Last night, Dena Weiss of Hadar gave a class at Harvard Hillel in preparation for the High Holidays. We took a look at Talmudic sources that could illuminate questions of how much atonement is the right amount, when it’s better to make apology and move on, what it means to see the same items on your cheshbon hanefesh (accounting of the soul) every year. ‘Tis the season.

Weiss made a compelling case for using these days of t’shuvah (return) with a gentle touch. Yes, we want to think about the things we have done and said that could have been better, more thoughtful, kinder, more patient, more compassionate. And yet we could also, Weiss argues, turn those desired qualities inward and give ourselves the compassion we strive to give to others. What would it be like to refrain from parading our picayune sins before our own eyes once they have been proportionally atoned?

We all have seen someone make such a show of apologizing that it starts to look like they’re a little in love with how it feels to apologize, perhaps even a little in love with the sin itself. This, Weiss argues, is not t’shuvah. It’s vanity. I would even suggest it’s virtue signaling.

For me, t’shuvah ought not be cumulative. If I say or do something unkind on Sukkot, I should apologize and make t’shuvah by Simchat Torah, maybe even by Sh’mini Atzeret. Like the missed dose of medicine that should be taken as soon as you realize you missed it, so too with a necessary apology. It’s when you save up all the missed doses until the Yamim Nora’im (Days of Awe) and wallow in the guilt of it all that you risk, frankly, overdosing on regret and self-recrimination in such a way as to blow the individual doses out of proportion. Maybe it’s cathartic, sure, but it risks veering toward being depressing or even performative.

The Midrash teaches that the first Yom Kippur arose spontaneously as a communal response to the shame and guilt of having built and attempted to worship the golden calf. Maybe the snarky comment you made to your sister-in-law that hurt her actual feelings was properly redeemed when you apologized with sincerity. Recalling it at Yom Kippur and apologizing again carries the risk of reopening a wound for both your sister-in-law and for you.

So if we take a pay-as-you-go approach to t’shuvah, what are these days for? If we apologize as soon as we realize we should, and do so honestly, what’s left for atoning? Is my cheshbon hanefesh actually clean if I just make it a point to do t’shuvah proportionally and within the statute of limitations?

Nope. Not so fast.

I would argue that the Days of Awe — and the month of Elul that precedes them — are when we are called to level up and look at the constellations rather than the stars. Those moments of making prompt apology — are there themes that keep coming up? Do they involve a topic that is troubling me more deeply than I’m willing to admit? Do they tend to involve one person? One type of person? Do they come about when I am in a particular state or situation? (Hangry? Moi?)

In a meditation class I took a zillion years ago, the teacher admonished that the finger pointing at the moon is not the moon. I’m still puzzled over that, but here it seems clear that the small- to medium-sized sins that are attended to (relatively) easily in the moment might be pointing to the bigger questions, those where cheshbon hanefesh takes on its real meaning.

Returning to the metaphor of the medicine, maybe Yom Kippur is our appointment to recalibrate our dosage. If we know we tend to be snarky to our children when they come into the kitchen asking for a snack while we’re making dinner (I’m just saying) of course we should continue apologizing every time we do the same damn thing and snap at them, but maybe we could also have a gentle word with them about patience and self-sufficiency…and make sure the fruit bowl is well-stocked.

If we know that we squander opportunities for genuine connection with others because we are embarrassed by thus-and-such or because we think we could never bridge the gap we perceive between us, it is time to recalibrate. If we know that there’s someone who has been on our minds for months but we’ve never quite found the moment to get back in touch, it is time to recalibrate. If we know there’s chesed we could be doing but aren’t, it is time to recalibrate.

And if we know that we continually deny our own dreams, bypassing a half hour of study or Hebrew practice in favor of making one more semi-clever comment (or a thousand) on Facebook, it is time to recalibrate.