"I regret everything. Decades-old decisions, things I said, things I didn’t say, opportunities I missed, opportunities I took, recent purchases, non-purchases, returns. I turn all of these things over in my mind and examine them for clues — to what, I’m not sure. All I know is that very little of what I do or fail to do escapes the constant churn of revision. It’s just the way I process experience: sceptically, and in retrospect. It’s like being a time-traveller, only instead of going back to Ancient Rome or the French Revolution, I return again and again to the traumatic sites of my own fateful (or not so fateful) forks in the road. Some people see this as self‑flagellation; I tend to think of it as a lifelong effort to reconcile the possible with the actual — a getting to know the real me. After all, as they say, we’re defined by our choices. …
There’s a particular disdain for regret in US culture. It’s regarded as self-indulgent and irrational — a ‘useless’ feeling. We prefer utilitarian emotions, those we can use as vehicles for transformation, and closure. ‘Dwelling’, we tend to agree, gets you nowhere. It just leads you around in circles.
Regret is so counter to the pioneer spirit — with its belief in blinkered perseverance, and dogged forward motion — it’s practically un-American. In the US, you keep your squint firmly planted on the horizon and put one foot in front of the other. There’s something suspiciously female, possibly French, about any morbid interiority.
Best, then, to treat the past like an overflowing closet: just shut the door and walk away. ‘What’s done is done,’ we say. ‘It is what it is.’ ‘There’s no use crying over spilt milk.’
Sometimes, the prevalence of this point of view makes me feel regret toward my tendency toward regret. It’s hard not to feel bad when your way of processing experience is routinely pathologised, or dismissed offhand as whiny, weak, and useless. As I write this, I regret writing it because I fear it makes me sound more neurotic than I really am. At the same time, I worry that it makes me sound exactly as neurotic as I actually am, and I regret not having done a better job of keeping this under wraps. I regret regretting things all the time, because surely I could be putting my imagination to better use. What’s more, I regret that I’m compelled to talk about my regrets, not just in therapy, but at dinner, at the playground, on the phone, and in print. I regret these things in part because I’m acutely aware of how my regrets are perceived when I express them. What I want are deep explorations of parallel universes and alternative outcomes. But what I get in return are sad-eyed smiles, gentle pats on the arm, and the occasional rousing pep talk, which is never what I’m after.
The assumption is that these ruminations stem from a flaw in my character, or an unresolved trauma, or some questionable behaviourist conditioning. It’s a neurobiological glitch, maybe, or a bad habit. And all of these might apply, but I also think I’m driven by a combination of pragmatism and curiosity. Whenever I come up against a problem, or find myself plagued by questions I can’t answer, my impulse is to lift up the hood of my day-to-day denial and complacency and dive into the intricate circuitry of my past in search of whatever minor gasket malfunction sparked the powder train that eventually blew up the spacecraft. I guess in some way, I’ve come to think of regret as a deductive game that, although it’s almost never fun, will eventually unlock all of life’s mysteries. Is this what I intended to do? Could I have predicted this outcome? How did I get here?”
Read on: Why Regret is Essential to the Good Life