Prevent a Regret Before It’s Too Late

You know there are different kinds of regrets, right? Different flavors of “ugh,” if you will.

Jodi Grade Nine Regret Hair

Exhibit 1.0: “The Regret Coiff”

There are regrets of commission: stupid things we said or did that we wish we hadn’t (like my hair in grade nine; see exhibit 1.0) These regrets tend to fade over time as we learn to live with our stupidity.

And then there are regrets of omission (*insert the “dun dun dun” sound*): things we didn’t take action on that we really wish we had (like studying outdoor recreation instead of corporate law, or saying yes to Arnie’s prom invitation). Researchers are clear that these “paths not taken” eat away at us until the day we die. It’s perfectly possible these regrets of omission gnaw at our souls in whatever afterlife we happen to believe in, too.

As a Stop Squandering Your Life crusader, I could care less about regrets of commission. Water (okay, sewage) under the bridge needs to flow the fuck away. We’re not here to moon over how we coulda shoulda woulda arranged our hair on freshman picture day (although I do have ideas on that, involving 60% less hairspray). What we are here to do is attack the regrets of omission, because many of them are still fair game to course-correct.

Our “paths not taken” fall into two categories: closed- and open-door regrets.

The open door of regretsClosed door regrets are admittedly shitty because the opportunity no longer exists to course-correct them. If you’ve been harboring the warm and fuzzies for Arnie all these years and then learn that Arnie died in a tractor accident, the door to your “maybe we could rekindle the magic we had” idea slams shut. It’s unfortunate (especially for Arnie), but again, not the kind of regret we’re concerned about here.

Open door regrets are where things get sizzly. These are paths not taken that still ~technically~ have potential to be traipsed down . . . like if you’re trying to muster the will to charge on as a corporate lawyer, you could ~technically~ get a gig in outdoor recreation after all. If Arnie hadn’t been mangled by the tractor, you could’ve ~technically~ reached out to see if that flame still flickered.

Examples! We like examples.

I recently worked with a group in a “100 Days Left of the Year” retreat—you know, the kind of event designed to get people de-squander-ifying their lives before the year ends and reminds them that all they did was work all year with nothing to show for 2023 other than hard-earned carpal tunnel syndrome.

So after warming everyone up by reminding them they’re all going to die (it’s really what I do best), I asked them to list their regrets of commission, omission—all the flavors and shapes and sizes of “ughs” and “coulda shoulda wouldas.” I then asked them to cross out their closed-door regrets (in a “that ship has sailed” kind of way). The next step was to highlight their open-door regrets in bright green highlighters.

  • “I never nailed that Mendelssohn piece on the piano,” one woman said wistfully, as though her hands had been amputated and she could never play again. From where I was standing her hands looked attached to her arms. I asked, “What’s stopping you from learning to play it, if you’d really like to?”
  • “I regret not asking my brother for forgiveness,” said another participant. Many nodded in the crowd, silently acknowledging their own tattered relationships. I asked, “What’s stopping you from asking for forgiveness now, if it really matters to you?”
  • “I wish I hadn’t wasted years worrying about my weight. I look at pictures from years ago when I felt unattractive, and from where I’m at now, I think I looked great back then. Will I look back on my photos of today, 10 years from now, and think I had it going on today? I’d regret not getting help with my body image.” (This anecdote bonded every woman in the crowd for life, naturally.) You know what I asked next: “What’s stopping you from working on that now with a great therapist, if it’s something that’s important to you?”
  • “I wish I had learned how to speak Italian,” one attendee admitted. YOU KNOW WHAT I SAID. If I knew how to speak Italian I’d have asked, “casa ti ferma”? Google translate told me that’s Italian for “What’s stopping you?”

We get stuck in our routines and our stories. We anchor into the narrative that This Is How My Life Is Now—even if we have wistful coulda should woulda moments—and lose sight that we still have the opportunity to course-correct those open-door regrets-in-the-making.

Regrets Prevention DepartmentI call them pre-grets. Corny cute, right? Regrets that are forming but not quite official yet—because the door remains open—regrets we could thwart with the right dose of courage to thwart them.

We can go back and learn that super-hard piano piece . . . before the door closes and we lose finger dexterity and/or our marbles.

We can ask our loved ones for forgiveness . . . before the door closes and our loved ones die.

We can establish a healthy relationship with our bodies . . . before the door closes and we end up with body dysmorphic disorder in the retirement home.

We can learn how to speak Italian . . . before the door closes and we’re too old/ tired/ poor/ lactose intolerant to travel to the Amalfi Coast.

As long as the door is still ~technically~ open, you can prevent a regret from taking hold of you. You are creative. You are courageous. You can figure out how to move to London if you want to. You can find a way to work with animals if you want to. You can find a way to be an artist if you want to. You can rearrange your childcare situation to get to take that bigger/ smaller job if you want to. If you have a heartbeat and a desire, you qualify to prevent a regret, my friend.

I urge you to NOT ARRIVE AT YOUR DEATHBED WITH PERFECTLY PREVENTABLE OPEN-DOOR REGRETS. You deserve to eat pistachio gelato in Positano . . . as long as I’m invited to visit.

Jodi Wellman

P.S.: I’d regret not asking you to buy 740 copies of my upcoming book, You Only Die Once: How to Make It to the End with No Regrets! (Or maybe just one copy.)

P.P.S.: Don’t regret not connecting with me on Instagram.

P.P.P.S.: Oh and just in case you missed it… I’d love you forever if you took 16 minutes out of your life to watch my TEDx talk!


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