built for the number of years we’d actually end up living. His generation barely had time to enjoy a traditional retirement even when they’d earned one. Mine is being asked to fund twenty or thirty additional years that nobody’s parents ever had to plan for.
What I Didn't Do
When I was younger, I told myself I had plenty of time to get ready for whatever retirement would eventually mean for me. I didn’t save in any serious way. I didn’t build the kind of assets that generate passive income while you sleep. I believed, without ever really examining the belief, that I could always earn my way out of whatever financial trouble came along. I was wrong about that. Dead wrong.
I knew, somewhere in the back of my mind, that this reckoning was coming. I just never felt like I had enough left over, beyond covering our living expenses, to set anything meaningfully aside. That’s not an excuse. It’s simply what happened, year after year, until the years ran out and the choices narrowed.
I’ve since learned I’m in far more company than I ever imagined. Retirement researchers now openly describe something close to a retirement savings crisis in this country — nearly half of Americans between the ages of fifty-five and sixty-six reach that stretch of life with no personal retirement savings at all. That statistic used to embarrass me, privately, as though it were a verdict on some personal failing unique to me. I don’t experience it that way anymore. It’s not a footnote. It’s most of us.
Still Building
So here I am, in my eighties, still working every day — not out of some noble refusal to slow down, but because I’m building something that has to work. I’m trying to create a business with enough value, whether through the income it generates or the value it could someday be sold for, to make sure Bonnie is taken care of, and to leave something behind for my family. I won’t pretend that doesn’t feel like a weight I placed on myself. It does. But I try not to dwell in that regret longer than it’s useful. Mostly, I pray for the strength, the clarity, and the health to see the vision through.
There’s actually a term now for what I’m doing, though I didn’t know it when I started: some researchers call it unretirement — the growing pattern of men returning to work, building something new, or simply never fully stopping, well past the age their parents would have considered retirement complete. Most of the writing on unretirement assumes it’s a choice, something men do for stimulation or purpose once the money question is already settled. I don’t think that’s the whole story. I suspect a lot of unretirement isn’t chosen so much as required — men my age still building, the same way my father did, because the traditional foundation of retirement was never actually laid beneath us in the first place.
A lot of unretirement isn’t chosen so much as required — men my age still building because the traditional foundation of retirement was never actually laid beneath us.
Retiring the Word
I’ve come to believe the problem was never really me, or my father, or the men like us. The problem is the word itself — a word built around a specific twentieth-century arrangement of pensions and gold watches that a lot of us never had access to in the first place, whether by choice or by circumstance.
My father worked until illness finally stopped him at eighty-two, still building toward a payoff he never got to collect. I don’t know exactly how my own story ends, but I know this: I’m not behind some schedule I failed to meet. I’m doing what he did, and what men like us have always done — building, right up until we can’t anymore, because nobody ever handed us the alternative.
