As we approach the end of Massekhet Yoma, the Gemara turns to the most essential issue of this holy day – the atonement offered by Yom Kippur itself and the teshuvah – repentance – associated with this time of year.
In a series of statements of amora’im praising the attributes of teshuvah, two statements made by Reish Lakish (who was, himself, a famous ba’al teshuvah) are presented. In one of them Reish Lakish argues (based on the passage in Hoshea 14:2) that teshuvah changes zedonot – sinful acts done on purpose – to shegagot – acts done by accident. In the second statement, (based on Yehezkel 33:19) he teaches that through the good offices of teshuvah, zedonot are turned into zekhuyot – merits.
To answer this apparent contradiction, the Gemara distinguishes between teshuvah that is done because of love – when zedonot turn into zekhuyot – and when it is done out of fear of punishment – when zedonot become shegagot.
How can evil deeds become good ones?
The Maharsha suggests what is, perhaps, the simplest explanation: that someone who repents out of his love for God is inspired by his past behaviors to be more meticulous than others in his accomplishments in the realm of Torah study and fulfillment of mitzvot. Thus it is as though his sins are the driving force behind his drive to perform mitzvot, so the sins can be seen as having positive merit. Furthermore, the Maharil Habib points out in his Tosafot Yom ha-Kippurim that a person who, by doing teshuvah, overcomes his desire to perform a sinful act is, by definition, accomplishing a more difficult task than someone who has never sinned and does not have the same desire. The ba’al teshuvah is rewarded for overcoming this desire, a reward that stems from the performance of the original sin.
Rav Yehuda describes a ba’al teshuvah as someone who is faced with the same scenario that led him to sin in the past, but overcomes his desire and refrains from committing the sin. The Rambam claims that finding oneself in the exact same situation – that is to say, being given the opportunity to do teshuvah – is one of the indications that your teshuvah has been accepted, something that not everyone merits.