I Don't Miss the Work. I Miss The People.
Why Belonging Is the Most Overlooked Dimension of Retirement Planning
🟢 It is one of the most common things people say about retirement. And it makes complete sense. After decades of shared projects, shared struggles, and shared milestones, the people become the fabric of your working life.
But I think the statement deserves a closer look because what most people are actually missing goes deeper than the people themselves.
🧭 Work built your belonging infrastructure
Think about what work actually provided, quietly and invisibly, for decades…
It gave you people who expected you to show up. Colleagues who knew your name, your history, your habits. A team that needed what you specifically brought. A shared purpose that connected you to something beyond your own day.
You didn’t have to build any of that. It was built into the structure of the work itself. Every meeting, every project, every hallway conversation was creating connections (AKA: belonging infrastructure) without you ever having to ask for it.
Brené Brown draws a distinction that separates belonging (being accepted as you are in a place that genuinely wants you) from fitting in, which means changing yourself to be accepted. Work, at its best, gave us the first kind. It knew us. It needed us. We earned our place there over years and decades.
That is a harder thing to replace than most retirement planning accounts for.
And for people who spent twenty, thirty, or forty years in one organization, the depth of that belonging is even more profound. They didn’t just share a workplace. They shared life stages. Marriages, children, divorces in some cases, empty nests, and now retirement. That kind of shared history creates bonds that have little to do with job titles and everything to do with having been known by the same people through the full arc of adult life.
🌱 Three kinds of belonging and what happens to each
When I think about what work actually provided in terms of connection, it breaks down into three things that don’t automatically transfer to retirement.
The first is relational belonging — the colleagues, the team, the daily human contact that happened naturally as a byproduct of being somewhere together. These relationships often feel closer than they actually are outside the context of work. When the shared context disappears, many of them quietly fade, not because anyone meant for them to, but because the structure that held them together is gone.
The second is purposeful belonging — the sense of being part of something that matters, of contributing to a goal larger than yourself. This is the belonging that comes not just from being with people, but from building something with them.
The third is structural belonging — the simple, underrated experience of being expected somewhere. Of having a place that was yours, a role that was recognized, a presence that was noticed when it was absent.
Most retirement planning replaces none of these. It addresses the financial picture carefully and leaves the belonging infrastructure largely to chance.
💡 Belonging has to be designed, not assumed
The Harvard Study of Adult Development (one of the longest-running studies on human happiness) found that the quality of our relationships is the single strongest predictor of wellbeing in later life. Not wealth. Not status. Relationships.
Laurie’s story is one of my favourites for illustrating what intentional belonging looks like in practice. After twenty-seven years in municipal government, she and her husband bought a trailer, headed south, and joined a community of snowbirds in Palm Springs. For several winters, they returned to the same campground, reconnecting with the same people, building the kind of easy, unhurried friendship that busy working life rarely allows.
When she returned home, she didn't wait for belonging to find her. She joined a nonprofit board and was asked to serve as the volunteer mayor of her small lakeside village, a role that draws on her project management background and her love of community while keeping her firmly in retirement. She also became part of an events committee that plans themed gatherings… casino nights, flapper parties, Oktoberfest dinners and more. In the weeks before each event, the group gathers to make homemade pierogies and cabbage rolls, laughing and sharing stories as they cook.
“It’s about friendship as much as celebration,” she told me.
What Laurie understood, perhaps intuitively, is that belonging in retirement doesn’t arrive on its own. It is cultivated through communities joined, relationships deepened, and contributions made over time.
This is one of the tools I work through with people in my retirement transition coaching is called the Life Design Purpose Wheel. The Connection and Relationships dimension is important because the research is clear and the lived experience confirms it: the people who thrive in retirement are rarely the ones who waited for connection to happen. They are the ones who began building it, deliberately and early, while they still had the structure of work to lean on.
Making friends later in life can be harder than it was in our twenties. Shared context matters enormously, and that context has to be intentionally created once work no longer provides it. The lake communities, the travel companions, the exercise clubs, the volunteer boards… these don’t happen by accident. They happen by design.
✍️ A question for you:
When the “belonging” infrastructure of work falls away, where will you belong… and have you started building that yet?
Tammy Martins is a retirement transition coach, speaker, and author of Designing Your Second Act, forthcoming from Routledge in November 2026. She helps professionals and executives design a purposeful and fulfilling life after work.
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