Why You’ll Regret Living a Life of Minimizing Regret

In this post: How my research into regret minimization led me to conclude that anyone who pursues a life of “no regrets” will probably regret it.


Regret is as universally despised and undesired as root canals.

So last month I had a thought:

Maybe I could reposition The Unconventional Route 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

No Pain, No Gain

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 was into the feeling of regret.

In one paper, 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 of negative emotions.
  • The second-most frequently felt, 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.

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. The worst pain. Burns, maybe? People who feel no pain when they put their hand on a hot stove are cursed to suffer clumsiness, disfigurement, and early death. Those who don’t feel regret likely face a similar fate.

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

Kathryn Shulz speaking on stage about regret minimization
Kathryn Schulz, Don’t regret regret

Take Regret For a Ride

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

Ed Batista

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

It’s about her experience as a hospice nurse for terminally ill rich people. Her patients would beg to differ about regret being a beneficial negative emotion. 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 blabbered 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?

As it turns out, I have a similar “framework,” my future self befriending mantra, WWFMD? (What would future me desire?) But, judging from the results, Bezos’ approach seems to work 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

Thinking, Long and Short

The deservingly famous psychologist suggests splitting regret into two separate feelings:

  • Hot regret. The painful but beneficial short-term reaction to an outcome.
  • Wistful regret. Long-term, less-intense, sad fantasies of what might have been.

The trick is to harness hot regret as a motivator to minimize wistful regret. Given that A) “Feeling is for doing” and B) Regret’s the most painful of feelings, this can get you doing a lot.

Another study I found supports this strategy. 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 foresee myself regretting my idea of repositioning The Unconventional Route 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

Be Admission Biased

According to Cornell’s regr-expert, Thomas Gilovich, errors made by action generate more regret than errors made by inaction. 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 TheUnconventionalRoute.com and traffic tumbled all the same.

But there’s a catch:

Our regret of action more than 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. I’ll regret doing so if it backfires, but I’ll also be able to fix it. And 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 TheUnconventionalRoute.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.

Donald Miller advising to live a great story

Lead a Life Worth Telling

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

Warren Berger, A More Beautiful Question,

Favoring action over inaction brought to mind 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. To do so 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 Unconventional Route 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 Unconventional Route about minimizing regret was a mistake, but I’m glad I made it. It compelled me to do this deep dive and resurface with a different approach—a better one, hopefully. 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.

And 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.

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