Most mornings start the same way. I sit down at my desk with a cup of coffee, open my computer, and get to work. There are articles to edit, podcasts to review, research to organize, contributors to check in on. No one is expecting me. No one is paying me. There isn’t a deadline anyone but me has set, and there’s no finish line waiting at the end of any of it.
And yet I’m eager to begin. Every morning. That’s the part that used to puzzle me.
For most of my working life, I understood exactly why I showed up. There was always another listing, another closing, another commission, another goal with a number attached to it. The job demanded it, and I met the demand. I enjoyed the work — I want to be clear about that — but the enjoyment and the obligation were tangled together in a way I never had to untangle. Today the obligation is gone. The eagerness isn’t. That’s new.
I’m eighty-one now, and I notice things about time I never used to notice — the way it moves, the way there’s a finite amount of it left to spend. I didn’t think much about that at my desk in real estate; there was always another year, another listing season. That’s changed. I’ll come back to what that shift means, because it turns out to matter more to this story than I expected.
It turns out there’s a name for what I was living without knowing it had a name. The philosopher Kieran Setiya, writing about midlife rather than retirement, draws a distinction between what he calls telic and atelic activities — a bit of borrowed linguistic jargon that turns out to explain something real. A telic activity aims at a finish: it’s done when it’s done, and once it’s done, that particular source of meaning is used up. Driving home is telic. Closing a sale is telic. An atelic activity has no finish line built into it — it’s realized in the doing, not in the completing. Setiya’s point is that a life built too heavily on telic pursuits is a life that keeps consuming its own meaning, one finish line at a time.
I spent thirty-eight years in a beautifully telic career. Every finish line crossed, cleared the way for the next one.
Every finish line crossed, cleared the way for the next one.
So when I read the research on goals in retirement, the advice I kept running into was some version of: stop chasing finish lines, learn to be present, find peace in the process. I understand why that’s the prevailing wisdom. But it doesn’t quite fit what I’ve found. I haven’t stopped setting goals in retirement. If anything, I’ve set more of them, and larger ones. What’s changed isn’t whether I have finish lines. It’s what’s on the other side of them.
The Encore Project doesn’t have a finish line in the old sense, and I hope it never does. No one is scoring it. No one assigned it a deadline. There may never come a day when I can honestly say it’s finished — and unlike the sale that closes or the deal that clears, I don’t want there to be one. What keeps me at the desk every morning isn’t the promise of a payoff waiting at the end. It’s the belief that every article, every podcast, every contributor’s story adds another brick to something that might outlast me. I still have goals for it. I want it to succeed. I hope, someday, it becomes financially sustainable — that piece I genuinely can’t picture yet, the one part of this that still feels unsolved. But even that goal doesn’t function the way a commission used to function. It’s less a finish line than a milestone on a road I don’t want to end.
That shift I mentioned earlier — the way time feels different at eighty-one — turns out to be part of the answer. I am, in a real sense, racing to a finish line. Every day. I know it, and I feel it — not as dread, but as fuel. I’ve done the math on the years I likely have left, and it isn’t abstract to me anymore. That awareness is with me most mornings before the coffee’s even finished brewing.
I’ve done the math on the years I likely have left, and it isn’t abstract to me anymore.
I used to think that urgency would be the enemy of a peaceful retirement — that the whole point of this stage of life was to finally stop racing. I’ve found the opposite. The urgency is what gets me out of bed with something to say yes to; without it, I suspect I’d be napping through the very years I claim to want to make count. Research on purpose in later life backs this up more than I expected — people with a strong sense of purpose have been shown, in a Harvard-led study of the Health and Retirement Study cohort, to face notably lower mortality risk over time than those without one. I don’t need a study to tell me that. I feel it most mornings. But that clock isn’t really the subject of this essay. It’s the thing that sharpened my attention enough to notice what I’m about to describe.
So no, I haven’t escaped the finish line. I don’t think anyone does, and I’m suspicious of anyone who claims to have. What retirement gave me wasn’t an exit from finish lines — it was the chance to choose new ones, for different reasons than the ones that drove me for thirty-eight years. Earlier in life, most of my goals were tied to earning a living, building a career, serving clients, supporting a family. Those were worthwhile goals. I don’t regret a single one of them, and I’m grateful for what they built. But they were, almost without exception, telic in Setiya’s sense — measured by results, visible and immediate, and finished the moment they were achieved.
The goals I have now measure something else. Not what I closed today, but what I built that will still be standing after I’m not the one building it. They measure contribution instead of transaction — whether a reader felt encouraged, or had an old assumption gently challenged, or simply felt a little less alone in this stage of life, because of something I wrote. They measure purpose more than performance — whether the work still feels worth doing on the mornings when no one’s watching. They measure growth I can’t put on an invoice: what I’m learning about writing, about other people’s stories, about my own life, simply by staying at this. And increasingly, they measure something like legacy — not a monument, nothing that grand, just the hope that a piece of what I’m building outlives the building of it. None of that shows up on a commission statement. All of it shows up in whether I still want to sit down tomorrow morning and do it again.
I don’t think this is only my story. Whatever your second chapter looks like — volunteering, mentoring, learning something new, building a business, making something with your hands, or a pursuit I haven’t even guessed at — the same question is probably worth asking. Not “have I set a goal,” but what that goal is actually measuring now, and whether it’s still the yardstick you used to use.
If there’s one thing I hope a reader takes from this, it’s not “stop setting goals in retirement” — I’d be a hypocrite to say that, given how many I’ve set for myself in the last few years. It’s this instead: don’t assume the goals worth keeping are the ones you can still measure by yesterday’s standards. Ask whether the goals you’re chasing now are helping you become the person you want to be during the years you have left — however many those turn out to be. The most satisfying goals, I’ve come to believe, aren’t the ones you eventually cross off a list. They’re the ones that keep giving your life meaning long after you started pursuing them.
The race isn’t over. I’ve just stopped racing toward the things I used to race toward — and started racing, gladly, toward the ones that might actually matter when I get there.
