Liz Fosslien, the co-author of the book this month started with, has a drawing about regret that I keep coming back to.
It has two halves. In the top one, a small figure stands facing left, toward an arrow labeled “the past,” saying “I should have…” In the bottom one, the same figure has turned around. It faces right, toward “the future,” and it’s saying “What if I…” Above it, a short instruction: when you find yourself thinking the first, try asking yourself the second.
It’s a very simple drawing. It’s also, more or less, where this month has been heading.
This month, we’ve been looking at the feelings that come with change.
We started with the exhaustion of not knowing what’s going to happen. Then we looked at why someone else’s good news can sting more than we’d like to admit. And last Sunday, we asked what anger might be trying to protect.
Today, we’re looking at the feeling that often arrives afterward: regret.
What regret sounds like now
After a big change, regret tends to arrive in full sentences.
“I should have sold the house while we both could still enjoy the move.” Or the opposite: “I should never have sold it.” “I should have taken the trip while my knees still worked.” “I should have pushed the doctor harder.” “I should have called my sister before it got this awkward.” And after a death, the hardest ones: “I should have said it. I should have been there that night.”
Some regrets are about decades, not days. The years spent worrying about money that turned out fine. The career you stayed in because it was safe. The way things went wrong with a son or a daughter, and you’re still not sure exactly why.
The usual advice is to let go and look forward, which sounds lovely and helps very little at three in the morning. Regret at this stage of life can carry an extra weight: the fear that it’s too late to do anything about it.
What regret is pointing at
Researchers who have studied regret for decades have noticed something that changes how it looks: people often feel particularly strong regret in parts of life where they still perceive opportunities to do something differently. Psychologists Neal Roese and Amy Summerville gave this pattern a memorable name: “Opportunity breeds regret.”
That doesn’t mean every regret can be repaired. But sometimes the regret that keeps returning points to something you still want — and perhaps something you can still do about it.
Your sister might still be someone you could call. A class you never took might still be available. A trip you postponed could possibly happen in a smaller, different form. And sometimes the original opportunity really has passed, but what mattered about it hasn’t disappeared.
Some doors really are closed, of course. Losses don’t become manageable simply because we turn them into questions about the future.
So this Sunday’s question is not how to stop regretting. It’s this: which of your “I should haves” can still become a “what if I,” and how can you live with the ones that can’t?
What You’ll Find Below
The trouble with regret is that not every “I should have” can become a “what if I.”
Some doors are still open. Others have closed, and no amount of wishing will change that. The difficult part is knowing which is which — and what to do next.
Below, we’ll explore:
How to tell which regrets might still lead somewhere.
A short exercise for turning regret into a possible next step, without pretending every loss can be fixed.
What research suggests about living with regrets that cannot be undone, plus words for reaching out when another person is involved.
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