The Challenges and Unexpected Rewards of ‘Teshuvah’

Professor Louis Newman helps to launch us into the spirit of the month of Elul and the High Holy Days that follow.

This time of year our attention often turns to the subject of teshuvah, the dominant theme of the High Holiday season. The idea of teshuvah is closely related to its Hebrew root, which means “turn,” or “return,” but also “respond.” Usually translated as “repentance,” it is a complex concept that touches on many moral and spiritual issues—self-reflection, apology, reconciliation, personal growth and connection to God (however we may understand that), among others. For many Jews, teshuvah is associated with a heightened sense of guilt or even shame, and so we approach this season of the year with some trepidation, as if we are being asked to participate in a collective exercise of self-flagellation. But our tradition offers us a great deal of wisdom about the meaning and process of teshuvah that can serve us well, if we’re willing to take it in. Indeed, I suggest that we are all in need of teshuvah, and that the work we are called upon to do at this time of year (indeed, throughout the year) can enrich and even transform our lives in unexpected ways.

To appreciate the full significance of teshuvah, we need to begin by understanding that it operates simultaneously on multiple levels. It is about “turning inward,” engaging in genuine self-examination about who we are and what we have done. But it is also about “turning toward” those whom we have hurt, whether intentionally or inadvertently, in an effort to repair broken or damaged relationships. Finally, it is about “returning to the Source of our lives,” recognizing that however we understand the ultimate source of life and goodness in the world, we can only live meaningfully if we are connected with that Source. In short, teshuvah ideally connects us with ourselves, with others, and with a transcendent source of truth and goodness, or what Rabbi Mordecai Kaplan would have called, “the power that makes for salvation.” To engage in teshuvah is to become whole, to become the best selves we can be, and to live in harmony with others and with the universe. Given that teshuvah is such a multi-dimensional concept, it’s no wonder that it has been a source of such rich and varied reflections by Jewish thinkers across the centuries.

Many of those thinkers have emphasized the many steps in the process. While these have been defined in a multitude of ways by different rabbis, there is widespread agreement that teshuvah requires:

  • Acknowledgement of one’s misdeeds;
  • Apology to those we have harmed;
  • Genuine remorse;
  • Restitution for the harm we caused (to the extent that this is possible);
  • Introspection about the roots of our own misdeeds;
  • The determination not to repeat one’s transgressions;
  • A change of behavior, demonstrated by making the choice not to make the same mistake again when presented with the opportunity.

By any measure, this is a daunting list! It assumes that we are willing to hold ourselves accountable and to engage in the work of genuine heshbon ha-nefesh (“soul-reckoning”) that many, perhaps most, of us resist. Perhaps we already suffer from low self-esteem and so magnify our own failings disproportionately. Perhaps we have been hurt by the misdeeds of others in ways that make our own failings seem trivial in comparison. Besides, we did all this soul-searching last Yom Kippur and here we are again, feeling just as much in need of repair as ever.

In my experience, this is where many of us get stuck—in the sense that this work is incredibly difficult (if not impossible), and that it doesn’t really benefit us. We focus on the challenges, the obstacles that get in our way and the repetitive nature of the teshuvah process. And so we go through the motions half-heartedly or without much confidence that our efforts will change us for the better. What we are missing is a sense of hope—a belief that the work we are asked to do is genuinely going to make a difference.

The rabbis were surely aware of this problem, which is why they emphasized again and again that the process of teshuvah has remarkable, virtually miraculous, powers to transform our lives. Let’s look at just a few of their many teachings, which highlight the fact that teshuvah is not only an arduous task, but a blessing and a gift.

‘Open to Me, My sister’ (Song of Songs 5:2) According to Rabbi Yose, the Holy One said to Israel: My children, open to Me in penitence an opening as small as the eye of a needle, and I shall make an opening in Me for you so wide that wagons and coaches could enter through it. (Pesikta d’Rav Kahana 24:16)

Here the rabbis use a rather unremarkable verse from Song of Songs to make a remarkable point. God so wants us to engage in repentance that if we make only the most minimal effort, God’s gracious response will be many orders of magnitude greater. We need not do this work comprehensively or perfectly; we need only to make a start. Every move in the direction of teshuvah is meaningful. Restated in a less anthropomorphic framework, we might say that the universe is structured in a way that supports and magnifies our efforts to repent. We are not alone in this work. We should not despair that the work of teshuvah is too onerous or that it is pointless. Every effort we make will open up for us further opportunities for reconciliation.

The rabbis seemed to be virtually obsessed with extolling the efficacy of teshuvah. Indeed, they sometimes ascribe nearly magical powers to the work involved.

Resh Lakish said:  Great is penitence, because it reduces one’s deliberate sins to mere errors. But did not Resh Lakish say at another time: Great is penitence, because it transforms one’s deliberate sins into merits? There is no difficulty here: The latter statement refers to penitence out of love, the former to penitence out of fear. (Babylonian Talmud, Yoma 86b)

Leaving aside for a moment the distinction between penitence motivated by fear and by love, both of the statements ascribed to Resh Lakish are extraordinary. After all, how could it be that our deliberate transgressions could be retroactively “downgraded” by virtue of our teshuvah to the status of unintentional errors? Even more remarkable, how could teshuvah transform our past sins into merits?! Surely, the past is past; what we have done cannot be altered after the fact and given a different moral weight.

But it is precisely the rabbi’s point that genuine teshuvah accomplishes this sleight of hand. It is as if the penitent’s current state of remorse and resolve to do better in the future lessens the import of what he or she did in the past. Much as a modern-day criminal might get a reduced sentence by virtue of his subsequent good behavior or rehabilitation, the penitent demonstrates that she is now a significantly different person, the sort of person who will not engage in that transgression again. And that, says Resh Lakish, lessens the severity of the penitent’s past behavior. In this sense, teshuvah really can change the past, not by undoing what was done, but by compensating for it, which rebalances the proportions of good and evil in the world.

But it is in Resh Lakish’s second statement that an even more radical view of teshuvah emerges. One’s transgressions really can become one’s merits through the transformative power of teshuvah. For as Rav Kook explains in his remarkable book, Lights of Penitence, the misdeeds we have done, when we truly repent for them, become the engine that drives us toward greater righteousness. In his words,

One’s perspective is enlarged through penitence. … All that seemed deficient, all that seemed ugly in the past, turns out to be full of majesty and grandeur as a phase of the greatness achieved through the progress of penitence. … Thus will penitence serve as a force for good that literally transforms all the wrongdoings into virtues. (Lights of Penitence, transl. Ben Zion Bokser, Paulist Press, 1978, pp. 70-71)

The promise of teshuvah, then, is that we have at our disposal the power to lessen the mistakes we have made in the past; even more, we can grow beyond those mistakes, allowing them to propel us to greater levels of wholeness.  

This perspective on teshuvah is the antidote to the view so many of us have of this process. The point is not to bemoan our failings, much less to berate ourselves over them. It is to learn from them and to see them as a stage on our journey to becoming the people we are meant to be, that we have always wanted to be. In the inspiring words of Rabbi Adin Steinsaltz, “You should regard the faults as something constructive, like the beginning of a new and beautiful story.” (Strife of the Spirit, Jason Aronson, 1988, p. 101) How different might our experience of this season be if we adopted this perspective?  

At the root of this exceptionally positive way of approaching teshuvah is that it is predicated on the idea of our radical freedom. Of course, most of us think of ourselves as having free will, but rarely do we appreciate the full implications of that concept. Because being really free means that there is no limit to our ability to change ourselves. We are not stuck in the past; we are not destined to be in the same place again next Yom Kippur where we are now; we are not predisposed to falling into the same traps over and over. Indeed, we are not even required to bear the full guilt for our past transgressions, if we genuinely repent of them. Again, in Rav Kook’s words, “Penitence is the aspiration for the true original freedom, which is the divine freedom, wherein there is no enslavement of any kind.” (Lights of Penitence, transl. Ben Zion Bokser, Paulist Press, 1978, p. 54)

This is really what teshuvah offers us—a taste of radical freedom. Teshuvah is freedom from the mistakes of the past and from the compulsion to repeat them; freedom from shame; freedom from the shackles of self-deception, self-aggrandizement and self-denigration. Freedom to live a life of wholeness and integrity, freedom to become the people we were created to be. The idea that we are radically free in this way is arguably one of Judaism’s most profound contributions to the western religious thought. It can also help us approach these High Holidays with a sense of hope and possibility.

Our tradition offers us great wisdom about how we can overcome the mistakes of the past and turn toward a life of greater integrity and connection. To be sure, the path is not easy. It requires courage and persistence, unwavering honesty with ourselves and others, genuine commitment to reorient ourselves through a process of turning and returning, again and again. But the rewards of doing teshuvah can hardly be overstated. It provides us with nothing less than the opportunity to actualize our innate, Divine freedom. It invites us into a process of self-transformation and the promise of new beginnings. Teshuvah is a blessing and a gift, if only we choose to embrace it.

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