All my friends are retired. Why am I still working?

Laboring on into one’s 60s adds the complication that a goodly number of one’s friends and associates have called it quits. Once consumed by jobs and family obligations, they suddenly have time on their hands.

And they will assume you do, too, especially if you work at home. Just as the sirens were said to lure ancient Greek sailors to their death, one’s retired friends can be fatal to productivity, even if their song only takes the form of text messages.

It’s fun, of course, to meet for lunch, and more fun still to linger. But why not stop to look at some art afterward? There is a great exhibit showing, and then we can talk about it over a drink or two. One can always work in the evening.

That was the same thing I told myself recently when a retired neighbor persuaded me to devote most of a recent weekday afternoon to golf, something I hadn’t played in 30 years. That evening unfortunately was spent not catching up on work but recuperating from a strained forearm, countless insect bites and lingering intimations of heat stroke.

Now that my wife has retired, she has taken up the role of Siren in Chief. There is always something to fix, plan or discuss, and it’s all surprisingly alluring compared with the pressing need of earning one’s daily bread. Besides, it makes sense to visit museums or big box stores on weekdays, when such places aren’t thronged. And after so many years of work, it seems churlish to resist playing hooky with her on occasion now.

Bad financial timing

Unfortunately the siren songs of all these retirees come at the worst possible time, professionally and financially. The loss of my wife’s earnings has made my own meager scavengings all the more important. Yet many of the editors who once provided me paying assignments are themselves calling it quits for a life of leisure.

Meanwhile, the song of retirement is sounding more melodious than ever. Tiresome difficulties relating to work, ever present even under normal circumstances, at my age prompt fantasies of hammocks and mai tais. I had planned on writing villanelles and studying ancient languages right about now. But like the conscientious gratification-postponers we have always been, Louise and I are trying to put off Social Security until we are 70—and then live long enough to make the decision pay.

I can see the advantages of our newly mixed marriage. In these still-healthy years—may they long endure!—there is a special opportunity for each of us to pursue interests that the other doesn’t share. Thus, as I write these words, Louise is off in Iceland, happily combining her passions for hiking and knitting. In her absence, I am free to indulge my love of sitting at my desk and tearing my hair out.

Still, who am I kidding? My favorite thing is working. As to my retired friends: Not only do I enjoy their availability, but I learn a lot from their example. Liberated from their toils, these old pals are the unwitting canaries in the coal mine of aging, providing vital information to the rest of us about life after work. Some of them are plainly thriving; I have never seen them more cheerful and relaxed. They sleep better, exercise more and see more of the people they care about. Some serve on boards, give talks or even write books.

But others frankly seem lost, especially those who were bribed into retiring or just shoved out the door. All of them had demanding, even voracious, careers. But finding again the kinds of jobs they were used to is nearly impossible at our age, and most lack the instincts or experience for entrepreneurship.

One or two are victims of their own success, having sold a business or otherwise accumulated such wealth that they find themselves groping for what to do next. Nor is volunteering a slam dunk. One well-meaning friend, bursting with talent and energy, doesn’t want to collect tickets at the door or clean up after charitable events, but even unpaid work using her immense skills and experience isn’t forthcoming in the nonprofit world.

Back to my desk

What I have learned from these folks is to keep typing, whether it pays or not (which of course it never has). I enjoy goofing off with my retired pals, but it’s funny how often I seem to get a second wind late in the evening, and how easy it is to find my way back to my desk despite the distractions of the day. Not a bad metaphor, I suppose, for the reawakened sense of purpose I see in some energetic older friends who have embraced new outlets for their talents.

And that’s important, too. Reaping the rewards of work doesn’t necessarily mean holding on to a particular job. One retired autodidact I know has written a superb book, created sharp social-media satires, and made a hard-hitting documentary. Is this guy even retired?

Retirement may yet come for me, and if it does, I will be grateful to others who have shown the way. From them it’s clear that the retirees who truly thrive are those who relish their well-earned freedom but have managed to knit themselves into a resilient web of family, friends and personal passions. My sense is that it’s crucial—long before retirement—to cultivate interests and relationships beyond work, and to have some idea of where you are going to land before you yank the handle on the professional ejector seat.

Meanwhile, I take it as a good sign that my retired friends want to meet because the very worst thing I see among them is isolation. Avoid it at all costs, no matter how old you are.

Daniel Akst is a writer in New York’s Hudson River Valley. He can be reached at reports@wsj.com.