Working Backwards From Regret for a Life Well Lived
#NoRegrets
My wife’s grandfather passed away recently. With his passing, all of our collective grandparents are now gone.
It’s a strange milestone. On one hand, it’s the natural course of life. But on the other, it’s a jarring reminder that time is always moving, and the people who shaped us don’t stay here forever.
In the days since, I’ve been thinking a lot about Bronnie Ware’s book, The Top Five Regrets of the Dying. She was a palliative care nurse who spent years listening to people in their final days, and she noticed the same themes came up again and again.
The most common regrets were:
I wish I’d had the courage to live a life true to myself, not the life others expected of me.
I wish I hadn’t worked so hard.
I wish I had the courage to express my feelings.
I wish I had stayed in touch with my friends.
I wish I had let myself be happier.
What strikes me is how none of these have to do with achievements, titles, or possessions. No one said, “I wish I had made Partner sooner” or “I wish I had bought a bigger house.” The regrets are about alignment—living in a way that reflects what matters most, not just what’s expected of us.
And that has me wondering: what if we worked backwards from these regrets? Instead of charging forward and hoping things turn out, what if we asked ourselves: If this is what people consistently look back on, how should that shape the way I live today?
For me, that brings up some uncomfortable but important questions:
Am I living in a way that’s true to me, not just what others expect?
Am I giving enough of myself to family, friends, and joy—not just work?
If I keep going the way I am, what regrets might I be writing for my future self?
I don’t have neat answers. Honestly, I’m still wrestling with the questions. But maybe that’s the point. Life doesn’t hand us clarity on a silver platter—we have to create it, one choice at a time.
This season of reflection is a reminder to pause, to look ahead, and to ask: What would I regret if I didn’t change? And then take even one small step in a different direction.