I sit in my study late at night after breaking the fast of Yom Kippur. As I do every year, I feel euphoric. The day was so intense, we invested so much effort, and the Divine dividends that will be paid out over the year will surely be generous. We have been in repentance mode for forty days now and it is time to celebrate our successful effort.
Today we watched, through the portal of our imaginations, as the high priest strode into the Holy of Holies and offered incense. A cloud of steam filled the room and enveloped him. It was a time of awe and trembling as we chanted and prostrated in a state of deep contemplation. On Sukkot we will experience this cloud with palpable joy. It will be manifest in the sechach—the foliage canopy of the Sukah that will envelop us as we sit in the Sukah.
Sukkot will be our festival of joy. On Sukkot, we will celebrate the triumphant success of Yom Kippur. The forty days of repentance has paid off. Our slate has been wiped clean. We are now as innocent as newborns. Everything has been forgiven.
Let’s journey back to the Temple through the portal of our imaginations. This time we are there for Sukkot and are watching thousands of people stream up the Temple Mount and into the glorious Temple campus. The place is lit up. There is excitement in the air. There will be a celebration tonight and every other night of Sukkot.
The esteemed rabbis and leaders will dance and rejoice. The jugglers will perform. The people will sing and dance. Let’s listen to what they are saying: Ah, the righteous among them are thanking G-d that their younger years did not shame their older years. The penitents among them are thanking G-d that their older years atoned for their younger years. Oh quiet, it looks like both groups are about to join ranks and sing together. What are they going to sing? Ah, we can hear it now: “Praiseworthy are those who don’t sin, but if you sinned, repent and you will be forgiven.”
Wait, why are they talking about repentance? I thought we were done with that. It is after Yom Kippur, and we completed forty days of repentance. Why are they talking about it again?
The First To Sin
In the Midrash, we learn that the first day of Sukkot is the first day in the order of sins. The ordinary understanding is that we were given a new slate on Yom Kippur. No one sullied their slate between Yom Kippur and Sukkot because everyone was busy preparing for Sukkot and there was no time to sin. The first day of Sukkot is our first opportunity to relax. Hence it is the first day that we can possibly sin. Hence, a new account begins.
Well, perhaps that’s our answer. They are singing about repentance now because they need to address the new slate of sins that begins with the advent of Sukkot.
But wait, that can’t be the answer. It is only the first night of Sukkot. We have not even had a chance to enjoy our relaxed atmosphere. There have been no sins yet. And still, they are singing about repentance. What is that all about?
The answer can be found in a fascinating Talmudic tract. “Those who repent out of fear, transform their deliberate sins into inadvertent sins. Those who repent out of love, transform their deliberate sins into merits.”
I must admit that during the past forty days of repentance, my relationship with G-d felt a little fearful. There was distance between us, and I was desperate to bridge it. G-d was on His throne of judgment, and I pleaded for clemency. I repented, but it was out of fear.
Seeing the king from a distance, inspires awe and fear. Seeing the king up close and discovering that he is your father, inspires love. When we enter the Sukkah, we enter G-d’s loving embrace. It is the only Mitzvah into which we enter with our entire body, and it encompasses us fully. There is no other Mitzvah quite like it. When you are face to face with someone, you feel closeness. But when that someone throws their arms around you and embraces you, you are immersed in the closeness. There is nothing closer. Nothing more loving.
If the sechach canopy of the Sukkah represents the cloud of steam that arose from the high priest’s incense in the Holy of Holies, it is the highest representation of Divine intimacy. And this intimacy embraces us as we enter the Sukkah. We are fully in G-d’s embrace and are feeling His love. In return, we love Him too.
If that is the case, then indeed, now is the perfect time to repent. Until Yom Kippur, our repentance was born of distance and fear. We were triumphant on Yom Kippur and our deliberate sins were transformed into inadvertent errors and G-d forgave us. But on the first night of Sukkot, we have a new opportunity. Now that we are in G-d’s embrace and are feeling the love, we can transform our sins into merits.
This makes Sukkot the perfect time to repent. Notwithstanding the forty days of repentance and the forgiveness that we secured on Yom Kippur, we now have a chance to take it to the next level. By the time we finish the love fest called Sukkot, we won’t be forgiven sinners. We will be righteous people filled with newly transformed merits.
We now come to a new understanding of the Midrash that calls Sukkot the first day in the order of sins. The Midrash is not (just) saying that Sukkot is the first chance to commit new sins. The Midrash is saying that it is the first chance to transform our old sins into merits. This is why the righteous people and the penitents joined ranks on Sukkot and sang about repentance.
As Sukkot approaches, let’s prepare to immerse ourselves in G-d’s loving embrace. Let’s prepare for the ecstatic joy that arises from this embrace. And let’s resolve to channel this love and joy, into true repentance so that our intimacy with G-d won’t be one-sided. Not only will He embrace us with a true heart, we will also embrace Him with the fullness of our hearts too.