1. Two kinds of repentance
The gemara (Yoma 86) tells us that there are two types of repentance – from love and from fear. It further explains that the effect of repentance from love is greater than repentance from fear: through repentance from love, intentional sins are transformed into merits, not just into unintentional sins.
While this source is well known, it is not so clear what it actually means. Does repentance from fear mean from fear of punishment, or from awe at God's greatness (“yirat haromemut”)? Does repentance from love mean from enjoying the performance of mitzvot, or from recognizing them as intrinsically worth doing? And what is the link between these terms and the repentance's resulting effect on your sin? And which explanation actually corresponds to what you experience while repenting?
Literally, teshuva means to “return” - to move from one place to a certain other place (where one has previously been). The “places” in this context refer to states of moral behavior. You start out as a person who commits a certain sin, and hopefully end up in a different state, of being a person who does not commit that sin. The process of teshuva is therefore that of becoming a person who will not commit the sin.
There are two ways, I think, in which this may be accomplished. You may decide not to commit the sin, and through constant self-control prevent the sin from repeating itself. Or else, you may lose the motivation to commit the sin. In my opinion, “repentance from fear” refers to the first type of change, and “repentance from love” to the second.
Based on this explanation, the gemara in Yoma 86 is easy to understand. A person is judged based on their character at the time of judgment. According to our explanation, if you repent out of “fear”, then the part of your mind which decided to sin no longer exists. So you are judged as if you sinned without deciding to sin: “intentional sins are transformed to unintentional sins”. But if you repent out of “love”, the original desire or urge which led you to sin no longer exists. Your character is that of a person who does good, and you are judged based on this: “intentional sins are transformed into merits”.
2. Two parts of Tishrei
This explanation of repentance may help us to answer several questions which arise regarding the holidays in Tishrei.
1. Of the two kinds of repentance (from love and from fear), which of them are we doing in Tishrei? Which type of repentance is the atmosphere of Yom Kippur, for example, designed to encourage?
2. The holidays in the Torah fall into two categories: 1) The pilgrimage holidays: Pesach, Sukkot, and Shavuot. 2) The holidays of Tishrei: Rosh Hashana, Yom Kippur, and Shemini Atzeret. These three are each one day long, are spaced about 10 days apart from each other, and all have the same set of musaf offerings, which is not offered on any other day of the year. These technical similarities suggest that the three Tishrei holidays (as well as Sukkot, which may be viewed as belonging to BOTH the categories of pilgrimage and Tishrei holidays) share a common purpose. But what is it? The commonalities between RH and YK are obvious. But what do Shemini Atzeret and Sukkot have in common with them?
3. The Mishna (Rosh Hashana 1:2) says we are judged regarding water on Sukkot. Thus Hoshana Rabbah is considered to be a solemn day of judgment, and we say special, very solemn prayers for rain on Shemini Atzeret. But doesn't all this solemnity contradict the idea that Sukkot and Shemini Atzeret are “zman simchatenu”?
Let us now try to answer these questions.
1,2. I think that in Tishrei we do both types of repentance – from love and fear – but on different days. On RH and YK and during selichot, the theme is repentance “from fear”. As explained previously, this means we make the decision not to sin. We search for negative character traits in ourselves, which manifest themselves in certain situations. We resolve to avoid those situations when they can be avoided, and restrain ourselves through self-control and increased motivation when they cannot. The major factors motivating this resolve include fear of punishment (and other fears, such as of not having lived a meaningful life, or of losing one's Jewish identity) – which is why this is called “repentance from fear”.
On Sukkot and Shemini Atzeret we also repent – but “from love”, not fear. Having just gone through RH and YK, we now have an exceptional degree of self-control and are avoiding many our the sins from the past year. But human nature is weak. We developed this self-control in response to the crisis of YK. But once the crisis passes, we very often relax and revert somewhat to our previous behavior. (For this reason, many people question the value of the repentance they do around YK – how can it be real repentance if the next year they'll be trying to repent for exactly the same thing?) To avoid this regression, on Sukkot we must “repent out of love” – that is, develop the good character traits which ensure that even in our “lazy” state we have no desire to sin.
The main tool we use for this is positive reinforcement. Sukkot and Shemini Atzeret are described in the prayers (unlike any other holidays) as “zman simchatenu”, and the celebration of Simchat Torah is scheduled for these days. Just after Yom Kippur, before our behavior has declined too much from its peak, we provide ourselves with as many happy experiences as possible. The goal is that we begin to associate our new, good behavior with these positive experiences. If we succeed at this, then our natural urge will be to do what is moral and correct, because it makes us happy. Even if our discipline level slips during the remainder of the year, we will still manage to avoid sin, because we no longer desire it.
This change can be illustrated with a metaphor. Behavioral decisions are like paths through high grass. If one path is commonly taken, it becomes worn down and more convenient to take in the future. To start on a new path, you must be willing to leave the old path and fight your way through the bushes. But each time you take the new path it becomes easier, and as you neglect the old path it becomes overgrown again. After Yom Kippur, having chosen a new path, we take these first few difficult trips through the bushes. The encouraging atmosphere of Sukkot gives us strength to continue with this, until the new path becomes more worn-down and convenient than the old one.
This “repentance through love”, through positive reinforcement, can only be performed after Yom Kippur. If we began the special repentance period with the happiness of Sukkot, then we would never get around to fully repenting. Certain necessary parts of the repentance process – for example, confession – are just not fun to do. Once we have gone through a traumatic period in which we take these steps and make these changes, we can take more pleasant steps which ensure that the changes become permanent.
3. The above analysis suggests that Sukkot and Shemini Atzeret are days of “repentance from love”, days of happiness, “zman simchatenu”. But this is not incompatible with their being days of judgment.
We normally associate judgment with beating one's chest, crying, and other unpleasant experiences. This is because judgment implies a deadline, before which we must make ourselves worthy of a positive judgment. Thus there is urgency and crisis. Unhappiness is a great stimulator of change, and with judgment approaching, we need change immediately.
But on Sukkot and Shemini Atzeret, we take a different approach to judgment. Yom Kippur is so recent that we (hopefully) are still on a spiritual high. In the short term, we cannot realistically hope to improve ourselves much more than we did in Yom Kippur. So the best strategy is not to begin an ambitious new repentance program, but to continue the path we decided for ourselves on Yom Kippur. And the most effective way to do this is to be happy, not sad.
Of course, judgment is still a time for seriousness, not frivolity. But a thoughtful person with self-control is capable of being both serious and happy simultaneously. (See
here for an argument that the difference between desirable happiness [“simcha”] and undesirable frivolity [“schok”] is the presence of composure and self-control.) By the end of Yom Kippur we have hopefully developed the qualities of thoughtfulness and self-control. In these circumstances, happiness on Sukkot contributes to our worthiness in judgment, rather than detracting from it.
At first glance the Shemini Atzeret prayer for rain, with its Yamim Noraim tune, appears not just serious but mournful. This fits so badly with the happiness of Sukkot that I suspect most of us either tune the prayer out, or pretend for a minute that it's Yom Kippur again. But if we see the prayers as both serious and happy simultaneously, there is no need for this cognitive dissonance. The prayer for rain is the moment at which we most directly confront the purpose of Sukkot (see Zechariah 14:16-17). If we are truly happy on Sukkot and not just frivolous, we should not see the prayer's serious tune (or content) as inappropriate for the emotions of the day.
3. One more implication
At the end of Musaf on Rosh Hashana and Yom Kippur, in the middle of the Sim Shalom blessing, we sing an alphabetical song which goes "Hayom ta'amtzenu, Hayom tevarchenu..." and so on, with an "amen" said after each phrase.
The first line of this song seems out of place to me. Translated, it means something like "May You give us courage/strength today". Why are we asking for this at the END of Musaf? The climax of the prayer service has passed and we are about to either eat lunch or take a two-hour snooze, depending on the day. Is this the moment at which we need courage and strength? Wouldn't this request be more intelligible at the beginning of Musaf, say, along with the chazzan's prayer before Kaddish?
This question arises from the assumption that when we finish RH and YK, we are finished with repentance. My suggestion is that at this point, we are only finished with ONE TYPE of repentance. As we finish this type, we begin another type. Along with a sense of accomplishment at having committed ourselves to a better way of life, we must understand the challenge of implementing our decision and making sure we live up to it. As we begin this equally large task, we ask God for help. The decisions we make ourselves; the implementation is mostly likely to succeed if God creates the correct circumstances for it.