Dealing With Regrets in Middle Age


People who say they have no regrets are liars or fools — they’re either putting on a good show or completely out of touch with reality. Me? My regrets are piling up by the day. But I’m learning that regrets can be spiritually healthy things.

Middle age: Counting the things I’ll never be

Not too long ago, I realized I think more about the past than the future. I’m not sure when it happened, but someone flipped a switch and instead of dreaming about all of the places life might take me, I spend way too much time dwelling on the places I’ve already been and the decisions that got me there.

I’m mostly content with the choices I’ve made. It’s the choices I didn’t make that bother me. For example, the other day I watched a movie about a guy who was a collector and auctioneer of high-end art pieces. The character’s life looked pretty interesting and I started wondering what my life would have been like if I’d pursued art collection as a career path. Before I knew it, I’d done the mental math and figured out I don’t have enough time left to learn about art, build a collection and hone my skills as a fine art auctioneer.

To be honest, a career in the art world was probably never in the cards for me. But you get the picture. I wrestle with the regrets about actual possibilities I didn’t explore, life paths I didn’t go down for one reason or another.

Now, it’s too late. I’m too old. There are too many things I’ll never be. Maybe that sounds familiar. Maybe you’re starting to count the things you’ll never be, too. It’s small comfort, but you’re not alone.

Regrets are part of the human experience

It’s a shame that regret is usually seen as unspiritual — evidence of a lack of faith. But I don’t think that’s how God works. I think God sets us on a path, points us in a direction and leaves the details up to us. That’s what free will is all about. Regrets aren’t evidence that we lack faith. Instead, regrets are symbols of our humanity.

But many of us still see regret as a sign of spiritual weakness, even though it’s front and center in Christianity’s defining event: the crucifixion. In Matthew’s gospel, we read that after three hours on the cross,

Jesus cried with a loud voice, “My God, my God, why have you forsaken me?” 

If you believe Jesus didn’t think the paths he didn’t go down in life, the possibilities he never explored while he was hanging there on the cross, then you really are a fool. As God-made-flesh, Jesus experienced the full range of human emotions. And regrets are an inescapable part of the human experience.

The trick is learning how to channel our regrets into something healthy, constructive and spiritually enriching.

Regrets aren’t failures. They’re blessings

Failure isn’t such a big deal when we’re young. It’s discouraging, but we tell ourselves that there’s still a lot of time left on the clock. Plenty of chances to explore new possibilities and finally get it right.

In middle age, our delusion starts to fall apart. The “what could have beens” begin to feel like failures. That’s the moment our regrets become spiritually fatal. Instead of launching points for spiritual growth and maturity, our regrets become black holes that suck the meaning out of our pasts,our presents and our futures.

In her book, The Gift of Years: Growing Older Gracefully, Joan Chittister describes the difference between healthy and unhealthy regret:

The burden of regret is that, unless we come to understand the value of the choices we made in the past, we may fail to see the gifts they have brought us.The blessing of regret is clear — it brings us, if we are willing to face it head on, to the point of being present to this new time of life in an entirely new way. It urges us on to continue becoming.

Denying our regrets is pointless. By acknowledging and naming them, we can better appreciate how the choices we made (not the choices we didn’t make) have formed us into the people we are today. And by understanding the blessing of those choices, we become more available to whatever God has for us in whatever time we have left.

In other words, our regrets aren’t failures. They’re sign posts that point us toward the people we are and the people we’re becoming.

Like it or not, you and I only have ourselves to blame for the choices we’ve made in life. But I’m learning that regrets aren’t really about blame or failure. Regrets are about being grateful for the blessings those choices have produced and the people they are enabling us to become.


Follow Us

A Spiritual Almanac daily podcast and weekly videocast
A Spiritual Almanac on Apple Podcasts
A Spiritual Almanac on Spotify
A Spiritual Almanac on Google Podcasts
A Spiritual Almanac on Amazon Music
A Spiritual Almanac on iHeartRadio
A Spiritual Almanac podcast on Stitcher

Pin It on Pinterest

Share This