How to Live With Less Regret
Regret is painful, but it is also a guide to what matters most in life
Well-meaning people sometimes offer the following advice: “Don’t do something you will regret!” If you smoke cigarettes, you might get lung cancer, and you will regret that—so don’t smoke. If you have an affair, your partner might leave you, and you will regret that—so don’t have an affair. It seems sensible enough.
On consideration, however, this advice is not as clear as it seems to be. The philosopher Lloyd Humberstone observes that this advice, if taken literally, will often lead us astray.
Humberstone, in his article, “You’ll Regret It,” asks us to consider horse racing. I might reasonably bet $2 on a horse to win. If it wins, I will regret betting $2—I will wish I had bet more. If it loses, I will regret betting $2—I will wish I had bet nothing. I know I will regret betting $2, no matter what. Yet it can be (sometimes) reasonable to bet.
Once we notice Humberstone’s point, we see it everywhere. We choose a vacation or a college under conditions of imperfect information and we can be pretty sure that, when we reach the future and know more, we will look back and see what we should have done instead. In this way, regret feels pretty much inevitable.
In addition to this regret based on shifting information—what philosophers call epistemic regret—there is also regret based on our changeable sense of goodness, or what philosophers call evaluative regret. We may look back at our life choices and notice all their lamentable features, ones which we did not notice at the time, or even once regarded as good. We might choose a career based on the opportunities for travel, and then, years later, regret all our time spent far away from home.
As almost every choice has some bad aspect or other, evaluative regret is always available. Both a choice and its opposite can each have downsides that, when we attend to them, can make them seem obviously regrettable. It is perhaps this phenomenon that Kierkegaard had in mind when he wrote: “Marry, and you will regret it; don’t marry, you will also regret it; marry or don’t marry, you will regret it either way.”
It is this pervasive aspect of evaluative regret that may explain why severe depression, with its upending of all sense of what is good, is often marked by pervasive and all-consuming depression. But the distinctive melancholy of evaluative regret can be present even in moods of equanimity, and it is familiar, in one mode or other, to almost everyone.
If this is right—if regret, given our ignorance and shifting values, is inevitable for almost all of us—then the advice to simply avoid is advice that imperfect beings like ourselves simply cannot follow. Should we simply then disregard regret as an emotional inevitability?
What Regret Can Teach Us
Regret may be inevitable, but we should not ignore it. For regret has something to teach us, and the avoidance of regret may be a good goal—even if it is a goal that we can never quite reach. To understand why, it is helpful to look at psychological studies of the circumstances under which people actually feel regret.
The psychologist Thomas Gilovich and his co-authors have conducted revealing studies of the actual dynamics of regret: that is, what we regret, and why, and how regret evolves over time. Two of Gilovich’s results are especially striking.
The first, identified in work with Victoria Husted Medvec, is the difference between action and inaction. In the short run, people are inclined to regret the things they do. This is the uncomfortable feeling one gets immediately after realizing one has gotten off at the wrong exit or made a thoughtless remark.
But, in the long term, it is the things that they don’t do that people most regret. At the top of people’s most common regrets are not pursuing more education, not spending enough time with friends and family, and missing romantic opportunities. In the long run, it is our inactions, rather than our actions, that we most regret.
The second, identified in work with Shai Davidai, is that people’s regrets arise most often from “discrepancies between their actual and ideal selves.” That is, we tend to regret our failures to do things that would have fit our ideals of what we want for our lives to look like, our aspirations for ourselves. Someone whose lifelong dream is to be a doctor but who decides not to apply to medical school may be prone to a deep and persisting regret over their failure to pursue their aspirations.
In contrast, we are less prone to regret our failures to do what we think we ought to do, according to general standards. Someone whose parents want them to be a doctor, and who perhaps agrees that that is a good career, may nonetheless not be prone to regret that our decisions. It is our own expectations for ourselves, and not other people’s, that are the ultimate sources of regret.
If this is right, then regret tends to be driven by our failures to live up to our own ideals. This does not make regret any easier to live with—in fact, it may make it much harder. But it does make its significance clearer. Life is filled with countless pressures towards inaction and neglect of our own aspirations, towards cowardice and conformity. Regret can pull us away from these inertial forces, or at least let us know when we have given in to them.
The advice to avoid regret, then, is advice that we cannot fully follow. Some measure of regret is inevitable. Nonetheless, it may be good advice. For it encourages us to act rather than refrain, and to follow our own goals rather than conventional expectations. And those are things that are well worth doing.