“I’m afraid I waited too long. It’s too late and I’m too old.”
It’s a common fear in retirement, the belief we missed out on a dream harboured in youth. The antidote is simple but not easy.
When my client logged on for our bi-weekly coaching session, she started the conversation by telling me she had done the homework I suggested: making a list of experiences she still wanted to have before she could no longer have them.
She had recently retired after a successful career in human resources, having started decades ago as a pension and benefits specialist, and over the ensuing years, worked her way up to an executive role, leading the People and Culture portfolio at a teaching hospital in a mid-sized Canadian city.
On paper, she had done everything right. By using her employer’s matching pension program and setting aside additional money in a tax-free savings account each year, she was financially prepared. Thanks to this thoughtful planning, she had the resources to live comfortably and more time than she’d had in decades. Today, we were scheduled to go over a list of activities, experiences, and opportunities she wanted to fill in her wide-open calendar.
Moments into sharing her modest list, she told me she was embarrassed. When I gently probed what was causing the embarrassment, she took a deep breath.
“I’m afraid I waited too long. It’s too late and I’m too old. There, I said it.”
Given what I knew about her financial situation, it was clear this wasn’t about money. Instead, she was talking about dreams tucked away in the corner of her mind while she built a career, raised a son, cared for her aging parents, and kept her household running.
An avid reader who loved attending author festivals and hosting a neighbourhood book club for almost a decade, she made being a writer the top item on her list. “I know it’s stupid, and there are already so many books out there,” she added, “but I’ve always wanted to create something that’s mine.”
I nodded. “And now you have the freedom to finally pursue your writing. What would it be like to give yourself the time to explore this?” I asked, knowing that if we gave her dream a bit of fuel, she’d tap into the excitement and anticipation of finally starting out on a journey long set aside.
“Amazing! I’d feel like I was doing one of the things I always hoped I’d do.”
I’ve had these conversations before, so I knew what was coming next…
“But what if I’m not good enough?” she mumbled, lowering her gaze. “Or I can’t finish what I start? Or it’s too hard?” Then came the biggest what if of all: “What if it’s simply too late to start?”
It’s a fear I hear often.
Many people enter retirement carrying a truckload of unrealized dreams. Some are big, like writing a book, starting a craft business, or exploring the seven wonders of the world. Others are quieter but no less important: dabbling in ceramics, learning to speak Portuguese, becoming more involved in local politics, or volunteering to walk dogs for the local Humane Society.
These dreams often have roots in our youth and rarely diminish with the passing of years. Like seeds in frozen ground, they wait until the thaw, when conditions become auspicious, as they do in retirement.
Initially, this can be exhilarating. The yoke of work is off, and we’re free to do what we want when we want. But that’s not the full story. Like my client, we can also be terrified. Why? Because pursuing an unrealized dream requires something many of us haven’t practised in decades and are loath to face: being a novice.
As we built our careers, we became experts. We knew what we were doing, having acquired know-how, credibility, and authority over the years. For the newly retired, a surprising amount of uncertainty can bubble up, regardless of how competent or confident we felt when we worked.
I, for one, was used to designing leadership programs I knew would succeed. Then I left full-time work to create a modest half-time coaching practice and had to face the discomfort of no longer identifying with a role — and the validation that came with it — that once defined me.
But if the purpose of retirement is to have all the answers, what’s left to discover? Did we work all those years just to have worked all those years? Maybe the what-if to ask at this stage is: What if I lean into the space and accompanying discomfort retirement offers and discover what I most want at this time in my life?
And let’s be clear: the dreams any of us carry into retirement are not evidence of what we failed to accomplish. They are breadcrumbs, leading us toward the parts of ourselves that still want attention, the parts that are still curious, creative, and seeking expression.
As for my client, she left our coaching session with something far more meaningful than a to-do list or a plan. She left with the permission to begin.
Because the truth is, the most meaningful chapters of our lives don’t come from a plan. They come when we allow ourselves, as my client finally did, to write ourselves into a life we really want one word at a time.
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.