Why You Miss People from Work You Were Never That Close To

Last Thursday night, I found myself at a hotel bar at 10pm. I was very proud of myself for staying up so late. I know, I know – retirement means I don’t have to get up early. But the truth is, I’m an early-to-bed kind of person.

I was out with my cousin, who was visiting from Boston and is significantly more of a night owl than I am. We’d been to a comedy club. And I didn’t want to disappoint her by getting home too early. So I suggested one cocktail at a swanky nearby hotel, and off we went.

When we arrived at the bar, I noticed them immediately: a large group of people from a conference. You could tell because they were still wearing name tags, all from the same organization. Different ages, different backgrounds, all animated and talking over each other in that particular way people do at the end of a conference day – full of ideas, loose from the cocktails, glad to finally be out of the session rooms.

The women had clustered together at one end of the bar. The men were at the other. Everyone was in full networking mode.

I watched them for a moment and felt something I didn’t quite expect.

Not envy, exactly. Not nostalgia. I found myself thinking about all the conferences I used to attend – the nice hotels in fun cities, the cocktail hours I always dreaded walking into, the colleagues from across the country I’d see once or twice a year. And I realized: I don’t miss the conferences. But I do miss what they gave me.

That distinction took me a while to understand.

The Social Connection That Came with the Job

When I worked at a university, I traveled to conferences regularly. Over the years, I became friendly with colleagues from across the country. We’d catch up on each other’s projects. We’d hear about each other’s families. We’d have dinner and laugh and feel, for a few days, like we were part of a larger community of people who cared about the same things.

Back at the college, there were the people I saw daily – teammates and collaborators I’d spent years working alongside. I knew what stage their kids were in. Eventually what colleges the kids were applying to. I knew who was going through something hard and who had just gotten exciting news. That daily contact felt genuinely good. The kind of easy, built-in connection that doesn’t require any effort to maintain. It’s just… there.

What I didn’t fully understand until I retired was how many of my daily social needs had been met by my job – the sense of being known, of seeing familiar faces, of having people around who were glad to see me – without me having to seek any of it out.

Looking back now, almost a year into retirement, I can see honestly that I don’t have friendships with most of those people anymore. I enjoyed the relationships while I had them. I liked those people. But the relationships were situational. They existed because we worked together, traveled together, shared a professional context. Like being friendly with a neighbor – warm and real while it lasts, but not something that typically survives a move.

That’s not a criticism of those relationships. It’s just an accurate description of what they were.

Why This Happens — and Why No One Warns You

Repeated contact with the same people tends to create liking – even without deep conversations or shared values. Simply being around the same people regularly – in meetings, in the hallway, at the coffee machine – builds a sense of familiarity and warmth over time.

Work supplied this effortlessly. And along with it came something else that’s easy to overlook: the everyday, low-key moments that make you feel like you exist in someone else’s world. The colleague who always says good morning. The team that knows the inside joke. The person who asks how the weekend was and actually remembers what you said. These aren’t deep friendships. But they create a steady sense of being seen. Work provided them for free.

Studies show that retirement itself doesn’t cause loneliness. But it removes the structure that was providing connection – and eventually we figure out which relationships were deep enough to survive outside of work.

Most of us don’t realize how much of our daily social connection had been built into work – until the workday disappears.

The Checkout Clerk Moment

I’ll be honest about something that’s a little hard to admit.

There are days in retirement when I make more effort to chat with the checkout clerk at the supermarket than I ever did when I was working – because sometimes that’s my main social interaction outside of time with my husband.

If it sounds a little sad, it is a little sad. And I think it’s more common than most of us let on.

Retirement hands you unstructured time where the workday used to be. And what you discover, standing in that open space, is exactly how much of your daily sense of connection was built into the schedule.

What Chosen Connection Actually Looks Like

A few months into retirement, two friends had the idea to bring together a group of women they thought might enjoy each other. The five of us started getting together for dinner once a month. We named ourselves after the first initial of each of our names and call ourselves the WACKE Pack.

We’re slowly getting to know each other. We’ve made art together, gone on e-bike rides, played games. There’s an innocence and hopefulness to it – women in their late 50s and 60s intentionally building friendship at this stage of life.

What we’re building is different. It’s slower. It requires more initiation. But there’s something more solid about it – because we actually picked each other. Nobody has to be there.

A study found it takes roughly 50 hours of time together to move from acquaintance to casual friend, and more than 200 hours to develop a close friendship. Here’s the part worth sitting with: hours spent working together don’t count as much. The work time built familiarity – but it wasn’t accumulating toward the kind of closeness that outlasts a career.

That explains a lot, doesn’t it?

Where to Start

A few things have helped me and the women I work with:

Start with an Honest Audit

Look at the connections in your life right now. Which ones exist because of proximity or circumstance – a job, a neighborhood, an organization? And which ones would survive a retirement or a major life change? That gap is worth knowing. It’s not a depressing exercise. It’s a clarifying one.

Don’t Wait Until You Feel the Absence

The best time to build new connections is before you feel acutely lonely. If you’re still working, start thinking now about which relationships you’d want to invest in and carry forward.

Start Low-Stakes

You don’t need to find your new best friend immediately. A class, a club, a regular volunteer commitment – anything that creates repeated contact with the same people over time. The WACKE Pack didn’t become close overnight. We’re still becoming.

Let Someone Connect You

One of the most effective ways to meet people at this stage is through someone who already knows you both. Tell the people in your life that you’re looking. That’s how the WACKE Pack started for me. It changed things.

The connection you want in this chapter isn’t going to arrive automatically the way it did at work. But it can be built — deliberately, at whatever pace feels right for you.

If you’re also navigating the identity questions that come with this transition – the “who am I now that work isn’t defining me?” piece — I wrote about that too: Why Retirement Feels Harder for High-Achieving Women.

A First Step

This chapter takes time to design. And the social piece is one of the most underestimated parts.

If you’re navigating this – whether you’ve recently retired, you’re still deciding, or you’re a few years in and still finding your footing – my free Retirement Vision Starter Kit is a good place to begin. It’s a short, guided reflection to help you get honest about what you want this next chapter to actually feel like – in your relationships, your daily life, your sense of purpose, and the experiences that make you feel most alive. It takes about 20 minutes, and most women tell me something shifts just from working through it.

Here’s what’s inside:

• A guided reflection on how you want to feel in your relationships – and what’s missing.
• Questions to help you name what you want more of and what first step might get you there.
• Space to get clear on your daily rhythms, sense of purpose, and what a genuinely fulfilling day looks like.
• A section to capture the vision you’re starting to build.

👉 Download the free Retirement Vision Starter Kit

Let’s Have a Conversation:

What’s one social connection from your working years you miss more than you expected – or one you’ve been intentionally trying to build since retiring? I’d love to hear in the comments.