Why You’ll Regret Living a Life of Minimizing Regret

Focusing on regret minimization can, paradoxically, lead to regretful outcomes. Here's a different framework to consider.


No Regrets?

Last month I had a thought:

Maybe I could reposition The Zag as a go-to resource for finding ways to live with no regrets—or at least minimal regrets? And I could lead by example by pushing myself to live accordingly.

It seemed like a great idea…

Tattoo with no regrets misspelled as no regrats
Credit: We’re The Millers

Regret Is the Most Beneficial Negative Emotion?

Energized by my epiphany, I took to Google Scholar to research the science of regret and how to minimize it.

My first course of investigation:

The feeling of regret.

In one paper,1Saffrey C, Summerville A, Roese NJ. Praise for regret: People value regret above other negative emotions. Motiv Emot. 2008 Mar;32(1):46-54. doi: 10.1007/s11031-008-9082-4. PMID: 18535665; PMCID: PMC2413060. Colleen Saffrey and her colleagues compared regret to seven other negative emotions: anger, anxiety, boredom, disappointment, fear, guilt, jealousy, and sadness. They found regret to be:

  • The most painful negative emotion.
  • The second-most frequently felt negative emotion, after anxiety.

“This is great!” I thought. “Readers will flock to a blog and YouTube channel about minimizing the most abundantly excruciating negative emotion.”

But my enthusiasm didn’t last long. Because rather than admonish regret, the authors praised it for being far and away the most beneficial of the negative emotions.

People value their regrets substantially more than they value other negative emotions.

Praise for regret, Saffrey C, Summerville A, Roese NJ.

The study’s subjects valued regret “substantially” higher than any emotion for making sense of the past to provide insights that guide them toward avoiding repeating the same mistakes.

So regret is the mental equivalent of physical pain. And not just any pain, the worst pain. Burns, maybe?

People who feel nothing when they put their hand on a hot stove are cursed2The curse of the people who never feel pain, BBC Future to suffer clumsiness, disfigurement, and early death. Those who don’t feel regret likely face a similar fate, psychologically.

“Maybe,” I began to wonder, “a blog about minimizing regret isn’t such a good idea.”

What About Minimizing Regret in the Future?

Next, I read The Top Five Regrets of the Dying by Bronnie Ware.

The book’s about Ware’s experience as a hospice nurse for terminally ill rich people. If I were to tell her patients regret’s the most beneficial negative emotion, they would beg to differ. Understandably. Nobody wants regret souring the already dour scene at their deathbed.

So isn’t deathbed regret minimization a worthy objective?

It didn’t take much digging to find one super smart, ridiculously rich person who believes so:

Jeff Bezos, famous for founding Amazon and his regret minimization framework.
Photo by Steve Jurvetson

Jeff Bezos.

Seemingly every millennial with a Twitter feed, Medium profile, or Substack newsletter has preached about Bezos’ “Regret Minimization Framework.” When faced with tough decisions, the Amazon founder asks himself:

Toward the end of my life, will I regret not having done this?

I happen have a similar “framework,” my future self befriending mantra, WWFMD? (What would future me desire?) But, judging from the results, Bezos’ approach works better.

Either way, minimizing future regret seems like a good strategy. But regret’s also the most beneficial negative emotion. So what gives?

As usual, I found Daniel Kahneman had a clever answer.

Daniel Kahneman on using hot regret
Daniel Kahneman image from World Economic Forum

Split Regret Into Two

The deservingly famous psychologist suggests3Kahneman, D. (1995). Varieties of counterfactual thinking. In N. J. Roese & J. M. Olson (Eds.), What might have been: The social psychology of counterfactual thinking (pp. 375–396). Lawrence Erlbaum Associates, Inc. splitting regret into two separate feelings:

  • Hot regret. The painful but beneficial short-term reaction to an outcome that Saffrey et al. praise.
  • Wistful regret. The long-term, less-intense, sad fantasies of what might have been that Bezos and co. want to minimize.

The trick is to harness hot regret as a motivator to minimize wistful regret. And given that A) “Feeling is for doing”4Emotion, Motivation, and Decision Making: A Feeling-Is-for-Doing Approach, Intuition in Judgment and Decision Making, 2007 and B) Regret is the most painful feeling, this can get you doing a lot.

Another study I found supports this strategy.5Landman, J.T., Vandewater, E.A., Stewart, A.J., & Malley, J.E. (1995). Missed opportunities: Psychological ramifications of counterfactual thought in midlife women. Journal of Adult Development, 2, 87-97. It had women amp up regret by thinking about what might have been had they made better life choices. Doing so caused emotional distress in the short run, but led to motivational benefits in the long run.

You may even be able to harness imagined future regret to work toward your goals.

In a podcast episode on the science of setting and achieving goals, neuroscientist Andrew Huberman relays studies finding that foreshadowing failure—imagining the regret you will feel if you don’t work toward your goals—leads to more success than dreaming about the glorious feeling of success if you do the work.

Speaking of which, I began to foreshadow myself regretting acting on the idea of repositioning The Zag as being about avoiding regret. Better to have hot regrets—real and imagined—as fire under your butt.

But how do you keep that flame burning?

By making potentially regrettable decisions.

Regret expert Tom Gilovich
Thomas Gilovich in The Experience of Regret: What, When, and Why

Do Regret-able Things

According to Cornell’s regr-expert, Thomas Gilovich, errors made by action generate more regret than errors made by inaction.6Gilovich T, Medvec VH. The experience of regret: what, when, and why. Psychol Rev. 1995;102(2):379-395 This leads to “omission bias“—our tendency to favor sticking to the status quo over shaking things up.

For example, if I change this blog’s domain to DieRegretless.com and traffic tanks, I’d regret taking this action more than if I’d stayed put with TheZag.com and traffic tumbled all the same.

But here’s the catch:

Our regret of action over inaction is short-lived. In the long run, we feel the opposite. We regret inaction more than action.

Years from now, I may wistfully wonder whether changing this site to DieRegretless.com would have helped it take off. But I’ll know the answer if I make the change. Sure, I’ll regret doing so if it backfires, but I’ll also be able to revert back and patch it up psychologically with self-justification. My future self will be glad I tried and learned a lesson.

This insight led me to consider another Bezo-esque framework to spur myself toward “admission bias” over omission bias:

If you were doing it already, how likely would you go back to the status quo?

In my example of changing to DieRegretless.com…

…it’s highly likely I’d go back to TheZag.com, or maybe something else. “Die” is too harsh and serious.

But the lesson remains:

Default to taking action you might regret in the short term to minimize regret in the long term.

“We should focus less on making the right decisions and more on making sure our decisions turn out right.”

Ed Batista
Donald Miller advising to live a great story

You Won’t Regret Living a Good Story

“No one ever regrets taking the path that leads to a better story.”

Warren Berger, A More Beautiful Question,

Favoring action over inaction made me think of one of my favorite “sledgehammer” books that changed my thinking: Donald Miller’s A Million Miles in a Thousand Years.

It’s a memoir about how Miller learned to look at his life as a story and take control of the narrative to make it a good one.

Because, like it or not, you, Miller, and I are the heroes of our respective stories. But you won’t like it if you wait for a good story to happen to you. Cornell research finds that people’s single biggest regret in life is not fulfilling their ideal self.7Davidai, S., & Gilovich, T. (2018). The ideal road not taken: The self-discrepancies involved in people’s most enduring regrets. Emotion, 18(3), 439–452.

When asked to name their single biggest regret in life, 76 percent of participants mentioned a regret about not fulfilling their ideal self.

The ideal road not taken, Davidai, S., & Gilovich, T. (2018)

To be your best self requires taking action, making regrettable mistakes, and learning from them. In other words, it requires an inclination toward living a story worth telling.

Combining this with what I learned from my research about regret, I came away with this ultimate framework to guide my decisions:

Which action will lead to a better life story?

It’s also the direction I’ve decided to reposition The Zag toward. Rather than making it about living a life of no regrets, I want it to be about inspiring you to take action to lead an epic story-worthy life.

No No Regrets

Fittingly, my idea to make The Zag about minimizing regret was a mistake, but I’m glad I made it. It compelled me to do this deep dive and resurface with what I believe is a better approach. Worse comes to worst, I can always try something else.

Whether or not you agree with my anti-regret-minimization conclusion, I hope you don’t regret reading about how I arrived at it.

Even if you do regret it, use that to your benefit to drive you to take a better action next time. Ideally, a more story-worthy one.

Maybe these other posts of mine will help you figure out your next move:

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About the author

👋 I'm Chris. Everything you read on TheZag.com is my fault. This site is like a gym for your comfort zone, full of challenges to make your status quo sexier. Join my 'Consider This' newsletter for a fun new challenge every 10 days. Try it!

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