Regret. It’s such a heavy word. But also a very human one.
A later-life reflection on making peace with the past, and choosing what comes next.
As we get older, especially in our sixties and beyond, regret can surface in surprising ways. Not always as dramatic turning points, but as quiet moments of reflection. We pause, we remember, and we think: I wish I’d done that differently.
We regret staying in jobs that drained us. We regret walking away too soon from something that might have worked. We regret not taking the leap, or taking it too fast. Sometimes, we simply regret how long we waited to choose ourselves.
But regret, while painful, isn’t useless.
We did the best we could at the time, with the knowledge, energy and support we had. Our choices were shaped not just by facts, but by fatigue, fear, family pressures, health concerns, or the need for security. Life is rarely clean or clear.
Even so, regret offers a signal: it reminds us what mattered, and still might.
So here’s the real question: what will we do now, in this next chapter of life?
If we’ve spent decades playing it safe, maybe now’s the time to take a small risk. Not a reckless one, but something that stretches us. For one person, it might be learning to play the piano. For another, it might be walking away from a friendship that no longer feels reciprocal.
I spoke recently with a neighbour about relationships. About people who stay in them for the children, the mortgage, or simply because change feels too hard. We do the same in other parts of life. We settle. And then we stay settled, long after the need to.
But I keep returning to a quote I read years ago:
“The space for what you want is taken up by what you settle for instead.”
Letting go is rarely easy. But sometimes, we need to release what no longer fits to create room for something new to take root.
When COVID brought my consultancy work to a halt, I could have clung to the familiar. But I chose to lean into something unexpected: becoming a woodland owner. That shift changed my life. If you’ve followed my Woodland Conversations, you’ll know how deeply connected I am to that space now.
Regret still visits me, but these days, I see it differently. I use it to ask:
- What do I still want to experience?
- What am I not doing that would bring more satisfaction now?
- What small risk could move me in the direction of the life I still want to live?
At the time of writing, I’m six weeks from turning 68. A part of me still marvels at that number. But I’m here. I’m still learning, still evolving, still dreaming. I have hopes for the next 25 years. I know nothing is promised, but I’m committed to living as fully and consciously as I can.
Because regret only has power when we stop growing.
And if you’d like to explore these thoughts further, I’ve recorded a short video from my woodland that continues the conversation. You can watch it here:
