I keep two invisible columns in my head, and you probably do also. One is labeled IGID — I’m Glad I Did. The other is IWIH — I Wish I Had.
When I look back, my IGID column is full of the moments that scared me, stretched me, or required a leap of faith. Those are the experiences that made me feel most alive — the ones that pushed me past comfort and into growth.
The IWIH column, on the other hand, is a quiet ledger of hesitation, laziness, and fear: the trips I postponed, the conversations I avoided, the dreams I filed under someday. When I think of these things, Chip Conley’s powerful question comes to mind:
“What will you regret 10 years from now if you don’t do it now?”
At 83, I’ve decided I don’t want to end my life with too many regrets about things I didn’t do. That’s why I’ve signed up to walk the Camino Primitivo, a 200-mile pilgrimage from Oviedo to Santiago de Compostela in Spain. Next April, I’ll take one more step toward the kind of life that fills the I’m Glad I Did side of the page.
Could I have chosen comfort instead? Of course. But I’ve learned that comfort is a deceptive and fickle friend. Growth, meaning, and joy live just beyond it — in the stretch zone where the body tires, the spirit strengthens, and the soul says, “Yes, this is what I came for.”
“Of all the words of mice and men, the saddest are, ‘It might have been.’”
— Kurt Vonnegut
Maybe aging well isn’t about clinging to youth at all. Maybe it’s about keeping the IGID column growing — saying yes to adventure, curiosity, and connection — right up to the very end.
So, as you think about your own life, here’s a question worth pondering:
What belongs in your IGID column — and what’s still sitting in IWIH, waiting for you to act?
🥾 Breaking Age Update: The Camino Challenge
Next April, I’ll walk 200 miles across northern Spain on the Camino Primitivo, one of the most ancient and demanding routes to Santiago de Compostela. I’ll be 84 when I do it — proof that big things are still possible at any age.
This journey isn’t just personal — it’s a fundraiser for Breaking Age, our nonprofit dedicated to helping people flourish in the second half of life. Your support will help us offer free and low-cost programs that challenge age stereotypes and create spaces for growth, purpose, and connection.
Stay tuned for updates, reflections from the trail, and ways to support or walk alongside me — in spirit or stride.
🕊️ Because life’s too short for an IWIH column that’s too long.
This article was originally published on Breaking Age.