Regrets: Your Secret to a Well-Lived Life

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 cause me the most fear in my heart. 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 module from 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. ilk. 

Regrets are a negative emotion that arises from our awareness. What could have happened 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. Get rid of the bowlines. The safe harbor is just a few steps away. Take advantage of the trade winds to your sails. Explore. Dream. Discover.” This makes it almost impossible for me to not wear horizontal stripes and be 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

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 are the Top 3 Things We Regret?

The Life Revision Index (or Life Revision Index) is a questionnaire that aims to determine how retired people would spend their retirement years if they could 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 important

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. (In case you were curious, jealousy is not something we value as highly as others. This insight opens up a world of possibilities for how we choose 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. It’s done.

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 the other thing 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 reaching the end of our days and realizing that the only thing we did was pursue the things we love. False things Instead of the goals that may have given us more joy, 

Bronnie Ware, the author of the memoir The Top Five Death Regrets 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 never know what could 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? Do you feel ashamed for not living the life you want? 


Refusing to accept defeats can be a great way to gain 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. You can change the course of your life by tapping into your regrets. 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 have tomorrow! All you have is now and a bunch of regret-free choices to make until you’re six feet under.

Are there any regrets you feel in your own 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

Today, don’t regret it. 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

Leave a Reply

Your email address will not be published. Required fields are marked *

Contact Us

Give us a call at (385) 312-0787  or fill in the form below and we will contact you. We endeavor to answer all inquiries within 24 hours on business days.

Error: Contact form not found.