Of all the things I fear (spiders, needles, people seeing my toes, rejection … the list goes on but I’ll spare you the gory details here), regrets are what strike the very most fear into my chickenhearted soul. I have a not-inconsequential sense of mortal dread about getting to the end and feeling ruefully disappointed—not so much by the life I lived, but by the life I didn’t live.\

At least I know I’m not alone. One of the modules in my online course is about regrets, and I hear from more participants in that section than almost any other, with poignant tales of the coulda, shoulda, woulda ilk. 

Regrets are 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. They aren’t always a bad thing, though; they can motivate us to change our behavior and better the circumstances of our lives. Mark Twain was spot on when he said 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). Here’s his pulse-quickening quote: “Twenty years from now you will be more disappointed by the things that you didn’t do than by the ones you did do. So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover.” This makes me almost willing to wear horizontal stripes and become a sailor.

Regrets based on inactions (like not taking that big job in Seattle, not starting that side hustle, or letting your secret high school flame become the one that got away) 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


What the Wisdom of Old Age Teaches Us About Regrets

Our eighth and final stage of being alive, according to Erikson’s stages of development, is known as the ego integrity versus despair stage—full of good stuff like seeking wisdom, feelings of fulfillment, and a sense of rocking-chair contentment. 

Erikson believed that despair was inevitable for those guilty about the past, looking back with the wistful belief that they didn’t reach the goals they had set forth or dreamed about. Studies show that hospice patients are often consumed by missed opportunities and perceived shortcomings, with little or no time to rectify the missteps on their near-term deathbeds. I guess it’s kind of hard to travel to Greece, go back for that graduate degree, or make amends with your brother when you’ve got one foot in the grave. 

Conversely, ego integrity (and maturity) is achieved for those with the conviction they’ve lived their lives well.


What Do We Regret the Most?

The Life Revision Index is a questionnaire designed to ascertain how retired people would spend their time if they had the chance to live their lives over again. Research finds that more than 70 percent of the study participants would have spent much more time pursuing their education, more than 60 percent would’ve spent more time doing things that brought them joy in life, and unsurprisingly, over 75 percent of the respondents said they’d have spent less time worrying about work if they had a life do-over. 

Proportionally speaking, here’s where our regrets sit (according to regret researchers, who really do exist):

  • Education: 32%
  • Career: 22%
  • Romance: 15%
  • Parenting: 10%
  • Self: 5.5%
  • Leisure: 2.6%
  • Finance: 2.5%
  • Family: 2.3%
  • Health: 1.5%
  • Friends: 1.4%
  • Spirituality: 1.3%
  • Community: .95%
  • Not eating more cheese: 22% (I made this one up, I know you know it’s true.)


Why Regrets Are So Valuable

Regret is actually the best of the worst; studies show we value regret substantially more than any of the negative emotions, perhaps because we innately grasp its functional value to help steer our decisions. (We value jealousy the least, in case you were curious.) This insight offers tremendous potential for how we opt to shape our lives. Anticipating regrets before they fully develop gives us a shot at a life we’ll feel proud to call our own. (Can I call them pre-grets and not sound embarrassingly corny?) (No? Okay. Got it.)

Thinking about our regrets-in-the-making, and course-correcting along the way to prevent them from manifesting—that’s a recipe for a well-lived life. You know what else is? Reflecting on our no-way-out-alive, inevitable death—because it forces us to be careful. Given that life isn’t long enough for a slew of do-overs, we’re best served to identify our most pressing wants and create a sense of urgency to take action on them. We risk getting to our end of days and facing the stark realization that we spent our time pursuing the wrong things, instead of the goals that might have given us a shot at even more joy. 

Bronnie Ware, author of the memoir The Top Five Regrets of the Dying writes that “most people had not honored even a half of their dreams and had to die knowing that it was due to choices they had made, or not made.” It’s this deathbed fear that prompted me to start Four Thousand Mondays; the idea of dying with a dream stuck inside me might have actually killed me.

You know what might kill you? Not knowing what Ware cited as the #1 regret in the palliative care patients she treated. Ready? These dying folks wished they had the courage to live the lives they wanted for themselves, not the lives others wanted for them. (I’ll just let that one simmer for a sec.) Might you regret living a life that’s designed to live up to someone else’s expectations? Might you shudder near the end for not living with integrity to what you really want for yourself? 


Using Regrets to Your Advantage

An unflinching awareness of your half-baked regrets (and of course your pending death, because everything leads to death, friend) can subtly shift you into a more vital state of being. Tapping into your potential regrets can even change the trajectory of your life. We’re not here to dwell on what you’ve already messed up (yeah, maybe you really should’ve asked Cindy to prom)—because all we have is now. We might not even have tomorrow! All you have is now and a bunch of regret-free choices to make until you’re six feet under.

What pangs of regrets do you already feel in your life? What paths have you yet to take that you know will lead to regret if you don’t reorient yourself? Cue this Turkish proverb here: “No matter how far you have gone on a wrong road, turn back.” Turn. Back. Today.

One more quote, or I know I’d regret it: “Of all sad words of mouth or pen, the saddest are these: it might have been.” —John Greenleaf Whittier

Go prevent a regret today. And eat more cheese.


Join Jodi on Thursday, October 20, at 12:00 pm for WBI/JCC Positivity Hour webinar, “Learning from Our Regrets to Boost Vitality and Meaning in Life.” Register here.


This post was reprinted from Jodi’s blog at fourthousandmondays.com.

Jodi Wellman

Jodi Wellman

Jodi Wellman is a speaker, coach, and facilitator on living lives worth living. She really just wants people to die happy—well, live happily and without regrets—while cleverly beginning with the “big end” in mind. With 17 years of corporate leadership experience, Jodi is a Certified Professional Co-Active Coach and an ICF Professional Certified Coach. She also completed the Positive Psychology Coaching Fundamentals course with Wholebeing Institute. Jodi has a Master’s of Applied Positive Psychology from the University of Pennsylvania, where she is also an Assistant Instructor. Learn more about Jodi and her work at fourthousandmondays.com.