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. “For this deed thou shalt for anguish fret,” warned the Calvinist parliamentarian Francis Rous in 1598 and “feed thy wombe with woe and deepe regret.”

Today, regret remains firmly entrenched as a private emotional experience… The regrets we feel most sorely are often the ones that jar hardest with our sense of self.

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.

But because regret is at bottom “a kind of desire for something different to have happened,” it is an emotion shot dead by time’s arrow. Hannah Arendt knew this when she considered the only antidote to the irreversibility of life — not regret but redemptive action.

The fulcrum of such action, Watt Smith argues, is remorse. With an eye to the scorching self-blame we feel when we first recognize our harmful missteps, she writes:

Remorse arrives when the initial flare of anger calms, when the reality of what we’ve said or done clumps in the throat. Unlike the whirring and suffocation of regret, remorse is urgent and wild. Full of terror, flecked with love, it’s a desire to preserve our bond with the person we’ve hurt… Remorse, then, is most clearly defined as an urgent desire to do something. To make amends, to attempt to heal the one we’ve harmed. Because, unlike shame, which is a horror of something we are, remorse involves something done, and urges us to correct it. In this sense, remorse is both extremely painful and full of striving and hopefulness too.

Remorse, however, is haunted by the specter of regret, which is inherently an act of selfing — a spiral of rumination borrowing into the substrate of our deepest self-doubt. “Excessive remorse,” Watt Smith cautions, may “lead to disproportionate acts, causing more grief, rather than less” — a haunting reminder that our morality hinges on unselfing, and the purpose of reflecting on our errors is not to allay our self-blame but to effect repair and healing for those we have harmed, the catalyst for which is correctly calibrated remorse.

Couple with dissident poet turned president Václav Havel, writing from prison, on how to hold your greatest failure, then revisit Ellen Bass’s benediction of a poem “How to Apologize.”