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February 3 - February 12, 2022
Our twin abilities to travel through time and to rewrite events power the regret process.
Comparison lives at regret’s core.
The only emotion mentioned more often than regret was love.
As she lay in bed, life about to slip from her battered forty-seven-year-old body, her final words were, “Every damn thing you do in this life you have to pay for.”
Every damn thing you do in life can pay off for you.
At Leasts deliver comfort and consolation. If Onlys, by contrast, make us feel worse.
One study found that 80 percent of the counterfactuals people generate are If Onlys. Other research puts the figure even higher.8 The main exception are situations in which we’ve eluded calamity.
At Least counterfactuals preserve our feelings in the moment, but they rarely enhance our decisions or performance in the future. If Only counterfactuals degrade our feelings now, but—and this is key—they can improve our lives later.
One study of CEOs found that encouraging business leaders to reflect on their regrets exerted a “positive influence on their future decisions.”
This is one of the central findings on regret: it can deepen persistence, which almost always elevates performance.
The near miss likely prompted regret, which spurred reflection, which revised strategy, which improved performance.
In fact, other research has found that people who thought counterfactually about pivotal moments in their life experienced greater meaning than people who thought explicitly about the meaning of those events. The indirect paths of If Only and At Least offered a faster route to meaning than the direct path of pondering meaning itself.
framing regret as a judgment of our underlying character—who we are—can be destructive. Framing it as an evaluation of a particular behavior in a particular situation—what we did—can be instructive.
When regret smothers, it can weigh us down. But when it pokes, it can lift us up.
Many of our education, finance, and health regrets are actually different outward expressions of the same core regret: our failure to be responsible, conscientious, or prudent.
Connection regrets arise any time we neglect the people who help establish our own sense of wholeness.
To identify a foundation regret in yourself or in others, listen for the words “too much”—whether they attach to consuming alcohol, playing video games, watching television, spending money, or any other activity whose immediate lure exceeds its lasting value. Then listen for the words “too little”—whether they describe studying in school, setting aside cash, practicing a sport or musical instrument, or any other undertaking that requires steady commitment.
the fix for foundation regrets, and a way to avoid them, is not only to change the person, but to reconfigure that person’s situation, setting, and environment.
Boldness regrets sound like this: If only I’d taken that risk.
Yet almost nobody in either the quantitative or qualitative regret surveys described excesses of extroversion, while many lamented tilting toward the other side of the scale.
their failure to be bold—with the same five words: “Not being true to myself.”
All deep structure regrets reveal a need and yield a lesson. With boldness regrets, the human need is growth—to expand as a person, to enjoy the richness of the world, to experience more than an ordinary life.
More than a hundred years ago, the French sociologist Émile Durkheim wrote that the defining feature of religious thought—and, I’d argue, many other belief systems—is “the division of the world into two domains, one containing all that is sacred and the other all that is profane.”10 We don’t always agree on the boundaries between those domains. But when we forsake what we believe is sacred for what we believe is profane, regret is the consequence.
People often talk about regrets in terms of doors. Amy has a “closed door” regret. As she told me, the opportunity to restore her connection with Deepa is gone. Cheryl has an “open door” regret. The opportunity to reconnect with her college friend remains.
regrets about social relationships are felt more deeply than other types of regrets because they threaten our sense of belonging. When our connections to others tatter or disintegrate, we suffer. And when it’s our fault, we suffer even more. “The need to belong,” they wrote, “is not just a fundamental human motive but a fundamental component of regret.”
What give our lives significance and satisfaction are meaningful relationships. But when those relationships come apart, whether by intent or inattention, what stands in the way of bringing them back together are feelings of awkwardness.
Push past the awkwardness and reach out.
That is the idea animating a theory of motivation that Tory Higgins, a Columbia University social psychologist, first proposed in 1987. Higgins argued that we all have an “actual self,” an “ideal self,” and an “ought self.”
For example, boldness regrets舒If only I’d taken that risk—are entirely about opportunities we didn’t seize.3 Foundation regrets—If only I’d done the work—are also largely about opportunities (for education, health, financial well-being) that we didn’t pursue. Connection regrets—If only I’d reached out—are a mix. They involve opportunities for friendship we didn’t follow through on, as well as obligations to family members and others that we neglected. Moral regrets—If only I’d done the right thing—are about obligations we didn’t meet.
Again, more opportunities could beget more regrets about unrealized opportunities.
When the universe of opportunities before them has dwindled (as it has with older folks), people seem to regret what they haven’t done.
But we can speculate that men, on average, may be more likely to value professional opportunities, and women, on average, may be more likely to value relationship opportunities.*
A life of obligation and no opportunity is crimped. A life of opportunity and no obligation is hollow. A life that fuses opportunity and obligation is true.
We’re more apt to repair what we did than what we didn’t do.
Apologies, wrote the great sociologist Erving Goffman, are “admissions of blameworthiness and regret for an undesirable event that allow actors to try to obtain a pardon from audiences.
The study, the researchers concluded, “provided both behavioral and neural evidence that self-disclosure is intrinsically rewarding.”
But unless carefully managed and contained, self-criticism can become a form of inner-directed virtue signaling. It projects toughness and ambition, but often leads to rumination and hopelessness instead of productive action.
“being imperfect, making mistakes, and encountering life difficulties is part of the shared human experience.”
The people who addressed their regret with self-compassion were more likely to change their behavior than those who approached their regret with self-esteem.
“People who self-distance focus less on recounting their experiences and more on reconstruing them in ways that provide insight and closure,”
“I watched a person let an important friendship drift. But all of us make mistakes, and she can redeem this one by reaching out to meaningful connections, including Jen, more regularly and more often.”
When we simulate looking at the problem retrospectively, from the binoculars of tomorrow rather than the magnifying glass of today, we’re more likely to replace self-justification with self-improvement.39
Looking backward can move us forward, but only if we do it right. The sequence of self-disclosure, self-compassion, and self-distancing offers a simple yet systematic way to transform regret into a powerful force for stability, achievement, and purpose.
Most maximizers were miserable.
Maximizers regretted everything at every stage. Before they made their choices. After they made their choices. While they made their choices. Whatever the situation, they always imagined the possibilities of something better if only they had acted differently.35 But these upward counterfactuals didn’t uncork productive “feeling is for thinking” regret. They trapped people in ruminating “feeling is for feeling” regret.
constantly trying to anticipate and minimize our regrets can become a form of unhealthy maximizing.
Call it the Regret Optimization Framework. This revised framework is built on four principles: In many circumstances, anticipating our regrets can lead to healthier behavior, smarter professional choices, and greater happiness. Yet when we anticipate our regrets, we frequently overestimate them, buying emotional insurance we don’t need and thereby distorting our decisions. And if we go too far—if we maximize on regret minimization—we can make our situation even worse. At the same time, people around the world consistently express the same four core regrets. These regrets endure. They reveal
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If our lives are the stories we tell ourselves, regret reminds us that we have a dual role. We are both the authors and the actors. We can shape the plot but not fully. We can toss aside the script but not always. We live at the intersection of free will and circumstance.

