Yom Kippur is translated as the Day of Atonement. And what do we do on Yom Kippur? We confess our sins. Why do many feel uncomfortable with these words? Perhaps because they don’t sound so Jewish. Let’s try to clarify the proper Jewish understandings of many of the terms that are used at this time of year.

All for Us, Not for G-d

To begin this process, we need to go back to the very foundations of Jewish thought. As we have discussed previously, (in the article on Chosen People), since G-d is perfect and lacking nothing, the creation of the world cannot be in any way for G-d. It can’t be because, for example, G-d was bored, or curious, or lonely. The purpose must, therefore, be for the sake of the creation, and, most specifically, mankind.

That means that the mitzvot, the various dos and don’ts which G-d gave us to guide our lives, must also be exclusively for our benefit. How, then, should we feel if we transgressed any of them? We should feel that we ourselves missed out. This is surprisingly difficult for us to feel. How do we generally feel when we have transgressed? Guilty. To appreciate just how absurd this feeling of guilt is, imagine the following story.

Someone asks if he could borrow a valuable family heirloom of yours. You agree to lend it to him but caution him to be extremely careful, since it is irreplaceable. But then, through his gross negligence, he either loses or ruins it. How do we think this fellow will feel? Probably very guilty.

Now consider the same story with one important difference. There is a valuable family heirloom. And it is also lost or ruined through gross negligence. But in this second scenario, the heirloom does not belong to anyone else. The person ruined or lost his own family heirloom. He is certainly going to feel terrible, but it will be a different negative feeling. Now he will probably feel regret.

I want to suggest the following distinction between guilt and regret:

Guilt is the bad feeling we have when we let someone else down.
Regret is the bad feeling we have when we let ourselves down.

Now, let’s think how one that transgresses should feel. Logically, he should feel regret, since he let himself down. However, he is more likely to feel guilt. Why is this?

The Ironic Desire for Guilt

My Rosh Hayeshiva, Rav Noach Weinberg, zt”l, spoke about the ridiculous way that people relate to doing the right thing. We feel that somehow we are doing G-d a favor and helping Him out. Therefore, we tend to feel proud of ourselves when we do what is right, as opposed to simply feeling fortunate that we did what was beneficial for ourselves. He would, therefore, often remind us, when we did something good, to “take pleasure, not pride!”

Similarly, when we do the wrong thing, we usually feel guilt, as opposed to regret. As unpleasant as it may be to feel guilty in relation to G-d for what we did, there is also something ironically attractive about it. It helps us to maintain the illusion that we weren’t so stupid or self-destructive as to have directly damaged ourselves through the transgression that we did (even though, of course, that is exactly what we did do).

By the way, if the transgression involved hurting another person, then guilt, the bad feeling we have when we let someone else down, is obviously appropriate. It is only when the transgression primarily involved our relationship with G-d that guilt is illogical.

The Freewill Choice of Mitzvot vs. Transgressions

There are two fundamentally different ways to view avodat Hashem (serving G-d):

Torah perspective — Mitzvot are for our benefit and pleasure, while transgressions damage us and cause us to lose this benefit and pleasure. Our freewill choices are, therefore, between avodat Hashem (more benefit and pleasure) vs. transgressions (more damage and less pleasure).

General world perspective — Transgressions are a pleasure that, for some reason, G-d doesn’t allow us. Our freewill choices are, therefore, between avodat Hashem (less pleasure), and transgressions (more pleasure). As an example of this warped conflation of transgressions and pleasure, people will sometimes describe delicious food as – “sinfully good.” And there is even a type of tasty chocolate cake called “devil’s food cake.”

As a further illustration, a doctor tells his patient that he must stop smoking or he will suffer serious damage to his health. The patient sincerely promises the doctor that he will never smoke again. A few months later when they see each other, the patient apologizes profusely to the doctor and asks for his forgiveness — “I promised you that I would never smoke again, but I did. I really let you down. I’m so sorry.” The doctor is shocked at these words. He tells his patient — “I certainly do care about you and your health, and I am saddened that you have continued to smoke. But you obviously didn’t hurt me by continuing to smoke, you hurt only yourself!”

The Greatest Challenge of Teshuva

The Rambam discusses the essential steps of teshuva:

a. Azivat haChet — Abandon the transgression.
b. Kabala l’haba — Commit to never repeat the transgression in the future.
c. Charata — Regret having done the transgression.

In addition, the entire process must be verbally articulated (which is called viduy), and if the transgression involved another person, one must get forgiveness from that person.

Which is the most difficult part of teshuva? Most say it is the kabala l’haba, that one will never do this again. While a commitment to never ever repeat a transgression that one has stumbled in is indeed quite challenging, it may be that the charata (regret) is actually the hardest of all the steps. To understand why this is, we need to clarify the nature of charata.

The expression of charata in the Yom Kippur davening, as well as in the slichot (prayers for forgiveness) which we say throughout the year, is “v’lo shava lanu — and it was not worth it for us.” This seems to be a strange thing to say. Imagine a son that would tell his father — “Dad, I didn’t obey what you told me, and boy did I suffer!” It sounds like this son is not too concerned about having disobeyed his father. He is sorry only about the fact that his disobedience ended up hurting him. It wouldn’t make sense for this to be the attitude of a son when apologizing to his father. And it certainly can’t be how we should do teshuva and say viduy for having rebelled against G-d.

When we say the phrase “v’lo shava lanu — and it was not worth it for us” to G-d in our viduy, we don’t mean to say that we regret what we did only because it didn’t work out well for us. It is really just the opposite. In other words, it is specifically because we didn’t listen to G-d, whose only agenda was for our own benefit, that it necessarily didn’t work out well for us. Our regret should, therefore, be two-fold. First of all, we need to appreciate how terrible it was to have rebelled against G-d. But on top of that, we should recognize just how futile and misguided this was for ourselves personally.    

To honestly own up to this self-destructive impact of our transgressions, to accept both the responsibility for what we did as well as the destructive consequences that they caused, is, for many, the most challenging aspect of the entire teshuva process. However, once we have done this, the kabala l’haba (commitment for the future) becomes much easier. After all, we are then simply committing to stop hurting ourselves in the future.  

The problem with translating the Hebrew word “chet” (transgression) as a sin which would require atonement, is that it sounds like this is exclusively an issue of blasphemy or rebellion against G-d. While every transgression is indeed a rebellion against G-d, we must not lose sight of the massive damage that every chet also causes to us. By expressing the charata as “v’lo shava lanu — and it was not worth it for us,” the Rabbis are teaching us a critically important insight. The primary regret which we need to feel and articulate is for the damage that our transgressions caused to ourselves. And this awareness of personal damage is the most powerful safeguard to protect us from ever doing this transgression again. In other words, the charata (regret for having done the transgression through the awareness of just how much it damaged us) is what allows us to be able to make the kabala l’haba (commitment to never repeat the transgression in the future).

As an illustration of the facilitation which the charata (regret) performs for the kabala l’haba (commitment for the future), I know someone who was diagnosed with a serious medical condition which required her to drastically alter her diet. She is very picky, particularly when it comes to eating, and she travels very frequently. And yet, when she understood the necessity of this change for her very survival, she made the commitment to adopt it immediately. There is nothing like self-interest to motivate us to change.

Return to Reality

Teshuva happens to have a single-word English translation which expresses its essential meaning — “return.” The Talmud characterizes every chet (transgression) as a form of temporary insanity. We can see this in the common expression people use when apologizing – “I’m sorry. I just wasn’t being myself!” Teshuva is understood as a return – to reality, to ourselves, and to G-d.

Torah and mitzvot were given to us by G-d for our pleasure and benefit. This pleasure and benefit, however, takes effort which we are not always willing to invest. We need to view every transgression as a craziness, the primary damage of which is to ourselves. Teshuva is, therefore, simply the sensible process of working to regain our sanity and return to our real, healthy selves. We do this by abandoning our destructive mistakes, resolving never to repeat them, and regretting that we ever did them in the first place.

An ideal goal for Rosh HaShanah, whose purpose is to change the overall direction of our lives for the coming new year, as well as Yom Kippur, the day of spiritual rectification for our past mistakes, is to accept once and for all that G-d doesn’t need us for anything. He gave us the Torah and mitzvot exclusively for our own good, and when we aren’t strong enough, or sufficiently dedicated, to follow them — we hurt only ourselves. By committing ourselves to this awareness on Rosh HaShanah, or during the Ten days of Teshuva which lead up to Yom Kippur, then hopefully by Yom Kippur we will be able to fix up any mistakes we made this past year with a healthy regret, and without any negative guilt feelings.