How to Relate to Your Worst Mistakes: The Life-Shaping Difference Between Regret and Remorse

You know it, that awful moment your coherent self-image shatters and a part of you, shadowy and untended, splits off to cause harm and havoc as the rest of you watches helplessly, wincing. You know the next moment, too — the desperate wish for an undo button you know cannot be had, no matter your protestations and prostrations. It is a seductive dream, to have an unregetting life, but it is also a dangerous dream, for it dooms us to the living nightmare of perfection, that punitive negation of our humanity.

If we didn’t shudder at our own missteps, we could never wish to leap higher. How achingly beautiful to be reminded that we are not cold algorithms whose very reason for being is to execute commands perfectly; that we are creatures whose imperfection is precisely what makes them perfect miracles of flesh and feeling. Our errors are the source-code of our self-transcendence.

Barring denial and dissociation, there are two ways to relate to our mistakes. Regret, rooted in rumination, is the desperate wish for an undo button — a wish that, however ardent, is hollow of consequence. Remorse, rooted in reflection, is the actionable desire for a redo — the drive, intentional and directional, to transform the revelations of reflection into a new working theory of doing better.

Regret is a turbine of self-destruction, remorse an engine of renewal. Drawing on the etymological and cultural heritage of both words, historian Tiffany Watt Smith offers a revelatory distinction between the two, both subtle and profound, in The Book of Human Emotions: An Encyclopedia of Feeling from Anger to Wanderlust (public library), which also gave us that wonderful lexicon of difficult emotions from around the world. She writes: The regret of the past was not the same as our won.

From the Old French regrés (sorrows or disappointments), when the word seems to have first entered the English language in the 1400s it described grief felt at the loss of a person, or one’s place in the world. One distinctive difference was that regret was also a kind of performance, an often-heightened expression of sorrow. The “making of regrets,” or regrettes, was a pious yet clamouring affair: the lamentations at a wake, the weeping at funerals.

In the sixteenth century — the moment historians associate with the birth of the modern concept of an interiorised self — regret began to harden into its contemporary meaning as a self-reproach, a private anguish felt looking back at some action you wish you’d not committed — or that you wish you had. It was at this time that the threat of this hidden torture, rather than punishment in the hereafter, became a deterrent favoured by parents and preachers alike. The real value of regret, Watt Smith observes, is to remind us of “the ambivalence which haunts all of our lives” — that disquieting evidence of the parts we live with.