Note: this article is an extract from Rabbi Chaim Drukman’s book, “La-zeman Hazeh,” a series of essays about Jewish holidays, including new ones that were established in the last hundred years to celebrate the Jewish people’s return to the Land of Yisrael.
Adapted and translated by Moshe Goldberg
The Power of Teshuvah (Repentance)
In Tractate Yoma (86b), Reish Lakish descrobes the tremendous power of teshuvah:
Reish Lakish said: Great is teshuvah, for intentional sins can become unintentional errors, as it is said: “Return, O Israel, to the Lord your God, for you have stumbled in your iniquity” (Hosea 14:2). But “iniquity” refers to deliberate sin—yet the verse describes it as mere “stumbling!”
The description “you have stumbled” fits something accidental — a mistake, an unintentional misstep. Yet the word “iniquity” refers to a deliberate, willful sin. From this, Reish Lakish concludes that through “Return, O Israel” — that is, through repentance — an intentional sin is transformed into an accidental one.
But the Gemara is perplexed, since Reish Lakish himself said something even stronger regarding the effect of repentance:
Reish Lakish said: Great is repentance, for intentional sins become merits, as it is said: “And when the wicked one turns from his evil and does justice and righteousness—through them shall he live” (Ezekiel 33:19).
Repentance does not merely turn intentional sins into mistakes, but into merits! Not an “accidental stumble,” but actual merit, even a mitzvah.
How can these two statements by Reish Lakish be reconciled?
The Gemara answers: There is no contradiction. Sins become merits when one repents out of love. Sins become mistakes when one repents out of fear.
If a person returns to God out of love, his intentional sins are transformed into merits. If he repents only out of fear, his sins are merely downgraded to accidental mistakes.
At first glance, Reish Lakish’s teaching is hard to understand. How can it be that willful, deliberate sins become merits?
Indeed, after the prophet says: “When the wicked turns from his wickedness and does justice and righteousness—through them he shall live,” he records Israel’s reaction: “And you say: The way of the Lord is not fair!” (Ezekiel 33:20). And clearly — how can this promise be true?
Sins Leading to Merits
We begin with an explanation by the Maharsha (Yoma 86b): “When one repents out of love … his repentance will be complete teshuvah and adds extra good deeds, beyond what is required in relation to that sin. Those added good deeds are counted for him as merits.”
According to the Maharsha, it is not that the sin itself turns into a merit. Rather, because of the sin, the person is moved to do more good deeds, so that ultimately he attains even more merits than before.
Rav Kook (Orot HaTeshuvah, end of chapter 1) follows a similar path but highlights a different point. “Teshuvah from love is filled with endless joy. It transforms all sins into merits — from every mistake it draws forth lofty lessons, and from every failure it creates exalted ascents. This is the teshuvah for which all eyes yearn. It must come, and it will come.”
Just as someone who misunderstood a subject but then discovers his error often ends up with a deeper and stronger understanding than if he had grasped it correctly the first time — so too with sin. When one commits a sin and then reflects on it through repentance, he is led to profound insights and powerful resolve. Thus, the very sins — through teshuvah from love — bring him to new merits, lessons, and growth.
And Rav Kook adds a deeper insight (ibid. 7:1): “The vision of repentance transforms all sins, with their terrors, spiritual pains, and ugliness, into concepts of delight and joy — for through them a deeper understanding shines forth, a mighty love of good and an intensified hatred of evil.”
Thus, repentance influences a person both to hate evil and to love good. In this way, the sin itself becomes the cause of growth—making the sin itself the very source of merit.
Our Sages illustrate this with a verse in Micah (7:8): “Do not rejoice over me, my enemy! For though I have fallen — I rise; though I sit in darkness—the Lord is my light.”
The Midrash (Yalkut Shimoni, Micah 552) comments: “Though I have fallen I rise.” Had I not fallen, I could not have risen. “Though I sit in darkness the Lord is my light.” Had I not sat in darkness, I would not have had light.
At first glance, this seems puzzling. Would it not be better never to have sinned? However, the lesson is that after a fall a person can rise higher than he was before. Without falling, he would never have reached such an elevated level. Thus, through the fall, he reaches greater heights than before.
We have seen that the true meaning of “sins turned into merits” is that because of repentance from love a sin pushes a person to greater devotion and more good deeds (Maharsha). One learns from failures, gains deep life-lessons, and becomes more vigilant in the future (Rav Kook, part 1). Repentance engrains in the soul a stronger hatred of evil and love of good than before (Rav Kook, part 2).
However, that these explanations do not literally fit with the wording “sins become merits” — in these approaches, the sin itself is not transformed but rather indirectly leads to additional merits.
Redirecting the Energy of Sin
If we go to a deeper level, there is indeed a way in which the sin itself is transformed into a merit. Rav Kook writes (Orot HaTeshuvah 9:8): “Repentance operates on the very will that led to sin — a desire of great force, strong enough to even break moral conviction. Then, once the sin is uprooted and redirected, it does not disappear. Rather, with its full power, it is redirected into the foundation of the world, imprinting in existence itself a mighty will for light and goodness. And in this way, intentional sins are turned into actual merits.”
A will strong enough to commit a deliberate sin has tremendous energy—it can break barriers, defy convention, and push past all norms. When redirected by repentance, that very force becomes a power for greatness and blessing.
Similarly, Rav Kook adds (ibid. 12:1): “Teshuvah lifts a person above all the low levels of the world, yet it does not estrange him from the world. Rather, he elevates the world and life itself along with him. The same drives that once led to sin are purified within him. Through teshuvah, the powerful will that led to sin becomes a positive force, bringing about wondrous and lofty deeds and many blessings.”
Thus, through repentance, the same energy of desire that once produced sin becomes a source of merit and blessings. And this is the true meaning of the declaration that “sins are turned into merits.”