Last evening at the Bronxville Library, I met a roomful of people who had come to rethink retirement. Some were years away from leaving work. Others had retired long ago. Each had a different story, and no one was looking for a simple answer.
Some had been retired for 30 years and were still trying to figure out how to enjoy life outside of work. Several teachers were four or five years away from retirement and weary of what their work had become. One teacher was using his accumulated sick days to reach his birthday at the end of November, when he could retire. A woman had recently quit a job she had held for years. As colleagues left, more and more of their work landed on her desk, until she decided she had had enough.
They had all arrived at the same library, but they were standing at very different thresholds.
I gave everyone a copy of my Rethink Retirement workbook. Before we opened it, we listened to one another. That matters. We often talk about retirement as if it were a single event with a predictable path: save enough, pick a date, leave work, enjoy yourself. The people in that room reminded me how much that tidy story leaves out.
Then we began to work through the questions that help us design a life after work.
Who am I when my job is no longer my introduction? Identity can be harder to reshape than a calendar. A title, a workplace, and the people who count on us can become part of how we recognize ourselves.
What does a great ordinary day look like? I asked them to imagine a “perfect Tuesday.” A vacation is easy to dream about. Tuesday asks what time you wake up, where you go, whom you see, and what gives shape to the hours when nobody else has planned them for you.
Why do I matter, and to whom? Purpose need not be grand. It can begin with being needed by a grandchild, teaching someone a skill, tending a garden, serving a community, or finally making room for work you choose to do.
And then we came to community. For several people, this was the hardest question of all.
One teacher who had left his working life was exercising and enjoying his freedom. Yet he was lonely. His friends were still working. At 60, he felt younger than many of the retirees around him and wasn’t sure where to find companions in this new phase of life. He had gained time, but he had also lost the everyday contact that work had quietly provided.
What do you do with freedom when you have no one to share an ordinary Tuesday with?
The women preparing to retire voiced a different uncertainty. They knew they wanted a change, but they could not yet picture what would come next. The teachers smiled when they described summers as their retirement practice. They were ready for more summers. Yet even a familiar stretch of freedom does not fully prepare you for a life in which September no longer calls you back.
People who were enjoying this chapter offered a message to those approaching it: take charge of your life now. Start imagining, experimenting, and making connections before you leave. And remember that whatever you choose first does not have to be your final answer.
That last point can be surprisingly hard to accept. We want a plan that will make the unknown feel safe. But a new chapter is learned by living it. You might join a group and discover it is not your group. You might volunteer and find that you miss being paid for your expertise. You might plan quiet days and realize you want a fuller calendar. Each discovery tells you something useful.
In a new job, someone may show you around, introduce you to colleagues, and help you find your footing. Who onboards us into life after work? Too often, no one does. We are handed a farewell party and expected to know how to build the next 20 or 30 years.
Last night, for a little while, the library became a place to begin that work together. We heard the different ways people arrive at retirement: relieved, excited, exhausted, uncertain, lonely, curious. We put some words around the questions. We imagined a Tuesday. And we began to see that designing what comes next is a process, one that can change as we do.
If you are approaching retirement—or have been retired for years and still feel unfinished—try starting here: What would make an ordinary Tuesday feel like your own? And who would you want to share part of it with?
I would love to hear your answer in the comments.