by Joshua Halberstam, philosopher, psyche.co

Edith Piaf sings ‘Non, je ne regrette rien,’ while Frank Sinatra does admit to a few regrets ‘but then again, too few to mention.’ Perhaps Piaf has a bad memory, and perhaps Sinatra would rather not remind us of his many regrets, but they both express a common view: regret is a waste of time. As Lady Macbeth, who ought to know about regret, insists: ‘Things without all remedy / Should be without regard. What’s done is done.’ You messed up? Get over it and move on.

This advice is not just unrealistic. It’s wrong. Approached honestly, regret is one of our clearest tools for seeing who we take ourselves to be.

Here’s an example from my own life. Music has always been one of my great pleasures and I have some musical talent. Not extraordinary talent, but some. While I don’t regret failing to become a professional pianist (that path far exceeded my capacities), I do regret the more modest failure of not having persisted long enough to master a Chopin nocturne. That regret stings precisely because it was a possibility commensurate with my abilities. Recognising my regrettable lack of discipline, I doubt I’ll pursue it even now.

There is, of course, the familiar concession: regret is acceptable if we learn from our mistakes. But this already sells regret short. It treats regret as a tool for course correction rather than as a source of self-knowledge. Presumably, once we’ve learned our lesson, regret is supposed to disappear. When it doesn’t (as is usually the case), we assume something has gone wrong. But these regrets persist not because we are neurotic, but because they serve a function we rarely recognise.

Regret, like other emotions, is both a feeling and a judgment. Unlike bodily states such as hunger or fatigue, emotions are directed at something. Fear is fear of a threat; anger is anger at someone. Regret, similarly, is directed toward a particular choice – an action taken or not taken – for which we see ourselves as responsible.

This element of responsibility matters. We often say ‘I’m sorry’ for events we didn’t cause – a natural disaster or a friend’s illness. But these aren’t regrets in the sense that concerns us here. Regret traces to human decisions. You cannot regret saying something cruel unless you believe you said it, just as you cannot be angry at someone for an insult you don’t believe they uttered.

The word regret covers a wide range of cases, from moral wrongdoing to everyday second-guessing. Philosophers sometimes specify a certain form of regret as ‘agent-regret’ – regret over outcomes we brought about, even when we are not morally at fault. Bernard Williams illustrated this with the example of a truck driver who, through no fault of his own, kills a child who runs into the street. The driver is not blameworthy, yet his regret is entirely intelligible. We expect apologies even for accidental harms.

Agent-regret spans both the moral and the mundane: the job not taken, the language not learned, the ill-advised purchase, the life-shaping decision. What unites them is not their moral weight but their connection to how we understand ourselves as agents – beings who accept responsibility for our lives when we acknowledge we could have acted differently.

Some regrets weigh on us; others do not. In my case, that unlearned nocturne still gnaws, but not every missed possibility does. The difference matters. As a child, I dreamed of becoming a baseball legend – the next Hank Aaron. But I don’t regret failing to become a Hall of Famer. That life was never genuinely available to me. I lacked both the requisite abilities and the opportunity, and I no longer prefer that imagined life to the one I have. That counterfactual simply doesn’t resonate.

But some failures do resonate. The list of achievements I could have realistically pursued is long: I could have learned Spanish, spent more time in foreign countries, kept up with old friends. This distinction between fantasy lives and realistic alternatives explains why missing a flight by five minutes feels worse than missing it by three hours and why losing the lottery by one number is more painful than losing by seven. The world needed to be only slightly different for things to have gone well. The alternate reality feels uncomfortably close.

Thoughtful regret reveals not just what we wish had gone differently, but which unrealised possibilities still feel like ours. This is the regretting that can illuminate our values, our self-conception, and how we estimate our potentials and limits.

To see how regret serves as a diagnostic, it’s useful to compare it with its cousin: envy. Few envy Jeff Bezos his billions or Tom Brady his athletic gift because those achievements fall outside the perceived range of realistic possibilities. But envying a colleague’s success or a friend’s diligence is much easier since similar achievements are all too conceivable. Envy, therefore, reveals where we locate ourselves relative to others in domains that matter to us.

Regret provides a similar kind of insight. By revealing which alternatives felt genuinely possible, it presents a clearer self-image – one that is often blurred. Both emotions are uncomfortable for the same reason: they expose what is taken to have been possible. Envy can be softened by shifting social groups or dwelling on others’ flaws, and regret is blunted by imagining the different regrets we’d have faced had we chosen differently. These manoeuvres reduce discomfort, but they also obscure honest self-assessment.

The diagnostic value of regret, however, depends on what we’re actually regretting. Not all regrets illuminate equally. Do people regret more what they did do and shouldn’t have, or what they didn’t do but should have? It depends. In the short term, regret is strongest for things we did – the thoughtless comment, the impulsive purchase. That’s because, as Daniel Kahneman and Amos Tversky showed, actions are easier to mentally ‘undo’, which makes the regret sharper in the moment. But, over time, we regret more what we didn’t do – a finding that goes back to work by Thomas Gilovich and Victoria Medvec. Misguided actions sting sharply but fade; failures to act grow heavier with time. Looking back at our lives, it’s those omissions we most regret – the relationship not pursued, the opportunity we let slip away.

This helps explain why ‘deathbed wisdom’ is so popular. The appeal of listening to the dying is that they supposedly possess a special honesty and clarity in looking back on their lives. But we should be wary of drawing conclusions from these accounts. First, there’s limited rigorous research on what people actually say right before they die. Second, there’s no reason to privilege deathbed regrets, which might reflect a person’s current state of mind more than the misgivings they have carried through life. We’re all subject to hindsight bias – judging past decisions as obvious in retrospect, though they weren’t clear at the time. At the end of life, one might wish they’d worked fewer hours even if it meant earning less money, but hard work might have made good sense given what one knew then. We don’t necessarily become wiser just because our life is ending.

Nonetheless, there is an important insight in end-of-life reflections: the shift of focus from actions to dispositions. In their final hours, people don’t regret a missed flight or a badly played game of poker. Instead, they regret their persistent traits – the grudges they harboured for decades, the stubbornness that ended a friendship. And this recognition points to a largely ignored dimension of regret: we don’t just regret what we did, we regret who we allowed ourselves to become.

Most discussions of regret focus on actions. But deeper regrets concern character. Think of those people who are perpetually angry or who habitually blame others – these traits shape lives more powerfully than any single decision. And yet, they receive far less attention when we talk of regrets.

There are several reasons for this. Actions are clear cut and easy to identify: we know what we did or didn’t do, while personality traits are more amorphous. But the main reason we neglect regrets about our character is that traits feel less voluntary. We didn’t choose our parents, our height, or our genetic endowments, and character traits – laziness, say, or timidity – are often thought of as similarly fixed. But, as Aristotle insisted long ago, and robust evidence now shows, our traits can change over time and we can intentionally make those changes. When we should have and didn’t, we have much to regret.

Confronting personality flaws is uncomfortable, so it’s tempting to avoid. Research shows people are often better at recognising traits when they’re obvious to others and lack serious moral implications. Most people know whether they’re talkative or introverted but are less likely to admit to negative traits like stubbornness or mean-spiritedness. When confronted with a serious flaw, the easiest defence is often a shrug: ‘That’s just who I am.’

But that shrug is a choice. In her influential work on motivation, Mindset: The New Psychology of Success (2006), Carol Dweck distinguishes between a fixed mindset – the belief that abilities are static – and a growth mindset, in which failures become opportunities for improvement. Character traits are, similarly, shaped by our assumptions about them – and assumptions can change. Regret, properly heeded, can show us exactly where to begin to make those changes.

The underlying truth here is that the lives we didn’t live aren’t mere outtakes; they are part of the narrative structure of our actual, ongoing life. By examining closely what we truly regret – the particular actions we did or didn’t take, as well as the unpleasant traits that contour our lives – we gain a richer understanding of our self-conception. To be sure, some of what we discover we will have to accept. But some of our regrets will point toward new possibilities – and the possibilities that haunt us reveal more about who we are than our successes ever could. Perhaps I can still learn that nocturne after all.

Joshua Halberstam teach­es philosophy and Judaic studies at CCNY of the City University of New York. He received his doc­tor­ate in phi­los­o­phy from New York University while pur­su­ing postgrad­u­ate Tal­mu­dic stud­ies.

Keywords; decision-making, psychology