Being Jewish
Commentary
The Best Approach to Teshuvah on the High Holidays

Last year, around Rosh Hashanah, I joked with my husband about why it was my favorite holiday. So much of the liturgy is about feeling lost and desperate for a mercy you aren’t sure you deserve. But for me, this is a relief.
“That’s a regular Wednesday in my head,” I said to his laughter. “It’s just nice that everyone’s on the same page for once!”
Indeed, I can still vividly remember the day I first paused to contemplate what has since become my favorite passage in the text. As a parent, I split my time during holidays between davening and chasing after my young children. I often find myself perched on a playground swing, reading the machzor more leisurely than when I’m in services, where I’m usually racing to catch up.
But on that day, four years ago, I lingered over the evocative list of similes for man at the end of the Unetaneh Tokef, a central prayer of the Days of Awe: He is “like a broken shard,” it says, or, alternatively, like grass dried up, a faded flower, a fleeting shadow, a passing cloud.
Like a broken shard. Nothing I had read before so perfectly captured the tenuous nature of being human, the way beauty and pain are all tangled up inside us. And yet I’ve sometimes worried that my attachment to such melancholic thinking could inhibit my resolve to do true teshuvah, or repentance.
Earlier eras were overly harsh in dealing with transgressions, but our zeitgeist has occasionally swung too far in the other direction, casting every misdeed in the gauzy, flattering light of being therapeutic. Buy too much junk on Amazon, neglect your obligations to your friends, engage in an unhealthy dalliance—today, it can all be excused as self-care.
This has often irritated me. If we lean on the idea of imperfection as inevitable or integral to identities, do we not risk seeing our flaws and foibles as somehow good?
But do I not fall prey to the same thinking? Every year, I enter the High Holiday season with earnestness, and every year, I fail to eradicate myriad sins from my repertoire. I want to be kinder to my children, but I overreact when they’re wild and then comfort myself with excuses. I sidestep difficult conversations, figuring that I am being nice and maybe being avoidant is a positive. I complain about my deficits and suffer as a result of them, yet they are also familiar and easy. How do I continue yearning for change while accepting that, like all people, I’m flawed and thus will likely fail?
Perhaps the problem isn’t the wrongdoings themselves, but rather in the waffling or wallowing in them. There are many inspiring Jewish texts instructing us on how to overcome sin. “The truly righteous do not complain about ignorance,” Abraham Isaac Kook, the first Ashkenazi chief rabbi of pre-state Israel, wrote, “rather they increase wisdom.” None of these exhortations by our sages allow for complacency despite our tradition’s acknowledgment of our brokenness.
We can recognize our human frailty as described in the Unetaneh Tokef and we can accept that we’ll likely have to return to the work of repair ad nauseam; what we cannot do is be complacent about our weaknesses or, worse, grow attached to them. Instead, we must be vigilant and believe we can overcome them, even while acknowledging that the work is hard and likely impossible. As the famous dictum from Pirkei Avot encourages, “It is not your duty to finish the work, but neither are you at liberty to neglect it.”
Lucky for us Jews, we have a lot of experience believing impossible things—a people decimated rises, a Jewish state is created—and witnessing them nonetheless come true.
Kelsey Osgood is the author of two books, including Godstruck: Seven Women’s Unexpected Journeys to Religious Conversion.
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