Real Teshuva: The Hard Conversation
I have taught and attempted to live Teshuva, repentance, for some 50 years centered around two organizing principles. The first is that Teshuva is in itself a divinely ordained positive commandment of transformation that includes regret over misdeeds, leading to articulated confession of sins according to type and severity, abandonment of these violations, mending harm, especially interpersonal, and the promise to no longer act in a wrongful direction. I often taught this all in conjunction with a mystical view that locates sin as a break in God’s cosmos, and in the divine element of wholeness, that is the essential element in our spiritual DNA.
I can no longer use these two principles in comprehending, doing and teaching Teshuva. I certainly do retain a complete fealty and experience of the process derived above. But the organizing principles no longer speak to me clearly and compellingly. Understanding Teshuva as only one of 613 Commandments, to which we bend our will to the Almighty adds a defining element of coercion that rubs raw against the grain of true transformation. That outcome of real change must be experienced and accomplished as arriving from a profoundly free will and act. Lacking that element of choice renders the recital of the exhaustive list of confession, spiritually exhausting and exhausted of true meaning. It becomes a Jewish parallel to spinning a Tibetan prayer wheel in which we actually spin ourselves into a delusion that anything transformational has actually happened.
Associated with understanding Teshuva as externally forced behavior is the hoary image of a divine trial for us individually, and as a people in which we the accused are faced with an unflagging prosecutor, the katigor – besting one’s hapless defense, the sanigor. Alas, I sense that my own sanigor has evidently grown weary, and as we know, the caseload for public defenders is immense and crushing.
At the same time, mystical manipulation of divine spheres in the service of Teshuva has left me in this troublesome era, flat and disenchanted. In practice mystics strike me as engaging in a game of distraction with copious intentions (kavanot) and gesticulations that actually prevent a moral engagement with life. And today, the Rav Kookian theory of the inevitability of our peoples’ Teshuva – literally Return – meaning nationhood has been weaponized to serve immoral behavior, not by all, but by enough.
Desperately needing Teshuva that is at once existentially, meaningful and morally rational, I dropped the regnant theologies based on compulsion, mystical juggling or that of extreme nationalism. I returned to the Halakhic legal discussion. I focused on one phrase in Maimonides Laws (Mishneh Torah Teshuvah 1:1)
כשיעשה תשובה וישוב מחטאו חייב להתודות לפני האל ברוך הוא שנאמר: “איש או אשה כי יעשו וגו’ והתודו את חטאתם אשר עשו” (במדבר ה, ו-ז), זה וידוי דברים
“When one does Teshuva and turns away from sin, he is obligated to confess before God, Blessed is He… this is confession of words.
I approached this text with two questions: 1. How can a truly transformational act be compelled? 2. What actually is the actionable mitzvah of Teshuva?
The constantly daring commentary on the Sefer HaChinukh – a classic medieval compilation of the 613 Commandments – is the Minchat Chinukh (literally “A gift of Education” by Rabbi Yosef Babad 1801-74 Ternipol, Galicia). He offers in Mitzvah 364 an understanding which provides a radical response to my questions. He first seizes on the phrase in Maimonides “when one does Teshuvah” understanding it literally means that the act of Teshuva is itself a choice. Teshuva is not an obligation! It is not a positive commandment. Not doing it is not a violation – bitul mitzvat ‘aseh.
For the Minchat Chinuch, Teshuva is a choice, if you will, an opportunity. If so, then exactly what and when can the term “mitzvah” be applied. His answer is as startling as it is simple: If one chooses to do Teshuva, then one must do it properly and the core actual requirement is Vidui confession. One is obligated to confess, to do the Vidui in the proper manner.
This is, at first or second look, a strange construct: that the obligation -chiyuv- applies to the manner of performance, but not the large goal to which this process of confession is directed; that is, Teshuva. The Minchat Chinuch explains that this performance has a parallel in the mitzvah of divorce. Now there really is no Torah obligation for a man to divorce his wife. But the mitzvah is that if one decides to divorce his wife, he must do so in a fully legal and responsible manner, which includes the very elaborate bill of divorcement, the “get,” witnesses to its writing and delivery and court accessibility among other requirements to render her free. Deviation from the requirements produces only chaos and harm to her status and that of future children. So the actual obligation in divorce is performance focused. So too with Teshuva: a person‘s free will decision to do Teshuva needs to be centered on an effective Vidui. And if a real Vidui is lacking, then only a false transformation ensues. A real Vidui will engender regret, and attempts to repair the brokenness of moral violation.
The Minchat Chinuch description of Teshuva being a choice and Vidui being the correct, and therefore commanded, manner of Teshuva, has delighted many of the latter Halakhic analysts. Many cite other teachings of the Rambam that oppose it; and defenders have explanations and proofs for its adoption. But I don’t know of one who has fully accepted his theory. This interpretation needs a sanigor, and here is the defense: this approach affirms full human agency while being informed by Halakhic wisdom.
For Jews, human agency means taking full responsibility for your actions. If you hurt another unfairly, you must take ownership and seek to mend it. You, yourself must seek forgiveness from that person. And what applies to an individual is as if not more relevant to the nation. And then one -person and group – must mend the relationship with God that has been strained or seemingly broken by these wrongful actions.
And it is that final mending with God through self judgment, which can only be fulfilled by one’s choice. We experience that element in other dimensions of life: to get better physically, your fitness trainer will tell you “it’s all up to you” to fulfill the exercise regime honestly; no psychiatrist will take you as a patient, unless you have chosen to actually fully participate in self-examination; and while many fall in love, all of those fortunates soon face the choice of actual honest commitment to the relationship.
Choice is even more crucial with Vidui. In Halakhah, any statement or action performed under duress is meaningless as reflecting intention. Confession under duress is not you speaking, but only a repetition of what is scripted and expected by society. It would be what Sartre called “bad faith,” for it is not rooted in full acknowledgment of your own decision-making ability, which is at the center of your human identity. And that is the idea of the Minchat Chinuch in, deciding and choosing that you yourself will do Teshuvah through the Vidui process.
How to understand this confession? We are all aware or have been part of what is called “the hard conversation,“ that a parent has with a child, a teacher with a student, and very often a friend with a friend. In the hard conversation, pretense and jocularity and distraction are all dropped in order to speak honestly about intentions, speech, actions and consequences. It is hard for there is no defense when issues of great personal relevance and of great stakes are brought to the fore. In a hard conversation, there’s no going back. I refer to this as “the conversation,” for true care is the setting for what takes place. What takes place is no holds barred wrestling with one’s situation. Vidui is that confessing discussion that one has with oneself. It is placed in a social construct formally of the Yom Kippur liturgy, which allows for mutual support. The Vidui is in the plural to emphasize that we all have much at stake and no one is given a pass. And we refer even to the sins of our parents and ancestors, not as an excuse for our misdirection, but as a touchstone to our shared humanity that is painfully broken and needs release and transformation.
We recite the Vidui together – some parts in a dirge, but its fulfillment only comes when it reverberates in our hearts and calls us to change. It is not a magical incantation. If it does not hit us in all the tender and raw places, then it is “as if one immerses (in the mikvah for purification) while clutching a sheretz (repulsive unclean vermin) in one’s hand (Tosefta Ta’anit 1:8).”
We undertake this Vidui – our own personal hard conversation – in our community prayer places, but certainly less formally, but no less authentically on our own as we walk, muse, and meditate.
We do it as Rambam states “before God,” who is our standard for truth and moral being, and who is our ultimate judge. Then we can hope that we obtain a Teshuva, not merely an intellectual answer to our questions, but a return to what we perhaps once were and to where we can call home. This can only be reached without seeking existential shortcuts, moral excuses or perversions and a spirituality that is really only religious entertainment. We need to have that conversation with ourselves, no matter how hard. It is possible for it is done “before God,” who is “desirous of Teshuva.”

