Elul 2023

 I came across an interesting article in the paper the other day. Written by Jancee Dunn, a NY Times columnist who writes for the “Well” newsletter available to Times subscribers, the article was about the concept of regret and specifically what two authorities in the field had to recommend as ways to deal with it. So that was a surprise: who even knew there were experts in the study of regret? I couldn’t have named any, but Jancee Dunn knows at least two: Robin Kowalski, a professor of psychology at Clemson University in South Carolina who studies the topic scientifically, and Daniel H. Pink, once a speechwriter for Al Gore but now the author of a series of a specific kind of bestselling book including Drive: The Surprising Truth about What Motivates Us (2009),When: The Scientific Secrets of Perfect Timing (2018), and now The Power of Regret: How Looking Backward Moves Us Forward.

So that got my attention. Elul, the month preceding the High Holiday season, is all about regret. Or maybe not about regret per se, but about introspection, self-analysis, and the honest consideration of the year about to conclude with an eye towards resolving how to live better and/or finer lives in the year about to begin.  And I suppose it is probably inevitable that that kind of self-scrutiny will lead to at least some version of regret: which of us has never spoken a word in haste that we regretting immediately having uttered or made a decision that felt reasonable at the time but that we subsequently saw as a huge error of judgment? So, yes, regret is part of Elul. Other than for true tzaddikim, how could it not be? And even the truly righteous in our midst speak the occasional word in haste: the difference between the tzaddik and the rest of everybody is not that the former is perfect and the latter, imperfect, but that the truly righteous have the inner courage to own up to their errors and miscalculations, to make them right as best they can without blaming the victims of their own poor judgment, and to learn from them. Therefore, regret is the perfect topic for Elul.

Pink, a graduate of Yale Law School, conducted an interesting survey to provide the data that he then interpreted in his book and the results of that survey are available on line (click here). And the results, featuring the responses of almost 4500 American respondents, are fascinating. Fascinating, but also a bit contradictory.

More than half (53.7%) of the people polled, for example, responded that it was either extremely, somewhat, or slightly harmful to think about one’s regrets at all!  And yet, when asked if they ever look back on their lives and wish they had done something differently either rarely, occasionally, frequently, or constantly, a full 98.9% responded that they had done just that and a mere 1.1% reported never having done so. So that’s interesting: only about half of the people who admitted to looking back on their lives and wishing they had done something differently considered that to be a salutary, positive exercise!

In another interesting disconnect, when asked if they thought that things in life happen “for a reason,” a full 78.7% responded positively (i.e., that they do think that) and another 10.5% answered that they considered that to constitute a distinct possibility. So that would be almost 90% of the respondents who considered it at least possible that things happen for a reason—which is to say that human beings are not fully autonomous beings, but rather, at least to some extent, the victims (or the beneficiaries) of fate, of kismet, of predetermined destiny. And yet when asked if they believed in free will (that is to say, if they believe people to be completely free to chart their courses forward in life and to live with the consequences of their own decisions), an amazing 93.8% of the respondents considered that to be a self-evident truth or at least possibly to be the case.

Taking both these sets of contradictory data into account, then, I conclude that people do regret things in life—but they are not sure they are acting in their own best interests by doing so…and they are more than ready to entertain the possibility that they weren’t fully responsible for the things they regret. Neither of these thoughts could possibly be less in sync with the lessons of Elul.

And then there’s the question of what to do about the things one regrets in life? That was the question Jancee Dunn posed and asked Robin Kowalski and Daniel Pink to answer. It’s a good question! And they came up with three specific answers to it.  All were resonant with me, yet something crucial seemed to be lacking. First, their three suggestions.

The first is to be forgiving of yourself, and no less so than you would be of a friend who came to you bearing the same burden and asking for your counsel. This, at least to me, sounds a bit self-serving: you’re regretful and unhappy, and the solution they offer is to tell yourself that your regrets and your unhappiness don’t make you a bad person. That does not sound especially consoling, or at least to me it doesn’t. And, besides, why would anything think in the first place that only bad people harbor regrets about this or that incident or decision in their past?

The second suggestion is to address the issue from a practical standpoint by asking if there is some way you can undo what you have done, if you can defang your regrets by actually undoing the decision you have come to rue. Sometimes, this will be quite possible. (You can transfer schools, change jobs, switch banks, etc.) But there are surely times when it isn’t that simple to undo an earlier decision or even impossible to do so. But neither author has a clear plan for such instances.

And the third is to reframe the issue under consideration by undertaking what Pink calls “at-leasting,” the technique in which you make yourself feel less regretful by focusing your thoughts on the matter through the “at-least” portal: I wish I had followed my heart and become a teacher, but at least I’ve made a lot of money as a brain surgeon. This one also strikes me as at least slightly cowardly: dealing with regret by convincing yourself that you could have made an even worse decision than the one you did make—that does not seem to me at all like a courageous path to take or a very satisfying one.

Missing from all the above, however, is anything approximating the rabbinic concept of t’shuvah, of repentance as opposed to remorse or mere regret. In the section of his masterwork devoted to the laws of repentance, for example, Maimonides devotes several chapters to outlining the specific ways in which one can sacralize regret—if one can say such a thing—by transforming regret from mere remorse into a channel for spiritual growth.

First, he writes, you need to focus your thoughts so fully on the specific thing you now regret that you feel transformed or even ennobled by the experience of honest self-scrutiny rather than merely wracked with guilt in its regard. In other words, regret can be elevating rather than devastating when it serves as a marker on the road towards spiritual elevation and growth. The scientists quoted in the article suggested that this could (and maybe even should) be an internal process, but that is not how Jewish tradition sees it at all: for t’shuvah to be meaningful, it has to be undertaken in public. You need formally to give voice to your regrets. And then you need to act on them.

And acting on them means taking conscious steps to undo them. Sometimes, this is simple: if you regret stealing something, you can obviously just return it. But other times this is impossible or almost impossible. If, for example, the person to whom you must make amends has died, Rambam instructs you to gather a minyan at that person’s grave and there explain aloud what specifically you regret. If you owe the deceased person money, you should return it to his or her heirs. If you can’t locate any heirs, you should deposit the full sum with the local beit-din and leave it there until an heir materializes. The point here is not who gets to keep the money, or not solely that, but whether you can harness the regret you know feel about having done something wrong that cannot be undone simply (or at all) and allow it to draw you forward into a better version of yourself.

The scholars cited in the paper seemed to assume that regret was somehow toxic—or at the very least unhealthy—and is therefore something to work through and get rid of.   The Jewish approach—the Elul option—is to harness the energy generated by regret and to allow it to draw you forward into becoming a finer version of yourself. To regret things is part of human life; surely, no one manages to get through life without making at least some poor decisions! The question is whether you see regret as something to be identified so that it can be jettisoned as quickly and completely as possible…or as something to be embraced and nurtured as a worthy engine for internal growth. Facing regret square on and allowing it to mold your character positively—that is what Elul is all about.