Retirement: Are You Keeping Busy or Building a Completely Different Life?
What might happen if you stop filling your calendar with activities and dates, and instead step into a period of exploration, discovery and unfolding?

One of the most surprising things I’ve learned from talking with retirees is that the people who seem happiest with how retirement is turning out are not the ones who saved the most, travel several times a year or have a calendar full of classes, lunch dates and volunteering.
In fact, they have little in common with one another apart from one specific thing: they are the people who remain open to learning, challenging themselves and seeking out experiences that take them out of their routines and comfort zones. As different as they appear on the surface, each one of them understands that while retirement means letting go of one’s career, it does not mean releasing their needs for connection, challenge and achievement.
Like a lot of people who’ve recently left work at the end of a lengthy career, I entered retirement (semi- in my case as I maintain a part-time professional coaching practice) with what I thought was a mapped-out vision of what comes next. I travelled to see my favourite 80s band, Simple Minds, play small venues in Paris and in Taormina, and finally got to the bottom of a handful of projects that sat neglected during my working years.
What I didn’t fully anticipate was in leaving my professional career, I’d quickly tire of spending my days looking for things to fix, make and do. Yes, the adage to keep busy is important—for our bodies, minds and sense of belonging. But what’s more important is understanding that retirement invites us to let go of the part of us we constructed throughout the decades of 40+ hour workweeks so we can make room for something entirely new to emerge.
All those years, our identities were reinforced by our roles. Be it manager, nurse, entrepreneur, consultant or executive, we knew where we fit. We knew what we were good at. We knew how to contribute. Then we hand in our badge, leave the building one last time and quietly, everything we built in our professional lives floats away.
I’ve seen a few colleagues retire and immediately attempt to recreate that familiar driven version of themselves. They commit to activities that provide structure, recognition or sense of accomplishment they had before, like sitting on a board or signing on to a part-time job doing something they enjoy. And for a handful of them, that meets enough of the needs that work once did.
Conversely, the retirees who struggle most are the ones chasing the status or identity they once had, trying to resuscitate the version of themselves that no longer exists. This latter group often end up unfulfilled and exhausted, waking every day to a vague sense of loss and disorientation, and unsure what fulfillment looks like without the title, position or rank they once held.
Then there are the people who take a completely different approach.
First off, they don’t rush into anything. They make it a priority to process the complex emotions that accompany this major life change, some of which involves grieving, letting go and acknowledging that a part of life is now behind them. They take stock of who they’ve become and allow themselves to loosen the professional identity that previously defined how they saw themselves. With time, they get to a place of asking themselves some form of the following question: Who else might I become?
“The shift from looking to replace what work gave me to exploring what life might now be changes everything,” a retired chief operating officer who picked up oil paints and discovered she’s an artist said to me during a recent session. She’s but one example. Then there are these people I’ve helped through their transitions:
The lifelong caregiver with a love of dogs who went back to school to become a part-time veterinary technician.
The former accountant who mentors at-risk youth two afternoons a week at the local community centre.
The entrepreneur, who spent forty years building a family business into a local chain of coffee shops, who now studies—and is learning to practice—Buddhism.
None of these identities were part of anyone’s original retirement plan. In fact, earlier iterations of each of these people would not recognize who they became once the scaffolding of work no longer held their sense of self together.
This the part of retirement we rarely talk about—the pathless transition that unfolds when we allow ourselves to step out of what we thought we wanted and into a period of becoming.
What I am getting at is this: the retirees who adjusted best weren’t necessarily more confident, prepared or hewing to some predetermined plan: they were simply willing to let interests emerge and for life to surprise them. At some core level, they trusted that the next version of themselves would reveal itself without jamming their calendars full of busyness.
In my own life and with the people I coach, I am learning that the real work of retirement is about giving yourself the time and space to discover what is possible as you let yourself become the you that you have yet to meet.
Thanks for reading. If you’d like a resource to reflect on the emotional side of transition to retirement, download this free tool.
And if you’re curious about my work as a retirement coach, visit me here.


