When Friendship Stops Being Automatic

On effort, asymmetry, and choosing connection

As I approached retirement, I worried a bit about how I would maintain social ties with my colleagues and friends at work.  Like many career-focused people, my circle of friends largely revolved around work.  I’ve got way more LinkedIn contacts than Facebook friends. When 90% of your social life is work-adjacent, what happens when that framework isn’t around anymore?

I actually started seeing this in the latter years of my career, working in a geographically scattered organization, with remote work options encouraged even before the Covid-19 era.  After-hours functions dwindled to almost nothing. So even before I retired, it was a challenge.

My friends at work tended to be in one of two groups: my peers and managers with whom I’d worked for a long time, and were close in age to me; and younger teammates whom I’d mentored, most with young families and very busy lives.  As I thought about maintaining those friendships, I knew that some were bound to fade away. 

I knew the burden would lie heavily with me to initiate contact and make the effort to keep in touch; after all, I’m the one with more time on my hands.  I try to be the one who turns the general, “we need to get together and catch up”, to “yes, let’s!  I’ll ping you next week to see when works for you.”  The habits of scheduling and follow-up haven’t left me.  Most relationships are a bit asymmetrical at any given time – that’s natural and okay.  I think the trick is to just recognize when the effort seems too one-way. 

I do appreciate, though, that my small circle of friends (casual and close) is not big enough to keep me  from being isolated.  As a solo retiree (living solo for the past 5 years since becoming an empty-nester) I don’t have a partner with their own social circle to leverage.  I’m going to need to expand mine.  I’ve found a few paths, just exploring my interests – golf lessons have introduced me to a lovely group of other retired golfers, and my passion for cruising has led me to a community of retiree cruisers that I have loved traveling  with.

I’m less worried now about maintaining work (and other) friendships.  I’m learning that effort isn’t something to resent — just something to notice. Retirement doesn’t just free your time. It offers that chance to actively decide what to do and with whom to do it.  In many ways, work made friendship automatic.  Retirement makes it intentional.

The Day After the Last Day

What panic, purpose and a rainy Monday taught me about reinvention.

The countdown to that special day—the last day of work—can be exquisite. You’ve given your notice, and now you’re checking off exit tasks, handing off projects, answering SO many questions. And hearing, “I wish I could come with you!” It feels wonderful.

For me the end of that countdown was a Friday, March 8th, 2025. That weekend I dismantled my home-office desk, the place where I’d sat for so many 12-hour days and taken so many Teams calls. It felt important to draw the line cleanly: I’m not working anymore. The party has begun. I packed up my laptop for return, tossed the stack of old notepads, and posted the desk to a neighborhood give-away page. It was gone within an hour—my old workspace carried out by a stranger.

I had spent years planning the financial side of retirement. What I hadn’t planned for was the abrupt disappearance of my work identity—the part of me that had been validated for decades.

So when Monday rolled around (a cold, rainy, dismal Monday), panic set in. After all the preparation, research, and anticipation of “living my best life,” the reality of not logging on—not being needed—knocked me sideways. What do my days look like when no one needs me? I’d always heard that men feel this loss of the work persona more acutely, but in that moment I realized it has nothing to do with gender—it’s about identity and purpose. And it hit me hard.

A day later, after some honest reflection, I reminded myself that the same qualities that earned me respect at work—clarity, problem-solving, reliability—would still serve me in retirement. And I’m convinced that if the weather had been better, the panic would’ve been far less dramatic. By Tuesday my inner monologue had shifted to: “Okay. Deep breath. You’ve got this.” I had a whiteboard full of small projects and several trips already booked, starting with a short cruise at the end of March. I picked something small, put my hands in the dirt in the garden, prepped for that first trip. A rhythm began to form.

I’m not under the illusion that chores and travel will ever give me the same validation I got from work. But they were a beginning—a springboard into figuring out what a meaningful life in this phase might look like. Small steps. Repeatable ones. Adding a little structure to an empty calendar gave me something to build from.

I can’t say I’ve discovered my life’s purpose yet. And that’s okay. Purpose isn’t a lightning strike—it’s something you uncover through exploration and experimentation. And for the first time in decades, I finally have the space to follow where that exploration leads.

Writing My Own Script

Retirement, reinvention, and figuring out what comes next

When I retired in March, it wasn’t a leap so much as the final click in a long chain of decisions. I had spreadsheets, milestones, payoff dates, contribution targets—the whole orderly march toward freedom. After years of rising stress in my fifties, the plan became its own kind of lifeline. Being a banker, I naturally obsessed over the money, but I also inhaled every bit of lifestyle advice about how to “prepare” for retirement. By the time I hit 60, I thought I knew exactly what life on the other side would look like.

So I turned in my badge, said my farewells, and stepped into retirement ready for slow mornings, no traffic, and the promise of travel and unhurried hobbies.

Fast-forward to November. Slow mornings absolutely hold up. Since March I’ve been on five cruises (a little over the top, sure), picked up golf again, and basically treated 2025 as a well-earned victory lap. All planned, all enjoyable, and honestly—necessary. After years of watching burnout become the default setting for people my age, it felt good to claim a year that was mine.

But as the holidays approach, something quieter is taking shape: the understanding that the celebration phase is finite, and the real work of retirement is about to begin. Not “work” in the punch-a-clock sense, but the daily choices that keep this stage of life intentional rather than accidental.

Nine months in, I’m not bored. I like the slower rhythm, and I have more projects than hours. Yet I can see how easy it would be to slide into familiar ruts—too much screen time, eating whatever’s convenient, letting days blur simply because no one is expecting anything of me. Without a big trip or shiny event, the autopilot habits start creeping in.

So the challenge now is to build enough structure to feel awake and engaged, without strangling the freedom I’ve worked so hard to earn. It’s a balancing act, but a good one: crafting a life that isn’t just pleasant, but deliberate. Retirement didn’t end the need for intention—it made it non-negotiable. I’ll be writing more as I figure out what a deliberate life actually looks like in practice.