#344: Feeling Bad Is Part of Being Good

Sha'arei Teshuvah on Regret

Photo by Kenny Eliason on Unsplash

Gimme Some Torah #344

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Sha’arei Teshuvah 1:10

עתה נבאר עיקרי התשובה: העיקר הראשון - החרטה. יבין לבבו כי רע ומר עזבו את ה'. וישיב אל לבו כי יש עונש ונקם ושלם על העון. . . ויתחרט על מעשיו הרעים. ויאמר בלבו מה עשיתי. איך לא היה פחד אלהים לנגד עיני. ולא יגורתי מתוכחות על עון. ומן השפטים הרעים.

Now we will explain the principles of repentance. The first principle is regret: His heart should understand that leaving God is bad and bitter; and he should place into his heart that there is punishment, vengeance and repayment for iniquity. And he should regret his bad deeds and say in his heart, "What have I done? How did I not have fear of God in front of my eyes, and did not become afraid from the rebukes of iniquity and from the harsh judgments?

Now that we are within one week of Rosh Hashanah, it is worthwhile to talk about something that is both very important and mostly unknown. A great many of us have heard of תְּשׁוּבָה (teshuvah, repentance)—that is a word that is used a lot during this time of year. But relatively few have heard of חֲרָטָה (ḥaratah), which means regret.

Rabbi Yonah of Gerondi (bio) described regret as the first principle of repentance. Before one can repent for a sin, one first has to regret committing it in the first place. The reason is that regret is what prevents the High Holy Days from becoming a game. If we don’t feel remorse for what we’ve done, then the act of repenting for it becomes a holographic replica.

There is an ever-present danger that we will treat the laws of repentance like a game. People who game the system of Jewish law think they can recite the right prayers at the right time, say the right things to the right people, and walk out with a cleansed soul. The Mishnah (M. Yoma 8:9) anticipated this game long ago:

With regard to 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. Furthermore, for transgressions between a person and God, Yom Kippur atones; however, for transgressions between a person and another, Yom Kippur does not atone until he appeases the other person.

חֲרָטָה (ḥarata, regret) short-circuits the game because it ensures that one’s repentance will be authentic. Regret, of course, does not guarantee that we will not repeat the same sin later on. But it does assure that our act of repentance is the real McCoy.

There is an interesting connection between the word חֲרָטָה (ḥarata) and חֶרֶט (ḥeret). A חֶרֶט (ḥeret) is some kind of writing instrument, stylus, or script (see Isaiah 8:1). I think that חֲרָטָה (ḥarata, regret) is the חֶרֶט (ḥeret, writing instrument) of repentance. Now this connection is probably coincidental. Even so, I have found it to be a useful thought. Regret has a purpose, and its purpose is to make a record in our souls of our repentance.

Another reason for חֲרָטָה (ḥarata, regret) is that it replaces the old regime of biblical and rabbinic punishments for public transgressions. Back in the day, accidental sins required a sacrifice, while deliberate sinners were whipped or executed. Later on, Jewish courts punished sinners with fines, whipping, and, rarely, death. That system ended long ago, but the penalty of remorseful regret remains.

Regret occupies a middle ground between mere guilt, which may not be accompanied by a desire for change, and shame, which is destructive and cruel. Regret is the punishment that hurts us enough to encourage repentance but not enough to render us bitter and damaged.

You’re feeling bad about messing up? Good for you, and not in the Olivia Rodrigo sense! It is real progress to feel regret about a sin. It is that feeling of remorse that allows one to say, “I am a good person who did a bad thing.”

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Rabbi Eli Garfinkel is the spiritual leader of Temple Beth El in Somerset, New Jersey. He is the author of The JPS Jewish Heritage Torah Commentary.