The Mesilas Yesharim (perek 4) says that according to the letter of the law there should be no room for teshuvah. He explains that this is because once the crime was committed how can one undo what was done? Can one bring back to life one who he has murdered? Says the Mesilas Yesharim, teshuvah only exists in the realm of lifnim meshuras hadin – above the letter of the law, with middas harachamim.
Rav Elchanan Wasserman, zt”l Hy”d, asked the Chafetz Chaim that this seems to be in contradiction with the Gemara in Keddushin 40b, that says if one is righteous his entire life, but rebels at the end of his life and regrets performing all of his mitzvos, he will lose the reward of performing all of his mitzvos. Says Rav Elchanan, we see that even without the middas harachamim when one regrets his previous actions, even his mitzvos, he will not be held accountable for them. Clearly, removing one’s reward is not the work of the middas harachamim. Why then does the Mesilas Yesharim say that teshuvah will work to remove one’s aveiros only in the realm of lifnim meshuras hadin?
The Chafetz Chaim answered that there are two forms of teshuvah; teshuvah m’ahava and teshuvah m’yirah. When one does teshuvah m’yirah he is not actually regretting performing the aveiros; he only fears the harsh punishment. As a result, he wishes to repent. This is an acceptable form of teshuvah, however this form requires the middas harachamim to remove the wrong that he has done. However, teshuvah m’ahava is when one wishes to repent because he honestly regrets that what he has done – he understands that it was wrong. In this case his teshuvah will remove the aveiros without the aid of the middas harachamim. When one rebels and regrets performing mitzvos, he has the same level of regret as one who has performed teshuvah m’ahava. Therefore, he will lose the reward for his mitzvos. Since when one honestly regrets his actions in the letter of the law they are removed, this can work to one’s detriment as well.
Rav Elchanan suggested another solution to his question. He cites the Mesilas Yisharim in his sefer Derech Hashem, who explains that when one performs any of the mitzvos besides the fulfilling of the commandment and listening to Hashem, he also accomplishes a tikkun and sheleimus. There is a purpose that is accomplished with every mitzvah that we are generally not aware of. The Avos were able to recognize these purposes and thereby understood what to do even before the Torah was given. Similarly, when one performs an aveira aside from not listening to what Hashem has commanded he has created something negative in the spiritual world.
When one regrets what he has done he only removes the aspect of whether he did or didn’t adhere to the command of Hashem. Whatever was created by his actions will remain even after one has regret for what he has done. Therefore, when one regrets performing mitzvos he will lose the reward of listening to the command of Hashem. However, the tikkunim and sheleimus that he created with his actions will remain and he will be rewarded accordingly for creating them.
All this is within the letter of the law. However, the Torah put into place with the mitzvah of teshuvah and by implementing the middas harachamim that when one does teshuvah and regrets performing the aveiros that he did, Hashem will remove even the negativities that he created when he performed those aveiros.
Therefore, there is no contradiction. Within the letter of the law, when one regrets his actions, we will not consider whether he had listened or had not listened to the command of Hashem. When one regrets his aveiros Hashem will also remove whatever negative effects were created with his actions.
May we all be zoche to reach teshuvah m’ahava and merit the revelation of Hashem’s kingship over the entire world. Amen.