When Teshuvah Feels Impossible

Nitzavim | Rosh Hashanah By :  Noam Blauer RS 2026 Posted On Sep 19, 2025 / 5785 | Torah Commentary
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This is taken from the JTS High Holiday Reader, To Be More Fully Human: Reflections on the Days of Awe 5786.

Are we really being set up for success for this whole teshuvah business? We might commit to doing all the preparation—journaling, going to shul, talking to therapists, chatting with rabbis, calling up hurt family and friends, New Year’s resolutions, etc.—and it still feels inadequate. Am I actually morally transformed? I am some infinitesimally small fraction of a hypermodern, global, complex network. My actions bear consequences for people on the other side of the globe I will never meet and whose names I will never even know. I still need to bring teshuvah to bear on my most intimate relationships,  but is this millennia-old process suitable to the messiness and uncertainty of modern moral life?

This seemingly modern plague of angst and cynicism is actually described in ancient Jewish texts, albeit in different terms. A halakhah in Tosefta Bava Kamma (10:14) reads:

הגוזל את הרבים חייב להחזיר לרבים. חמור גזל הרבים מגזל היחיד, שהגוזל את היחיד יכול לפייסו ולהחזיר לו גזילו, הגוזל את הרבים אין יכול לפייסן ולהחזיר להן גזילן.

One who steals from the masses is obligated to return [the object] to the masses. Stealing from the masses is more severe than stealing from just one individual, because one who steals from just one individual is able to appease that individual and return to him his stolen object. [In contrast,] one who steals from the masses is unable to appease them and to return to them their stolen objects.

This text addresses the severity of stealing from a broader community, which consists of many unknown people. Here are some contemporary examples: using an accessible parking space without a placard, holding onto a library book indefinitely, and riding the subway without paying the transit fare. These cases constitute theft from the masses in the broad sense—I don’t know my victims and have no idea how to make proper amends.

But once we identify the essential quality of this wrongdoing against unknown—and unknowable—victims, we can find more frequent occurrences than these. For instance, active or tacit engagement in political causes that, I’ve realized upon reflection, have actually had adverse impacts on others. Consumption of products that were produced in unethical and harmful ways. Actions taken that led to needless environmental devastation, felt by communities thousands of miles away. In trying to fathom the sheer number of unknown victims of my actions, whether in my own neighborhood or anywhere in the world, I might be convinced that I am truly awful and unworthy of teshuvah, thereby succumbing to an intense moral nihilism about my impact and the broader world.

Another passage from the Tosefta (Bava Metzia 8:26) has something powerful to say about this kind of response:

הגבאין והמוכסין תשובתן קשה, ומחזירין למכירין, והשאר עושין בהן צרכי רבים.     

“Charity and tax collectors—their teshuvah is hard. They return [stolen objects] to the people whom they know, and as for all the rest, they put it toward public needs.”

When this passage is cited in the Talmud (Bava Kamma 94b), Rashi makes clear that these are charity and tax collectors who defrauded the public and have no record of who they have wronged. The text affirms that their teshuvah is indeed hard. This simple wording from the Tosefta may be exactly the language we are looking for to describe our own situation: in modern society, our teshuvah is also hard. While not an endorsement of outright nihilism, there is a healthy acknowledgment of legitimate despair concerning living a righteous life in the face of moral complexity. Being in relationship with so many unknown people around the world is unfathomably hard; and despite our most serious efforts, teshuvah in that context is very hard, too.

Without dismissing or belittling this challenge, the Tosefta tempers this despair with a necessary measure of optimism. Even when teshuvah is hard, we must nonetheless return stolen items to the people whom we can identify as victims and give back broadly to public need. Rashi describes an example of the latter in which an individual helps build a cistern to provide fresh water to the community. While it may fall short of repaying the people I’ve specifically wronged, it enables me to engage in a kind of reparative mirror; I can positively and constructively engage in a moral act that will help people I don’t know and will never meet. This is a far cry from the heroic righting of wrongs I nobly imagined when I first embarked on this process. But it is something I can do and a deeply positive action worth holding onto.

In the spirit of these texts, bring this nuanced mindset entering into this holiday season: pursue teshuvah for all your wrongdoing, while being honest about the inexhaustible nature of this work. Be kind to yourself when acknowledging the many constraints and limits that lead to some moral failures and make up for them—however imperfectly—through heartfelt gestures of communal involvement and civic action. In short, turn teshuvah into a sacred opportunity to humbly affirm all the inherent joy and pain of what it means to live as human.

The publication and distribution of the JTS Commentary are made possible by a generous grant from Rita Dee (z”l) and Harold Hassenfeld (z”l).