I hate shopping for toothpaste. You probably know what I’m talking about. There’s the kind that’s good on cavities but doesn’t whiten. There’s the environmentally friendly brand that cleans well but doesn’t do much for the breath. There’s the all-in-one variety that looks promising but only comes in a small (expensive) tube. And then there’s every possible variation thereof. The hours I’ve killed in that brightly colored aisle are more than embarrassing, they’re borderline irresponsible.

Like you, I’ve read about the paradox of choice (the more options, the harder it is to choose), but truth be told, it has yet to make things any easier. When I’m standing there staring at the wall of options, I’m not searching my desires or my ridiculously limited knowledge of dentistry and mouthcare. I’m looking for the ‘right’ choice–which is far more complicated than the smartest, or cheapest, or healthiest one.

It would be less worrying (and tortuous) if there weren’t such a palpable corresponding fear of making the wrong choice, of being a person who makes bad and/or wasteful decisions, who gets taken in by the marketing machine… Of course, this is just the tip of the consumerist iceberg. The thought of buying the wrong car or house paralyzes on a whole different level. We’ll keep renting, thank you very much.

It sounds innocuous and silly–and it is. At least, it would be if the phenomenon were limited only to hygiene products. But it follows me wherever I go, whether it be saying the ‘right’ thing in any given situation, or making the ‘right’ use of my time, or following the ‘right’ career path, or choosing the ‘right’ mate, etc.

I’m not talking about status concerns or aesthetic concerns or happiness or even finances (although they are clearly interrelated). And I’m not saying that some choices aren’t wiser than others, that some decisions don’t carry moral weight. Obviously they do.

What interests/frustrates me here is how some of us invest more-or-less neutral decisions with a spiritual and moral significance they don’t possess. We turn life into a process of ‘getting it right’ (a problem to be solved) in which one of the chief things to be avoided is not loss or hurt but regret.

It’s not everyone’s deepest fear–others are more afraid of being rejected, or made to feel helpless, or hemmed in, etc–but it is certainly one of mine. This, even though I claim to know full well how illusory the underpinning mentality is, both in terms of the limits of ‘free will’ and the reality that even if the ‘right’ choice of socks or speaker cable or preschool exists today, it won’t tomorrow.

All this is a long-winded introduction to the best little essay I’ve read this year, “You’re Regretting Wrong” by Judith Shulevitz (my personal favorite columnist of last year), which appeared in The New Republic last month. She takes as her jumping off point the ‘public displays of regret’ which have become somewhat ubiquitous in recent years, often serving as a stand-in for an actual apology. Shulevitz is right – ‘regret’ is everywhere these days, and not by coincidence. She goes so far as to call it the “dark counterpart to American optimism”, ht ZW:

Public shows of regret come off as cringe-worthy because they fall short of apologies and stink of self-justification, but in fact they express a real emotion and reveal a plain truth. Regret is what we feel when we realize that we’ve hurt ourselves—damaged our careers, tarnished our reputations, limited our options. Regret is not remorse, which is what we feel when we’ve hurt others. Remorse—from the Latin mordere, to bite—implies the nip of conscience. It’s remorse that we want from our public figures after they misbehave, and remorse that they’ll almost never admit to…

People talk about “buyer’s remorse,” but the phrase gets it wrong. What I suffer from—and you do too—is buyer’s regret, because the bulk of our choices affect us more than other people. Buyer’s regret has much less moral import than buyer’s remorse but is more mortifying. If you do something to somebody, it’s awful, but there’s a chance that you can make amends. If you do something to yourself, you’re doomed to stew in gall for, well, however long you stew about such things.

Psychologists suspect that we regret more than we used to, because we make more choices than we used to. Economists spend a great deal of time nowadays trying to quantify both regret and “regret aversion,” because second thoughts, and the fear of having them, can have a volatile effect on markets. French novelist Michel Houellebecq likens our floundering in the face of proliferating goods and services to purgatory, “an endless wandering between eternally modified product lines.” So maybe the cold liberty of individual choice is God’s judgment upon our insatiable culture…

The connection with narcisscism and the key difference between regret and remorse are convicting (and undeniable), but the crux of the essay is what comes next (image via XKCD). In our parlance, Shulevitz locates ‘the law beneath the law’ and even hints at what Adam Phillips calls “the people we have failed to be”:

“Regret hurts because we venerate competence. Personal success is as much an American fetish as freedom of choice, so we feel duty-bound to make the kinds of decisions that lead to the best possible outcomes—to maximize our utility, as the economists say. If you subscribe to the cult of competence, it will feel like a bigger sin to sabotage yourself than others. The shame you suffer when caught doing something wrong will have less to do with having violated someone’s trust than with knowing you now look stupid or crazy…

I have come to see it as the lifelong tyranny of the counterfactual. I can never stop dreaming of what might have been, because it will always be better than what is. And this turns regret into a sort of existential tragicomedy. The regret I’m afraid of being pierced by, right here and now, traps me inside the farcicality of a detergent commercial. At some inadmissible level, I really do fear that buying the wrong product will lead to the wrong me—and so do you, because the brand-makers have always already outsmarted us both. But the regret we endure when we look back at everything we didn’t do, perhaps because we wasted so much time not being stupid, is the stuff of despair. In literature, it may also be the stuff of redemption. Think of Tolstoy’s Ivan Ilyich, who understands on his deathbed how meaningless his careerist life has been and is thereby freed to love. But that’s art, not life. Me, I’m already anticipating my future regrets, but that probably just means I’ll do nothing about them.

She is on to something major with Tolstoy, and it’s, er, regretful that she talks herself out of it. That is, Tolstoy’s truth, that the disillusionment brought on by death–or at least the death of illusions about ‘the right track’–can be the beginning of new life and redemption is not limited to literature, thank God. As any Lenten service worth its ashes will attest, regret can pass over into repentance–regret not merely of another blown opportunity for self-actualization in the toothpaste aisle, but of that persistent propensity to mess things up, to get it wrong.

I for one often do remain stuck running on the endless wheel of wanting to ‘get it right’ and regretting the times I didn’t. In the worst situations, those voices of doubt may move beyond irritating a touchy ego and instead dismantling it altogether – fortunately, that’s where Tolstoy’s true freedom, which is freedom from the very self that can regret, comes into play.

Some might say/pray that grace allows us to recognize those regrets for what they are – expressions not only of a tendency to err, but also of the pride that demands we get everything right. Cue the good news of original sin.

P.S. One can’t help but wonder if New Order regretted that choice of venue.

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