Ready to play the always-riveting game called “Imagining Your Deathbed Regrets”? Of course you are—there’s no place for surface-level froth here at the Wisdom Well blog, right? No, friend, we’re going deep! Not quite six-feet deep, but close.

So here you are on your imaginary deathbed, and from this one-foot-in-the-grave vantage point, reflect on the years you’ve been lucky to live. You’re probably proud of some things, and if you’re like 82.4% of us, you’d like a re-do on a few things, please and thanks.

Regrets can motivate us to change our behavior and better the circumstances of our lives. Defined as the negative emotion born from our awareness of what could have been if we’d only made a different decision with the benefit of 20/20 hindsight, Mark Twain was spot-on that we’re more likely to regret the things we didn’t do than the things we did (and just wish we did so much better, with way better hair).

Regrets based on inactions (like not starting that side hustle, not going after that big job in Portland, not studying anthropology, or not saying yes to Ralphie’s prom invitation) tend to haunt us, mostly because these paths not taken represent gaps between our actual selves and what we’ve envisioned as our ideal selves (the versions that have their shit together and makes hopes and dreams and goals come true).

‍Researchers are clear that these “paths not taken” can 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.)

From the pleasantly sedated comfort of your imaginary deathbed, what pangs of regret do you feel about your paths not taken? What choices and dreams and notions and hobbies and travels and conversations and adventures and courses and goals and Big Life Changes and Small Life Tweaks might you feel the “Coulda Shoulda Woulda” cringe about not doing? If your hospice care worker was kindly taking notes for you, what would they write in your Compendium of Lost and Unfulfilled Dreams?

This is your list of what I call pre-grets—regrets-in-the-making that aren’t quite official yet—regrets you could thwart with the right dose of courage to thwart them, because as long as you are not on your deathbed, there is still time to do the thwarting.
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As George Eliot said, “It’s never too late to be what you might have been.” 

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 at a not-for-profit if you want to. 

You can have gelato on the Spanish Steps in Rome if you want to. 

You can open an Etsy shop 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 regrets (especially if they involve gelato). So since you’re likely not within an inch of your life, what pre-gret will you thwart today?

-Jodi

Jodi Wellman is a speaker, author, assistant instructor in the Master of Applied Positive Psychology program at the University of Pennsylvania, and founder of Four Thousand Mondays. She really just wants people to live squander-free lives while they’re lucky to be alive. Her book, "You Only Die Once: How to Make It to the End with No Regrets" will be published in May 2024 by Voracious (Little, Brown & Company).