Regrets

In the short run and the long run

Brave New World

September 1, 2025

Regrets in the short run and the long run

One may categorize regrets as arising from either: 1) an action taken with a less-than-desirable outcome; or 2) an action not taken that, later, you wish you had taken. That much is widely understood by most people. What is not widely understood, though, is how the variable of time affects the experience of regret and warps it in ways we can usefully predict.

Research (link) shows that in the short term, regretted actions do indeed cause more psychological pain than regretted inactions. But in the long run, it’s the other way around. For example, you may be familiar with the widespread belief that deathbed regrets (the long run) are more often about actions not taken. One healthcare worker, who worked with the elderly for more than a decade, summarizes: “I can’t speak for the young, but most often, old people regret the things they didn’t do.” (link)

In a conversation with my good friend John Boudreau (link), he proposed an explanation for this phenomenon: When we think about actions not taken, we picture them as the best possible ones. That trip to the Caribbean that you never took? The flights would have been on time, the beaches pristine, the fellow tourists few, and the weather beautiful, right? No bedbug infections, of course. In short, what we gave up—in our minds—by not acting was the perfect vacation. But of course, the reality, had that path been chosen, was likely to have fallen short of this ideal.

Note: I’m not claiming that we should not have regrets. However, I am claiming that regrets often are overstated in our minds, especially in terms of actions not taken. That said, a consistent theme in deathbed regrets is not spending more time with loved ones. Perhaps we can learn from that today and reduce our level of regret later.

Related to regret is an interesting psychological phenomenon that Mark Twain noted in his 1869 book, The Innocents Abroad:

"NEARLY one year has flown since this notable pilgrimage was ended; and as I sit here at home in San Francisco thinking, I am moved to confess that day by day the mass of my memories of the excursion have grown more and more pleasant as the disagreeable incidents of travel which encumbered them flitted one by one out of my mind…

Conjecture: the pain associated with “disagreeable incidents” is significant, perhaps because of loss aversion (link). Initially, Twain may have regretted going on the voyage. But our memories morph to reduce that pain, leaving us with a rosier recollection of an action taken and less regret.

How do these conjectures help us be happier and perhaps make better decisions? First, recognize that regret associated with inaction could well loom too large—it wouldn’t have been an ideal vacation, for example. Don’t beat yourself up too much for not having acted.

Second, the ubiquity of some regretted inactions nonetheless suggests that we should consider spending more time with loved ones and friends. As the saying goes, nobody ever said on their deathbed, “I wish I had spent more time at the office.” And socializing is well proven to be associated with greater levels of happiness and greater longevity. (link)

Our memories of actions taken may skew to the positive over time. Mark Twain, recalling his travels abroad, admits: “…if the [ship he sailed on] were weighing her anchor to sail away on the very same cruise again, nothing could gratify me more than to be a passenger.”

Dear Reader: Consider a regret you have now and see if you can accelerate its status to one of less regret or even a positive recollection. Feel free to report on how you did this. One possibility: reframing. (link)