With Yom Kippur just passed and Hoshanah Rabbah on the horizon, the Jewish consciousness is still contemplating matters of teshuvah.  The focus naturally encompasses questions of individual conduct, relationship with God, and relationships with others.
In its practical manifestation, engaging in the process of teshuvah is often seen as an individual pursuit. Correcting one’s ways, addressing previous misconduct, aspiring to improve one’s future conduct, and making amends to others are seen as tasks to be managed by the penitent individual alone. This attitude is reflected in the proliferation of self-help and DIY-style guides to teshuvah now so abundant in bookstores and online.
Whilst not erroneous, the approach just described is often insufficient. Circumstances can (and often do) present obstacles to a person’s teshuvah which they cannot hurdle alone. One banal illustration: Reuven has wronged Shimon and wants to set things right. This is easier said than done as navigating a relationship of enmity demands immense subtlety and sensitivity.
In fact, the need for particular sensitivity when dealing with relationships between estranged parties is not limited to teshuvah; more general examples of conduct pertaining to strained interpersonal relationships can also be found in Halakhah. For instance, Rema (Shulhan Arukh Yoreh De’ah 335:2) writes that one should not visit an enemy when they are ill or to offer consolation for the loss of a relative, lest it be assumed that the visit is only for the purpose of gloating. Shakh comments and rejects such a blanket rule arguing that it all depends on the circumstances and sensitivities of the unique relationship at hand. Of course, it is also possible that a visit done correctly could mend the relationship.
It goes without saying that not all people are blessed with sufficient sensitivity to traverse such murky waters; even with a formula in hand, dealing appropriately with such cases will often only be possible with consultation and guidance from another person.
The need for assistance in navigating relationships is not the only time one might require external assistance in teshuvah. This will also be necessary in cases where an individual finds themselves unable to stop committing misdeeds alone. In this regard we can note the statement of Rabbi Akiva: “in the beginning it [sin] looks like a thread of a spider, and at the end it becomes like the rope of a ship” (Genesis Rabbah 22:6). Rabbi Akiva observes the psychological phenomenon of habituation in which an individual can become unable to resist performing activities—in this case prohibited activities—which they have engaged in regularly over a period of time. They find themselves tied, as it were, to those activities as if by thick ropes. In such a case, outside help will need to be sought if they are to rectify their ways and engage in teshuvah.
What is true for those struggling with a particular sin or sins is also true for more extreme cases. This is discussed by Rambam in the Mishneh Torah (Hilkhot De’ot 2:2):
Even so are people whose souls are sick; they desire and love the evil tendencies, and hate the good way, and are lazy to follow it, for it becomes a very heavy load upon them, in proportion to their ailment… And what is the corrective measure for the soul-sick? Let them go to the wise who are doctors of the souls and they will heal their disease with tendencies wherein they will instruct them until they will bring them back to the right way. And they that are conscious of their evil tendencies and do not go to the wise to be cured by them, concerning them Solomon said: “Wisdom and instruction fools alone despise” (Proverbs 1:7).
Rambam here is not addressing cases where a person struggles with a particular behavior or sin, but a far broader issue where the person’s whole approach to life has gone awry on the psycho-spiritual level. In such a case, he writes, one must seek out expert help.
Indeed, on Yom Kippur itself, the pinnacle of teshuvah, the service begins with Kol Nidrei and the annulment of vows. One might find a nod to external assistance in teshuvah in this phenomenon. In the halakhic sense, the annulment of vows speaks to the fact that sometimes the binds that one places upon oneself cannot be lifted alone, rather they need to be untied by another; as Rambam summarizes, “No one can absolve himself from his own oath…he should apply to a sage, or to three laymen if no sage is available” (Mishneh Torah Hilkhot Shavuot 6:1-3).
There are many cases of the teshuvah process in which benefit would be gained from the counsel of others. Guidance could aid with prioritizing different elements of teshuvah or provide context and deeper understanding of the teshuvah process. It might also be useful to provide a framework of accountability.
This brief sketch is intended only as an illustration of some of the reasons that one might be required to seek help in teshuvah. From the converse perspective, this might suggest that we should lend a helping hand, when solicited, in the teshuvah process of others. The question then becomes, how is providing help to others halakhically conceived? In other words, is there a specific obligation in Halakhah to help others with their teshuvah? The rest of this essay will attempt to show that there is such an obligation.
One could immediately turn to more general halakhic principles and suggest that they might generate an obligation to assist others with teshuvah. The following statement of the Rambam comes quite naturally to mind: “‘You shall love your neighbor as yourself (Leviticus 19:18)’; that is, whatever you would have others do to you, do to your brothers in Torah and precepts” (Mishneh Torah Hilkhot Evel 14:1). However, the task of this essay is to suggest something far more narrow, targeted, and specific. To this end we now turn to a close analysis of a Midrash Halakhah in the Sifre.
As background, Deuteronomy 22 presents the obligation to return a lost item to its owner:
(1) You shall not see your fellow’s ox or sheep go astray and hide yourself from them, you shall return them to your fellow. (2) And if your fellow is not near to you, or if you do not know him, then you shall bring it to your house and it shall be with you until your fellow seeks it out, and you shall return it to him.
The final phrase “and you shall return it to him” is superfluous as it expresses that which is already implied by the verse. With this in mind, the phrase becomes the subject of a Midrash Halakhah (Sifre Devarim Piska 223): “‘And you shall return it (ve-hashevoto) to him’— you even return himself to him.” The suffix of “ve-hashevoto” (literally, “return him/it to him”) can mean either ‘it’ or ‘him’ depending on context, therefore while the plain meaning of the phrase is rendered “and you shall return it to him” referring to a particular lost item, the Sages deliberately reread the phrase as “and you shall return him to him.” In other words, there is a Midrash Halakhah which says that one has an obligation to return a person to themselves.
We must then ask ourselves what the Midrash means: how would an obligation to return a person to themselves manifest practically? To answer this, we turn to the Talmud in which we find this Midrash featuring twice, and each time its practical import is presented differently.
In Bava Kamma 81b the Midrash is understood to be obligating us to help a lost person find their way back:
From where is it derived that the requirement applies even to returning his body [i.e., helping a lost person find his way]? The verse states: “And you shall return it to him.”
In Sanhedrin 73a it is understood to be obligating us to save someone’s life when they are under attack (such as from wild animals or bandits):
From where is it derived that one who sees another drowning in a river, or being dragged away by a wild animal, or being attacked by bandits, is obligated to save him? The verse states: “You shall not stand idly by the blood of another” (Leviticus 19:16). But is this really derived from here [i.e., this verse]? It is derived from there [i.e., from a different verse, as it says]: From where is it derived that one must help his neighbor who may suffer the loss of his body? The verse states: “And you shall return it to him” (Deuteronomy 22:2).
Despite the different applications and the slightly different language used in each case, the phraseology and identical exegeses means that we are undoubtedly dealing with the same Midrash. That the Talmud brings the same Midrash Halakhah with such apparently dissimilar applications could indicate that over time the original application was either lost or forgotten, leaving us with different traditions.
Yet there is another application of this Midrash which might furnish us with an alternative approach to addressing our question. Rambam (Peirush Ha-Mishnah Nedarim 4:4) writes:
A doctor is obligated by [Torah] Law to heal the sick members of Israel. It (the obligation) is included in their (the Sages’) [legal] explication of the verse “you shall return it to him” (Deuteronomy 22:2) [which is interpreted] to include [an obligation to return] ‘their body’ [to them], such that if one saw them deteriorating and was able to save them, then one must save them…with [medical] knowledge.
In this paragraph “return him to him” is understood to be referring to returning someone’s health to them. Although a reasonable extension of the life-saving case previously seen in Sanhedrin, this is still a halakhic innovation of the Rambam. Rambam justifies his novel approach by suggesting that the Midrash encompasses a range of cases rather than referring to a singular point of law, thus allowing his case (the provision of medical assistance) to be included within the more general precept.
Perhaps this can be taken a step further. If we understand the Midrash Halakhah as mandating a general obligation to prevent loss to the physical body of another, whether it be a risk to life or a risk to health, then the obligation to aid someone who has lost their way (the case in Bava Kamma) would appear to be an outlier. However, upon further reflection, we must note that when someone has lost their way, their situation often entails elements of physical danger such as a lack of access to sustenance, suitable shelter, and the like. Understood in this light, the case in Bava Kamma might well be primarily referring to saving someone from the perils entailed in being lost rather than merely pointing them in the right direction. If this is correct, then all the cases we have seen would align under the general principle of striving to prevent loss to the physical body of another or, in the words of our Midrash, the obligation to “to return him to him.”
Following this analysis of Rambam, we are dealing with a Midrash carrying broad halakhic implications. Thus far we have focused on very physical threats to the human body, but in our context we can suggest that it might well encompass the obligation to help another in their teshuvah process as well.
Teshuvah, which literally connotes a return, can be construed as ultimately being a return to one’s true self, unencumbered by sin or twists of character, free from interpersonal disputes, and free from those things which block us from a relationship with our Maker. As we have seen, individuals are often incapable of returning to that point (to themselves) without external help. As such, assisting another in their teshuvah process, in helping them to return to themselves, might well be an obligation encompassed in the injunction of the Midrash Halakhah.
The idea that the teshuvah process will often require outside assistance has largely been overlooked in the literature. Acknowledging this reality demands from us vulnerability, courage, and honest self-appraisal which (although not easy) are crucial for teshuvah. The notion that there may exist a formal obligation to help others in their teshuvah process is significant and demands from us sensitivity, wisdom, and care. Promoting both elements will surely lead to beneficial developments for teshuvah, both on the individual level and for all Klal Yisrael.
 I am indebted to Eli Shaubi, R. Joseph Dweck, R. Michael Harris, and Naomi Cohen for their insights and contributions to this essay.
 For more on Midrash Halakhah see Rambam Mishneh Torah Hilkhot Mamrim 1:2; see also Amon Bazak, Fundamental Questions in the Study of Oral Law (Yedioth Aharonoth Books, 2020), 92-211 (Hebrew). For a bold take see Jose Faur, “Law and Hermeneutics in Rabbinic Jurisprudence: A Maimonidean Perspective,” Cardozo Law Review 14 (1993): 1657-1679.
 See Louis Finkelstein, Sifre on Deuteronomy (New York: JTS, 1969), 256-7 which documents all the various versions of this Midrash on record.
 In Sanhedrin it says “Aveidat gufo minayin? Talmud lomar ve-hashevoto lo” and in Bava Kamma it says “Hashavat minayin? Talmud lomar ve-hashevoto lo.”
 This is also the conclusion of Finkelstein (above, n. 3). By omission, this is also in all likelihood the view of Tosafot (Sanhedrin 73a s.v. “talmud lomar”).
 It seems to have been motivated in part by the need to explain the Mishnah in Nedarim. See further in Rambam’s explanation of the Mishnah in Nedarim 4:4, and also Mishneh Torah Nedarim 6:8.
 Nearly all versions of the Midrash, including both in the Talmud and that of the Rambam, make reference to the body itself— “gufo.”
 Rav Kook, Orot Ha-Teshuvah 15:10. See also Mishneh Torah Shemitah and Yovel 13:13 where he uses the phrase “As God made him.”