The Point of Regret
- Ninay Desai
- 12 hours ago
- 4 min read
Most people have some regrets and a few learnings to go with them. Like a friend of mine who, when speaking of her relationship with her ex-husband, said she regretted not communicating better and understanding him as well as she could have.
Then, there are those who claim to have no regrets whatsoever. They usually go on to wax eloquent about how they are who they are as a result of their choices, before delivering a sermon about the moral benefits of practising acceptance. The only regret in such conversations is in your own heart for having asked them the question in the first place!
Jokes aside, regret is a miserable emotion wherein you blame yourself for an unfavourable outcome or a missed opportunity. Caught in a vortex of overthinking and self-recrimination, you wish you could undo a past choice, fantasising about how well things could’ve turned out. But regret isn’t always fair. Its finger always points at you, without exception. It places the blame at your doorstep for not knowing what only time and experience can teach.

THE PATH NOT TAKEN
At its core, regret is the emotion of unrealised possibilities. It doesn’t take the soaring imagination of JRR Tolkien to drum up ‘what if’ scenarios and alternative outcomes that appear better than your current state. You want to believe a different choice would have led to a happier outcome. If you didn’t think so, there would be no regret.
The sober side of your brain may attempt to remind you that life is a lot more complex and rarely pivoted on a single decision. But you ignore it. The reality of life’s interconnected dominoes may be more accurate, but it does little to soothe a regretful mind that longs for what might have been.
TYPES OF REGRET
Most regrets usually fall into one of these categories.
MISSED OPPORTUNITIES
Having a crack at something results in a definite answer, one way or the other. You either succeed or fail. Or fail miserably. But you never wonder ‘what if’. Not taking a chance when the opportunity presents itself is what many regrets are made of.
Slumped on your couch on a gloomy afternoon when your chips may be down, you regret rejecting the job offer from that start-up or not mending a friendship. People often regret inaction more than ‘crashing and burning’. Moreover, your experiments with failure have the added perk of transforming into life lessons or really hilarious stories!
TAKING THE SHORT CUT
Each of us have regrets revolving around an investment we didn’t make in the past which, had we done it, would have paid off handsomely. This is not limited to money.
I reckon many people regret not investing in their health over the years. They rue not joining a yoga class that met three times a week or continuing with their Spanish lessons.
FADED CONNECTIONS
Humans are social animals. That’s a cliché. It also happens to be true. Of all regrets, the ones that rankle the most are usually centred around relationships that slipped through your hands.
There are a variety of causes for faded connections—not keeping in touch, being too busy or a lack of honest communication. The reasons may vary but the result is often the same.
ERODING PERSONAL INTEGRITY
There may be times when you act in a manner out of sync with your personal values or the sort of person you want to be. Perhaps, you didn’t stand up to a boss who treated your unfairly or were less than straightforward with someone who trusted you.
Depending on how honest you are, you see what you did and regret sets in. You know you should have done better.
‘IF ONLY’ AND OTHER FANTASIES
Regret is an almost universal experience. Most of us have experienced loss and wished it wasn’t so. Daniel Kahneman, the Nobel Prize-winning psychologist, felt it too. He lost his nephew, Ilan.
Ilan was a 21-year-old navigator in the back of an Israeli fighter plane. In March 1975, he was killed when his pilot, blinded by a flare, flew upside down, straight into the ground. Ilan died five days before he was to be released from military service.
Even in his grief, Kahneman noticed how people mourning Ilan’s loss often started their sentences with “if only”. If only Ilan had been released from the Air Force a week earlier. If only he had taken charge after his pilot was blinded by the flare.
Kahneman understood that people cope with loss by drifting down fictional paths, where the loss never occurred.
WHAT MIGHT HAVE BEEN
The intensity of a regret, according to Daniel Kahneman, is a product of two variables: “the desirability of the alternative” and “the possibility of the alternative”.
I suppose that explains why the closer one was to a favourable outcome, the sadder and more regrettable things feel. When you think about it, ‘almost’ in certain contexts is such a sad word because it shows how close you came to having the object of your desire.
Regrets do have their uses though. They can help us see what we value as well as the error of our ways and hopefully, induce a change for the better. However, it is important to remember that the idealization of what might have been can also be a mirage, leading us aimlessly through a desert of pointless rumination.
As the Danish philosopher, Soren Kierkegaard said,
“Whatever you choose, you’ll regret it. Because the problem isn’t in your choices; it’s in romanticizing a life you haven’t lived.”
CONCLUSION
Can we minimise regret? My take is there’s no denying that other people’s actions as well as luck play a role in our lives. There’s precious little we can do about that.
The rest, however, is up to us. I recommend giving it your best shot. Maybe even a second shot. And then, as the song goes… Que sera, sera.



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