All deep structure regrets reveal a need and yield a lesson. With connection regrets, the human need is love. Not love only in the romantic sense—but a broader version of love that includes attachment, devotion, and community and that encompasses parents, children, siblings, and friends.
The lesson of closed doors is to do better next time. The lesson of open doors is to do something now. If a relationship you care about has come undone, place the call. Make that visit. Say what you feel. Push past the awkwardness and reach out.
“My biggest regrets stem from not being more assertive at various life points about my needs and wishes—education, relationships, vacation plans, right down to the food that winds up in my house.”
Male, 51, New Jersey
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“I wish I had planted more trees.”
Male, 57, United Kingdom
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“I regret putting my life on display for so long on social media. There are too many times I overshared and now it feels like too much of me is just ‘out there.’？”
Female, 27, Washington
11.
Opportunity and Obligation
Photography was more complicated and expensive back in the twentieth century before every phone had a camera and every pocket had a phone. Gather round, youngsters, and I’ll explain.
In those bygone days, photographers shot their photos on film. They’d press a button to open their camera’s shutter, which would momentarily let in light. The light would then interact with chemicals on the film to memorialize an image.
The result was a bit odd. On the strip of film that photographers removed from the camera, the light spots appeared dark and the dark spots light. This was called a “negative”—and it was the middle step in the production process. When photographers printed that negative on paper, the light and dark would be reversed and the original color tones restored.
Regret works much the same way. The four core regrets operate as a photographic negative of the good life. If we know what people regret the most, we can reverse that image to reveal what they value the most.
So, what do we all ultimately want and need?
The deep structure of regret, summarized in the table below, provides an answer.
THE DEEP STRUCTURE OF REGRET
We seek a measure of stability—a reasonably sturdy foundation of material, physical, and mental well-being.
We hope to use some of our limited time to explore and grow—by pursuing novelty and being bold.
We aspire to do the right thing—to be, and to be seen as, good people who honor our moral commitments.
We yearn to connect with others—to forge friendships and family relationships bonded by love.
A solid foundation. A little boldness. Basic morality. Meaningful connections. The negative emotion of regret reveals the positive path for living.
COULDA AND SHOULDA
Each time you look in the mirror, you see one person. But if you squint a little harder, you might see three selves.
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.”
Our actual self is the bundle of attributes that we currently possess. Our ideal self is the self we believe we could be—our hopes, wishes, and dreams. And our ought self is the self we believe we should be—our duties, commitments, and responsibilities.[1]
What fuels our behavior and directs which goals we pursue, Higgins argued, are discrepancies between these three selves. For instance, if my ideal self is someone who’s healthy and physically fit but my actual self is lethargic and overweight, that gap might motivate me to start exercising. If my ought self believes in caring for elderly relatives but my actual self hasn’t visited Grandma in six months, I might leave the office early and to Grandmother’s house I will go. However, when we don’t make these efforts, when a discrepancy persists between who we are and who we could or should be, unpleasant feelings flood the gap.
In 2018, Shai Davidai, of the New School for Social Research, and the ubiquitous Thomas Gilovich enlisted Higgins’s theory to analyze regret. Expanding on Gilovich’s earlier research showing that, over time, people regret inactions more than actions, they conducted six studies that reached a single conclusion: people regret their failures to live up to their ideal selves more than their failures to live up to their ought selves. Regrets of “coulda” outnumbered regrets of “shoulda” by about three to one.
The likely reason is the contrasting emotional consequences of these two flavors of regret. Discrepancies between our actual self and our ideal self leave us dejected. But discrepancies between our actual self and our ought self make us agitated—and therefore more likely to act. We feel a greater sense of urgency about ought-related regrets, so we’re more likely to begin repair work—by undoing past behavior, apologizing to those we’ve wronged, or learning from our mistakes.[2] “Couldas” bug us longer than “shouldas,” because we end up fixing many of the “shouldas.”[*]