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The Teshuva Process





This week’s article will discuss the mitzva of teshuva and its various components – cessation of improper behavior, regretting having done it, confession and resolutions for the future. How does this process enable us to change bad habits? And the fourth part, future promises, raises difficult questions — can we truthfully state that we will not repeat the same actions next year? In proclaiming our resolution, do we actually believe that we will not sin at all and not recite viduy at the end of 5781? And why, in the nusach of tefila do we find no mention of future resolutions? Some people seriously don’t think they will be able to hold out and feel like frauds at Slichos — their Rosh Hashana resolutions need a lot of rachamim to hold up till Neila. Can they say the words, knowing that next year will not just be a repeat? Of this and more in the following article.

The Mitzva of Teshuva

This week’s pararsha teaches of the mitzva of teshuva: “And you will return to the Lord, your G-d, with all your heart and with all your soul, and you will listen to His voice according to all that I am commanding you…” (Devarim 30:2). Eidot Hamizrach have been reciting Slichos for two weeks and Ashkenazim will soon join. This week’s article will take a closer look at the content of these prayers, and their practical application.

Teshuva – Easy or Hard?

We are all familiar with those heroic stories of ba’alei teshuva, people who left previous lives and embraced a life of Torah and mitzvos. For those born into life of Torah, teshuva seems like a daunting undertaking. And the Rambam’s words in Hilchos Teshuva seem to reinforce that understanding: “[He must reach the level where] He who knows the hidden will testify concerning him that he will never return to this sin again ” (chapter 2, halacha 2).

An additional challenge arises from the following words in Maseches Yoma: “One who says: I will sin and then I will repent, I will sin and I will repent, Heaven does not provide him the opportunity to repent, and he will remain a sinner all his days. With regard to one who says: I will sin and Yom Kippur will atone for my sins, Yom Kippur does not atone for his sins.” (85b). Many times, even while doing something wrong, one might recall Yom Kippur, calming himself that he will do teshuva until then. Does one who experienced that thought have any hope in light of the Gemara’s proclamation?

A third challenge arises from the Rambam’s description of what teshuva exactly is (Hilchos Teshuva chapter 2, halacha 2). According to the Rambam, the mitzva of teshuva consists of four stages: regret, cessation, confession and a future resolution. Regret and remorse may fill our hearts but how can we predict the future? How can one promise not to repeat past mistakes?

The Ramban in this week’s parashah explains the passuk “Rather,[this] thing is very close to you; it is in your mouth and in your heart, so that you can fulfill it” (Devarim 30:14) as referring to the mitzva of teshuva. The “thing” the Torah is referring to includes confession, regret and future resolution – in speech and mind, with full intention. The Torah states explicitly that this “thing” is “close to you”. It is nearby, easily attainable. Easy?

Rabbi Aber shlita in his sefer (Yesharim Darkei Hashem, Mamar Hateshuva) tells the story of a person who was requested to serve as a chazzan on the Yomim Noraim in his shul and was experiencing heightened anxiety. How could he, a person so filled with sin, represent his kehila before Hashem? He took his distress to Rabbi Aaron Leib Steinman zatal. After hearing him out, Rav Steinman looked at him quizzically, “What’s the problem? Do teshuva!” The man was dumbfounded. “When will I have time to do so much teshuva?”  Rav Steinman calmed him, “As you walk from your place to the amud, repent and confess your sins, and then you will be free of all sins and serve as an excellent shliach tzibbur.”

Rav Steinman was expressing a concept that appears in the Gemara in Kiddushin (49b): “If one says to a woman: Be betrothed to me on the condition that I am a righteous man, then even if he was a completely wicked man she is betrothed, as perhaps in the meantime he had thoughts of repentance in his mind and is now righteous.” The Shulchan Aruch paskens this l’halacha (Even Ho’ezer 38:31). All it takes is one small moment, one thought – and a total rasha becomes the greatest tzaddik. One second.

So how?

Different Kinds of Teshuva

The Rambam describes what full teshuva is: A person who is confronted with the same situation in which he sinned, when he has the potential to commit [the sin again], and, nevertheless, abstains and does not commit it because of his teshuva alone and not because of fear or a lack of strength has reached the level of full teshuva.

On the other hand, the Rambam continues and writes that even one who repented in old age after his life-force is spent, or when he technically has no ability to sin — and even one who repents on his deathbed is considered to have repented and is called a ba’al teshuva, his sins erased.

On the one hand for beginner’s teshuva — even one thought will suffice. But full teshuva is achieved when one is confronted with the same situation and refrained from it. Or, upon reaching the level that “He who knows the hidden” will testify that he will never return to this sin again.

Rabbenu Yona explains the differences (Sha’arei Teshuva 1:9): There are numerous levels of teshuva and at the level one merited to repent he will accordingly gain closeness to Hashem. Forgiveness can be attained even at the lowest level of teshuva, but the soul will not become completely purified without purifiying the heart and preparing the spirit. Rabbanu Yona compares it to washing stained clothes – after a basic laundering the garment is clean and major dirt is removed, but with every additional washing the garment comes out cleaner and cleaner, until finally it looks as clean as new. This is his explanation of the psukim that associate teshuva to laundering clothing: “Wash me thoroughly of my iniquity, and purify me of my sin” (Tehilim 51:4) and “Cleanse your heart of evil…” (Yirmiyahu 4:14).

This affords us a new perspective on the mitzva of teshuva: on the one hand, one can become a ba’al teshuva in one short moment and be, as the Rambam writes: “beloved and desirable, close, and dear” (Hilchos Teshuva chapter 7:6). But after the first repentance, we are obligated to redouble our efforts and deepen them, allowing our souls to rise to spiritual heights.

Changing Bad Habits

Rabbi Ya’akov of Lissa, the Ba’al HaNesivos (Drush l’Shabbos Hagadol 3) adds an additional dimension to this concept. The Lechem Mishne questions the Rambam’s words “He who knows the hidden will testify concerning him that he will never return to this sin again.” How can Hashem testify that one will not sin if there is free choice? As long as one is alive he has the choice to sin or to refrain from it – how can Hashem ever  testify in advance that one will not sin?

Rabbi Ya’akov explains that before sinning for the first time, one had free choice. Only then does he have the ability to truly choose to sin or not because at that point the pull of both is equal. Only before that first cigarette did the smoker have free choice about smoking and only then could he choose unbiasedly between smoking or not. The problem starts after the first sin – after that first drag. At that point an angel of destruction has been created. This angel is the angel of temptation. It constantly tempts a person with the same sin, and free choice is seriously compromised. In repentance, one severs his connection with the angel of temptation, essentially breaking the bad habit. With that, his angel of destruction is left to shrivel up and die, and one’s free choice is restored to its primal state. Knowing if all strings were indeed broken requires knowledge of “He who knows the Hidden”, but even before that, right at the beginning the penitent is already “beloved and desirable, close, and dear”. (For further clarification of free choice, see Rabbi Akiva Tatz, Will, Freedom & Destiny: Free Will in Judaism.)

A Small Resolution

Rabbi Yisroel Salanter teaches that breaking bad habits cannot happen at once, but in tiny increments. That small change, however minute, must be ironclad. One who speaks lashon hara regularly, for example, might begin keeping a ledger of nice things he finds in people with the goal of changing his negative outlook on the world. As one connects himself to a positive action, his is infused with a sense of positivity as well as a sense of accomplishment. This is the inner workings of mitzva goreres mitzva. If until now he had a negative angel, constantly tempting him with, for example, juicy tidbits of lashon hara, he has now severed his connection with that angel and established a connection with an angel of a mitzva that will protect and assist him. Eventually, one discovers that his habits have changed – he no longer feels tempted to repeat lashon hara. From now on, refraining from lashon hara is easy. The Sfas Emes (Devarim, Shabbos Teshuva, 5638) explains that “He Who Knows the Hidden” is the only one privy to this knowledge because the process is gradual and slow, so slow that even the person himself is not always aware of the changes taking place. He even does not know that eventually he will never sin again. Only “He Who Knows the Hidden” can testify of it.

A small resolution that changes one’s direction has the power to make a complete overhaul in the end, but choose your resolutions with care. They must be resolutions that will generate change; obviously a resolution to recite Birkas Hachama with kavana won’t do the trick.

The Gemara (Maseches Shabbos 88a) describes the teshuva the Jewish nation did in the days of Mordechai and Esther. Their teshuva was of the highest level – teshuva me’ahava – repentance out of love. Nevertheless, upon reading Sefer Ezra we find the nation, those same people who repented on such a high level just several years before, committing some of the gravest sins – mixed marriages, chilul Shabbos and more. How does this coincide?

The answer provides a clear illustration of the nature of teshuva. Teshuva is a process. Those first steps that the nation took during the days of Mordechai and Esther were what enabled Ezra and Nechemia to demand their separation from their non-Jewish wives and total Shabbos observance.

Teshuva at Your Own Pace

The Rambam (Hilchos Teshuva 1:1) writes that whoever confesses profusely and elaborates on these matters is worthy of praise.  On the other hand, the Ramchal, in his introduction to Mesilas Yesharim, denounces prolonged confessions and fasts: “Most people imagine piety consists of reciting many psalms, very long confessions, difficult fasts, and immersions in ice [water] and snow – all are things incompatible with intellect and which reason cannot find peace.”

A close reading of the Ramchal provides the solution. Teshuva, return to Hashem, is not a difficult thing. It can be done while walking from one’s place to the amud.  It is the imagined piety that is difficult. Confessions are praiseworthy if that’s where you’re holding, but if they feel “very long” and the fasts seem “difficult” –they are incompatible with intellect. Only when coming from a place that completely makes sense to you, on the personal level, are they praiseworthy and appropriate. When piety seems to depend on perceived strenuous activity they are unnecessary and inappropriate. They are not the Jewish way.

Repentance must occur at your own pace, one step at a time. Growing closer to Hashem is a process that takes time, a lifetime. But taking these steps is the human responsibility.

The Cycle of Sin

The Tania explains the above-stated Mishna (Yoma 85b): “One who says: I will sin and then I will repent, I will sin and I will repent, Heaven does not provide him the opportunity to repent” as only applying when at the time of sinning the person still has the possibility to stop himself, but he nevertheless allows himself to sin because of Yom Kippur’s opportunity for repentance. But one who struggled with himself and succumbed, even if he comforts himself while indulging in sin with the knowledge that Yom Kippur is coming and repentance exists, is not included in this category.

In addition, the Rambam (Hilchos Teshuva chapter 4:6), after detailing the obstacles to teshuva including the above-mentioned approach, writes that those things do not in any way prevent one from teshuva. They only serve as an obstacle and make teshuva more difficult. If despite the difficulty one does repent in the end, he is a complete ba’al teshuva and merits his portion in the World to Come.

The Rambam in Hilchos Teshuva (chapter 6:4) lists the ways for doing teshuva when there are obstacles blocking one’s way. Indeed, most people experience them, to varying degrees. Tzadikim and Neviim prayed to succeed in doing teshuva, begging Hashem that their sins not hold them back.

Future Resolutions

The Rambam (Hilchos Teshuva chapter 1:1) provides the text for viduy:

How does one confess: He states: “I implore You, G-d, I sinned, I transgressed, I committed iniquity before You by doing the following. Behold, I regret and am embarrassed for my deeds. I promise never to repeat this act again.”

This formula appears in other Rishonim as well: Smag (positive mitzva 16); Sefer Chassidim (chapter 20); Orchos Tzaddikim (Sha’ar Hateshuva); Maharam of Rothenburg (siman alef, 23).

The Aderet (Bnei Binyamin chapter 1:1) questions why almost all poskim fail to mention the required future resolution, so such so, that it is not mentioned in the viduy of any siddur or machzor!

Indeed, the various mefarshim wonder from where the Rambam learned this obligation. They indicate to two possible sources:

Rabbi Yosef Albo (Sefer Haikarim, ma’amar 4:26) and Ma’ase Rokeach (Teshuva 1:1) indicate that the source is the passuk in Hoshea (14:3-4), those final psukim read on Shabbos Shuva: “Take words with yourselves and return to the Lord. Say, “You shall forgive all iniquity and teach us [the] good [way], and let us render [for] bulls [the offering of] our lips. Assyria shall not save us; we will not ride on horses, nor will we say any longer, our gods, to the work of our hands…”. Not returning to the previous sin is part of the teshuva process as described in these psukim.

Many other commentaries on the Rambam (Daas Kedoshim, Tziyunei Maharan, Keser Hamelech, Avodas Hamelech) explain that this approach is also found in the Yerushalmi (Yoma, chapter 8:7): “How does he confess… I sinned, and did evil, and I was situated in an evil state of mind, and in a faraway place I was walking, and as I did [in the past], I will not do. May it be Your Will… to forgive all my sins…”

This Yerushalmi explicitly mentions the need for a future resolution as part of the teshuva process. Why was this dropped from the machzor?

The Future Vow – Integral or Not?

From most Rishonim it seems that the commitment not to repeat the sin is dropped intentionally. Even the Rambam in Sefer Hamitzvos (positive mitzva 73) spells out the viduy text without mentioning a promise to never repeat the aveira. A similar text is also found in Sefer Hachinuch (mitzva 364). Therefore, it seems that the Rambam didn’t see the future resolution as binding l’halacha, without which teshuva is not accepted. The future vow, though an appropriate part of the main confession, in no way prevents teshuva from being accepted.

L’ahalacha, in the Shulchan Aruch (607) this obligation does not appear at all. The Magen Avraham (156:2) and Mishna Brura (ibid, 4) when detailing the obligation to confess every sin, do not mention an obligation to explicitly state one’s intention not to repeat that sin. Therefore, it seems that even one who repented and fully regretted his sins, but cannot promise never to repeat it has fulfilled the mitzva of teshuva. This seems especially true since this halacha is not mentioned in the Talmud Bavli.

Different Teshuva Approaches

To further clarify this point, the Yerushalmi (there) quotes Rabbi Yehuda ben Bteira’s approach to viduy: one must specify exactly which sins he committed – I ate milk with meat; I didn’t give tzedakah; I transgressed hilchos borer on Shabbos. This is contrary to Rabbi Akiva’s approach that only obligates one to state a genera proclamation: “I sinned, I transgressed, I committed iniquity before You “. Superficially, this seems like a disagreement on the wording of the viduy formula, but in truth, this dispute illustrates a difference in approach to the entire concept of Teshuva.

Rabbi Yehuda ben Bteria’s approach sees teshuva as the obligation to correct every sin individually – learn hilchos Shabbos so you never are mechalel Shabbos again; learn hilchos Shmiras Halashon so you never again tell lashon hara. Rabbi Akiva sees teshuva as a path in life, a direction. Teshuva according to Rabbi Akiva is a change in direction, a recalibration of our focus in life. Rabbi Akiva sees viduy as a general proclamation of having strayed from the direction of spiritual pursuit and requires expression of those things that caused us to stray from Hashem.

The obligation or lack thereof, of a future resolution, follows accordingly. According to Rabbi Yehuda ben Bteira teshuva is an individual process for every particular sin, therefore correction is made when one takes a vow to never repeat the deed. But Rabbi Akiva maintains that teshuva must focus on the general direction in life, as Yeshayahu describes (55:7): “The wicked shall give up his way, and the man of iniquity his thoughts, and he shall return to the Lord, Who shall have mercy upon him, and to our G-d, for He will freely pardon.” Repentance is not for a particular inequity, a specific aveira, but for the way — the general mindset that caused sin. When one focuses on recalibrating his mindset — abandoning the thought patterns that caused sin, and finding a small act that he can do to solidify his change of direction – that is a vow for the future.

Therefore, the Rambam, following his approach, writes (Hilchos Teshuva chapter 1:1) one must spell out in detail every sin, as per the ruling of Rabbi Yehuda ben Bteira. He continues and rules that one must vow to never repeat that sin again. But the Shulchan Aruch paskens (Orech Chayim 607:2) that the sins do not need to be spelled out. Apparently, this was accepted as the mainstream halachic ruling by those who arranged our siddurim and machzorim. Therefore, they did not mention the obligation to vow never to repeat past misdeeds.

Prayer or Resolution

Rav Eliyashiv is quoted as saying that the text of the viduy, “May it be Your will that I will not sin again” recited at the end of the viduy on Yom Kippur qualifies as a resolution for the future. How can a prayer serve as a vow or resolution?

Rabbi Luxenberg shlita explains (Drashas Shabbos Shuva, Neot Simcha 5778) that one can only do what is in his power to do. The Yetzer Hara, we are told in Kidushin 30b “overpowers him every day, and seeks to kill him, as it is stated: “The wicked watches the righteous and seeks to slay him” (Tehilim 37:32). And if not for the fact that the Holy One, Blessed be He, assists each person in battling his evil inclination, he could not overcome it, as it is stated: “The Lord will not leave him in his hand” (Tehilim 37:33). So really, the only way to overcome the Yetzer Hara is to pray for Heavenly assistance. And praying for it is the only action that can help to stave it off, which is the essence an expression of that future vow. This is also the Rambam’s approach (Hilchos Teshuva chapter 6:4) – the way to achieve teshuva when there are obstacles on the way is to pray to Hashem.

I Can’t Promise

What should one do if he really wants to correct his ways and change, but knows himself — he truthfully cannot promise, or even hope not to repeat past sins. He knows himself – those resolutions hold up perhaps until Neila, not more. What can he do? Does he have any hope?

Yes, says Rav Moshe Sternbuch in Teshuvos Vehanhagos (volume 5 chapter 41), quoting the Meiri in Chibur Hatshuva. The seir hamishtaleiach, the scapegoat sent to the desert brings kapara even without teshuva. The Meiri writes that it is impossible to say that it cleanses of sin even without regret, because then it falls into the category of a sacrifice of the wicked which is an abomination. What does this goat atone for? The Meiri explains that it serves as atonement for one who regrets his misdeeds but knows that it won’t last. This person is not a rasha, but his teshuva is incomplete. For a private person’s sacrifice, one needs to do full teshuva and correct his sins, each one individually, resolving to never repeat them. But for a public sacrifice, as we see from the scapegoat, regret alone will suffice. Therefore, Rav Sternbuch deduces that one who knows he will probably repeat his sins again next year despite his heartfelt regret, should make sure to pray with a tzibbur, effectively earning his teshuva’s acceptance albeit on its lower level, without the resolution for the future.


Teshuva is not an impossible mountain or daunting task but, as we see from the Ramban, very close and accessable, “in your mouth and heart”. Teshuva begins with the decision to change gears, experiencing sincere remorse for past sins. This makes one beloved by Hashem. Full teshuva, though, is a higher level – attained when one succeeds in changing his habits and achieving the free choice he had before he ever sinned – having no habitual temptation to sin. This can be achieved through small, minor but steadfast and consistently accumulative resolutions together with the deep heartfelt remorse for the past misdeeds and viduy. And as for the future – pray from the depth of your heart to Hashem never to sin again.

Shana Tova!

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