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The great Talmudic sage Reish Lakish offers two cryptic teachings regarding teshuvah – the mitzvah to spiritually “return” after we have sinned. He says that our z’donot (intentional sins) can be transformed into shegagot (unintentional sins). The Talmud (Yoma 86) immediately notes that Reish Lakish also said that our intentional sins can actually become zechuyot – spiritual merits.

The Talmud resolves this idea by stating that the difference is whether one repents from fear or love; repentance from fear downgrades intentional sins to accidental infractions, while repentance from love converts our sins into merits.


Yet this does not fully resolve the question: How can our sins be transformed into merits? The following three examples provide an answer: First, there is a Midrash that explains the relationship between the sin of the Golden Calf and the Mishkan . This Midrash teaches that the Mishkan was built in response to the Golden Calf. But what is the nature of that response?

The Golden Calf was built, as the name implies, out of gold – but what happened to that gold? The Midrash explains: “The Holy One, Blessed is He, said, ‘Let the gold of the Mishkan come and atone for the gold of the calf.’ Furthermore: The Holy One, Blessed is He, said to Israel, ‘When you made the Calf, you angered Me by saying “eileh elohecha is your god.” Now that you have made the Mishkan, with “eileh pekudei” (Exod. 38:21), I am appeased by you.’ In other words, the gold that was used for sinful purposes was not disposed of or discarded. Rather, the Jews were able to correct their sin – at least to a degree – by utilizing the gold itself for the mitzvah of building the Mishkan.

Second, there is the story of the biblical character Rachav. The Prophet tells us that when the spies Pinchas and Kalev came to her residence, she helped them avoid detection, and then further helped them escape by using a rope. The Jewish Sages point out that it wasn’t just any rope. It was the rope that men used to solicit her illicit services. Yet despite the fact that it had been used for hedonistic pursuits, she used the same rope for a constructive, positive goal – namely, helping Pinchas and Kalev escape so the Jews could conquer the land of Israel. Rashi, the great biblical commentator, tells us that she uttered a prayer: “Master of the universe, with these I have sinned. With these may You forgive me” (Rashi, Yehoshua 2:15, Zevachim 116b).

Third, there is a famous story of Reish Lakish, the very same Reish Lakish who teaches that teshuvah me’ahavah, repentance from love, transforms sins into merits. Reish Lakish had an interesting life. In his youth he was a bandit, a thief, and possibly even a murderer (see Talmud, Gittin 47a). Yet his encounter with Rabbi Yochanan prompted him not only to repent but to become one of the most important sages of his time. The Talmud Yerushalmi tells a story that a colleague of his, Rav Isi, was abducted one day, and it appears that the rabbis had abandoned all hope of rescuing him. It was only Reish Lakish, the thug-turned-scholar, who believed Rav Isi could be saved (Yerushalmi, Terumot 46b). As Rabbi Ari Kahn points out, “Rather than rejecting his past, Reish Lakish uses it – not to take life, but to preserve life” (The Crowns on the Letters, p. 300).

Here are three stories of people using their past sins for constructive, life-affirming and spiritually oriented ends. And these are not run-of-the-mills sins, either. These sins include the three cardinal sins of Judaism: The gold, once used for idol worship, is now used for the Mishkan. Rachav first used her rope for sexual immorality before using it to help conquer the land. And Reish Lakish used his aggression for pillaging and murder before using it to preserve his colleague’s life from the jaws of death.

We started with a question: How can repentance from love transform sins into merits? By transforming how we use our inclinations, skills, tendencies and our even possessions, we can transform a less-than-ideal past into a more G-d-conscious future. In my book The 40 Day Challenge: Daily Insights to Prepare for the High Holidays, I write, “If teshuvah is motivated by love, then we can take the negative energy of that unfulfilled promise and convert it into something positive. Our past shortcomings thus become reinvigorated and allow us to live a completely different life, because the Torah believes so deeply in the power of change and personal transformation. This is why Reish Lakish, a reformed gangster turned Talmudic sage, was able to say with all honesty and sincerity that if someone does repentance from a place of love, his sins are transformed into merits” (p. 140).

The month of Elul is a time to introspect, to celebrate the good we’ve done, and to recognize where we have stumbled. But the goal is not to ignore the mistakes and transgressions of our past but transform them into something positive: the gold from the Golden calf to build a Mishkan, Rachav’s rope to help Kalev and Pinchas conquer the land of Israel and Reish Lakish’s past life of thuggery to save a rabbinic colleague. Rather than denying our somewhat sullied past, we aim to redeem it by creating a better future.

My prayer for us this Elul and High Holiday season is that we think deeply about our strengths and our weaknesses. To the extent that we have fallen short, let us not deny those failures but use them as growth opportunities. In the coming year, may our weaknesses become our greatest strengths.

(The author expresses gratitude to Alec Goldstein for assistance with this article.)

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Rabbi Mark Wildes is the founder of Manhattan Jewish Experience, (MJE), a highly successful Jewish outreach and educational program that reconnects unaffiliated Jewish men and women in their 20s and 30s with Jewish life, and which is responsible for 377 marriages. He is the author of The 40 Day Challenge: Daily Jewish Insights to Prepare for the High Holidays (Kodesh Press) and Beyond the Instant (Skyhorse Publishing).