If someone asked you to close your eyes and they said the words Yom Kippur into your ear, I think the visceral (that's fancy for gut) reaction would be dread. I don't think that's the original intention of the Torah. I believe that the Torah's position on Yom Kippur is that it should be a day of relief rather than anxiety. After all God tells us, “That on the very day I will forgive you for all your sins (Leviticus 16:30).” However, I believe that I understand the confusion. First of all many moderns have trouble fasting. Not that long ago Mother Hubbard moments of bare cupboards were common. So, until recently going a day without food wasn't only easier, it was frequent. I think that part of the problem is caused by the traditions as well. Even though the Talmud (Ta'anit 30b) is clear that Yom Kippur is the greatest of joyous festivals, because we are granted forgiveness and the second tablets were issued, our prayers give a different picture. We have those dismal chants about who will live and who will die and then we have TMI (too much information) about the grisly details of how death might appear. Then in the Musaf service after the happy description of the Cohen Gadol emerging gloriously from Holy of Holies, we read the gruesome description of the Ten Martyrs. Therefore, I understand the common Jew's confusion. It gets worse, because part of the reason for this discrepancy is built into the system, as you'll see.
There seem to be two scenarios of Yom Kippur's position in the repentance process. There are Midrashic sources which explain that the Teshuva (repentance) season continues until Hoshana Raba (the seventh day of Sukkot), therefore we don't sense the relief of closure on Yom Kippur. On the other hand Maimonides (especially in the first two chapters of his Laws of Repentance) explains that there are four periods of repentance: Rosh Hashanah, the Ten Days of Repentance, Yom Kippur, and the rest of the year. Clearly he is stating that the repentance and judgment period culminates in Yom Kippur, no role for Hoshana Raba. I'd like to propose a way of reconciling these inconsistencies.
The germ of my idea for solving this conundrum was sparked by an article by Dr. Meir Seidler on the Bar Ilan University web site. I hope I'll be forgiven for taking the concept in a totally different direction than the good professor. We understand that transgressions of societal norms can be describes as either crimes or sins. Crimes, which the modern world is much more comfortable with, require some compensation to an injured party, either a human or God. Sins are a spiritual category, which don't necessarily have a victim. Most of the damage from sin affects the perpetrator. Maimonides seems to be discussing crimes in his first two chapters of Laws of Repentance because he requires specific confession of acts followed by direct restitution or pardon for the explicit deeds. Later in his majestic seventh chapter, he presents a different picture. Maimonides says: Do not think that repentance is only for sins which involve an action, sins such as adultery, theft and robbery, but just as one has to repent if one committed such sins, so also does one have to seek out one's bad characteristics and abandon [those such as] anger, hatred, jealousy, cynicism, financial greed, honor, megalomania and similar characteristics - one has to return in repentance from all of these (7:3). This character development is about sins and the deleterious affect on one's soul and psyche.
Crime by its nature is about punishment and protection for victims, both past and future. The fallout from crime is relatively easy to measure. The spiritual impact of sin is much more difficult to calculate. Along comes Yom Kippur, and God proclaims to Moshe at Mt. Sinai on the very day the sin of the Golden Calf is forgiven: And the Lord passed before him and proclaimed: Lord, Lord, benevolent God, Who is compassionate and gracious, slow to anger and abundant in loving kindness and truth, preserving loving kindness for thousands, forgiving iniquity, rebellion, sin, and cleanses (Exodus 34:6 & 7). Yom Kippur is the trip to the cleansing bath. All the debt to society and heaven has been cleared from the ledger. But what about the damage to me?
Many criminals who have done their time or paid their price still carry a heavy burden of guilt. What can restore the dignity to the perpetrator? That's where Sukkot comes in. The only cure for the banishment that comes in crime's wake is reacceptance into the bosom of society. I can only think of Jean Val Jean carrying his yellow passport after serving a decade for stealing a loaf of bread. What can be done to make the former felon feel welcome again? I say this with trepidation because certain crimes have to be dealt with extreme care (especially drugs and sex offenders). However, for our theoretical scenario we will assume true regret over the past deeds, and resolve for the future not to relapse. Then there is no cure for the isolation felt by the outcast except loving embrace. Again remember Les Miserables. The local priest who accepts Jean Val Jean without reserve or precondition, changes our hero’s life. This love is felt in the sukkah. When we sit in the shade of our sukkah, we are reabsorbed into the bosom of our God. In mystical literature this phenomenon is the called the Shade of Faith (tzila d’mehemnusa). Normally, this is viewed as our faith in God, but equally it’s a show of confidence in us. So, for crimes Yom Kippur accomplishes the necessary cleansing, but for the sins we require the healing engendered by the Sukkot joy.
If crime requires punishment, then sin calls for rehabilitation. That reinstatement is completed only at Hoshana Raba, the end of the Sukkot festival. So, please, on Yom Kippur work hard to remember and regret any crimes you’ve committed, but understand that you won’t feel truly reintegrated into God’s embrace until you sit in the sukkah. Have a meaningful fast, and spiritual year.