When the Circle Closes: Retirement, Loneliness, and the Case for Connection

I remember visiting my mother in her final years and thinking that her world was shrinking.

My father, her husband and lifetime companion of over sixty years, had passed five years earlier. Her wide circle of friends was fading due to illness and loss. Even her physical world had begun to close in. She rarely left her condo, not even for a short walk around the grounds.

On the surface, she seemed content.

She had her routine, her daily Word Jumble puzzle, regular visits from family, and a steady stream of home health aides. She was never physically alone. But I still worried that she must feel lonely. She never complained, though. The most she’d say was, “Getting old is not for the faint of heart,” or something a little more... unfiltered.

In hindsight, I wonder if it was by quiet, even unconscious design that my mother chose to withdraw from the world around her. She preferred her own company over that of others. Maybe it was a result of physical limitations. But I don’t think it was depression. More likely, it was her way of preparing to leave this world when the time came.

Whatever the reason, it was foreign to me. Even now, ten years later, it still unsettles me. For me, friendship, connection, and social engagement are like oxygen. I need them to keep breathing. The thought of giving them up voluntarily feels like a bridge too far.

But then again, I’m not 90 years old.

I just turned 65 this month. Got my Medicare card. If I’m fortunate enough to reach her age, maybe I’ll see it differently. But for now, I can’t imagine letting my world shrink. I can’t picture my circle closing in around me.

That said, I’ve been thinking a lot about retirement lately. Reading articles. Asking friends, neighbors, and even strangers about their lives post-career. Lurking in Reddit threads. Writing a book.

And it hit me. Retirement doesn’t always feel like a gentle slowing down. Sometimes it feels like someone took an axe to the anchor chain that kept you tethered to community and conversation.

Think about it. For thirty years, most of your social capital is invested at work. Colleagues, clients, meetings, and even email threads are the lifeblood of each day. Then, suddenly, you retire. Sure, you all say you’ll stay in touch. But the truth is, the boat moves on, and you’re not on it anymore. That steady stream of interaction vanishes almost overnight.

We invest real dollars in our 401(k)s so that we’re financially ready for retirement. In much the same way, we spend decades building social networks, investing in conversations, collaboration, and community. But there’s no rollover plan for your friendships. No automatic distribution. No guaranteed payout.

And that’s where many people hit a wall.

In nearly every conversation I’ve had and every comment thread I’ve read, one theme keeps surfacing: loneliness. The pandemic may have sparked it, but the Baby Boomer wave into retirement has accelerated it.

Now, at this point, you may be worried about me. Poor guy, retired and talking about loneliness.

But you’d be wrong.

When it comes to connection, I’m not a tapas plate. I’m the all-you-can-eat buffet at Golden Corral. Conversation and connection are kind of my thing. My family might have a less flattering name for it.

I strike up conversations with waiters, cashiers, people in line, and yes, sometimes right in the middle of a pickleball game (to my partner’s dismay). I’m a human networking machine, powered by equal parts intellectual curiosity and an unshakable thirst for connection.

But I know not everyone operates that way. For many, the instinct in retirement is to shrink inward. To withdraw. To say, “I just want to read books and take walks alone.” And while solitude can be soothing, isolation is something else entirely. And it can do real damage.

Science backs this up. Researchers at Northwestern University have spent years studying “superagers,” people in their 80s whose memory and mental sharpness rival folks decades younger.

Their lifestyles vary. Some exercise. Some don’t. Some eat kale. Others eat Pop-Tarts. But across the board, they stay socially connected.

They talk, laugh, argue, and stay involved in their communities. They value friendships. They engage. And their brains, some with the same physical signs typically associated with Alzheimer’s, don’t show the same cognitive decline.

So, if sociability is the key to aging well, as Carl Spackler once said in Caddyshack: “I got that going for me, which is nice.”

There may be bumps ahead, but I’ve got my people. Loneliness won’t be riding shotgun.

Here’s the good news: staying socially connected in retirement isn’t complicated. But it does take effort. Old communities fade, so you’ve got to build new ones.

For me, it started with pickleball. I found exercise, laughter, competition, and, most importantly, new friends. Some of them, if you asked, might say they wish I had never retired. (I talk a lot.)

I also found intellectual engagement and connection through volunteering with the Small Business Administration. And I’ve made a real effort to keep in touch with friends from my long career. It takes energy. But it’s energy well spent.

My mother’s circle grew smaller in her final years. And yet, even then, she still reached out. Several times a week, my phone would ring. She wanted to share the day’s Word Jumble with me. Just a little connection. Just enough to keep the circle from closing completely.

If only it would ring again, just one more time.

Dan Troup is The Sunny Side of 57. He loves to reflect and write about life, family, career, and retirement. Check out more of his reflections on his blog site. Also, consider subscribing to The Sunny Side of 57. When not playing pickleball or hiking with Sue and Rigby, he (tries) to write a new post one to two times a month.