On being a professor with regrets

Admitting that we wish we’d done things differently has come to be seen as a mark of spiritual immaturity. Perhaps as a reaction to the guilt-inducing traditional religions of childhood, many have adopted a policy of embracing whatever has occurred as a way of celebrating the present moment. While banishing regret may be fine as an absolute orientation towards the deepest meaning of life — on this view, what IS is good precisely because it is — on a mundane level, I think regret can be a useful ally.

Regret is especially relevant to me as a professor in this twixt time between the fall and spring terms. I look back on Fall with one eye as I look ahead to Spring with the other. The invitation to ruthlessly inspect my courses, to locate both the gems and dross, the tangled thickets and the open clearings, is too loud to be ignored. But still so close to the beauty and the wreckage of classes I’m just now completing, my vision is both sharpened and distorted. Learning to take a critical perspective on a past that is only just barely past demands that I move quickly away from defensive self-justification and make friends with regret.

Specifically, constructive regret requires that I be:

  • secure enough in my identity as a competent teacher that I can afford to have been mistaken about this or that; insecurity about my basic ability will lead me to defend and justify rather than honestly scrutinize;
  • invested not just in improving this or that particular skill or product, but in growing as a whole human being. Then, the motive towards general excellence can become habitual and irresistible; if I am satisfied with coasting dumbly along, either as a teacher, or as a moral, intellectual animal, then I won’t be motivated enough to make deep, lasting changes in any part of my life, including my teaching.

If I can make room for constructive regret in my teaching life — if I can see that that one assignment, the one I really loved, turned out to be a flop — then maybe I can also have a freer, more responsible relationship with the people and events that make up my whole life. If I can see failures — large and small — as messengers, and avoid identifying with them, then I can take better advantage of regret. Seeking and finding my own missteps and shortcomings — like consulting a map at a rest stop — can increasingly become a neutral habit rather than a shaming interlude that I avoid at all costs.

The pitfall of regret, then, is that it can so quickly become an implement for ruthless self-flagellation. One’s personal history and insecurities rise up so powerfully that the prospect of being vulnerable to self-examination becomes intolerable and so, instead, one moves fluidly into self-justification and rationalization. “I had to do it that way, because…” we tell ourselves, instead of authentically reflecting on the details of our motives or the consequences we set into motion. Rationalization becomes as automatic as a gag reflex, neutralizing the natural curiosity that would have us inspect and learn from our past.

There isn’t much that we do, whether in our classrooms or our larger lives, that absolutely had to be precisely the way it was. In most cases, we had viable alternative routes. Whether it’s about permitting a student to make up a quiz or speaking harshly to the person we love most, we can usually have done otherwise. And though we cannot, of course, know absolutely what the future would have been, our limited capacity to anticipate the consequences of our actions should, I think, sometimes lead us toward regret. How can we, I wonder, become more at home in the lively, tense knowledge that we could have, and perhaps should have, done it differently?

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