All the Yom Tovim are times of simchah, but only Sukkos is referred as zman simchaseinu. The first night of Sukkos is my favorite night of the year – the one where my inner emotional state is most consonant with that commanded by the halachah. On leil Sukkot, the gashmius and ruchnios perfectly reinforce each other.
Assuming that it does not rain, the temperature is almost always perfect, neither too hot nor too cold. Our sukkah is large enough to hold our entire family and many guests comfortably, and with only a few lights illuminating the darkness, this is as close as we ever get to eating by candlelight.
The sukkah on the balcony immediately below ours belongs to a family of boys justly known for their beautiful harmonies. Usually, we hear no more than a few snatches of "Shalom Aleichem," as we walk up the stairs on Shabbos. But on Sukkos, we have a week of concertizing. On the other side of our apartment, our kitchen window is right above the sukkah of one of the most prolific composers in the Jewish world. So we are surrounded, on all sides, by concert quality singing and musicians.
In ancient times, when our ancestors farmed the land, Sukkos was a joyous time because it marked the end of the agricultural cycle. The farmer could contemplate his grain now safely stored for the winter with both satisfaction and gratitude. The satisfaction that comes from reaping the benefits of one's hard labor; the gratitude to Hashem for having caused the winds to blow and the rains to fall in their proper time so that all that work did not go for naught.
Most of us are no longer farmers, and our lives are only tangentially tied to the agricultural cycle of sowing, reaping, and gathering. But there is a spiritual parallel to the farmer's sense of well-being at the end of agricultural cycle.
We have been engaged in intense spiritual work for over a month. As we look back on our journey towards reconciliation and closeness with Hashem since Rosh Chodesh Elul, we experience on a spiritual level the same satisfaction and gratitude of the farmer reviewing his year.
Rosh Hashanah called upon us to contemplate the ideal tzuras ha'adam in accord with which Hashem created Adam HaRishon. In the process, we were forced to contemplate our own unique cheilek of that ideal – the special mission allotted to us in life.
With that clarified vision of whom we are meant to be to guide us, we were now in a position to examine our deeds and to consider how and why we have fallen short of our own ideal and failed to yet fulfill our particular mission. That is the process of teshuvah culminating on Yom Kippur.
We emerged from Yom Kippur, in Rabbi Yitzchak Hutner's unforgettable description, not a besser (better) person, but an andere (different) person. The Rambam describes the chasm between the person we were and the one who we become through teshuva: "Last night, he was hated before Hashem, disgusting, distant, and abominable. And today, he is beloved, a delight, intimate, a close friend" (Hilchos Teshuva 7:6).
On Yom Kippur, Moshe Rabbeinu, received the Second Luchos, and that giving of the Luchos is described as a marriage between Hashem and Klal Yisrael. While the wedding is the milestone that young couples most remember, it is only the beginning of the process of growing close and comfortable in one another's presence.
And so it was, with respect to the closeness of Hashem and Klal Yisrael. Only on Sukkos, five days after the chuppah of Yom Kippur, did the Clouds of Glory return. Only then was the reconciliation complete, and were we totally enveloped in Hashem's love.
When we leave our homes and enter into the temporary dwelling of the sukkah, we place ourselves directly under Hashem's protection, just as our ancestors did in a howling desert, and we experience His closeness, just as they did.
THERE IS YET ANOTHER ASPECT to the rejoicing of Sukkos. "Who is a happy man?" ask Chazal. And they answer, "One who is content with his portion." That is a very high spiritual level, especially when so many in our world are struggling to provide even the basic necessities of life.
Only one who views the world through spiritual glasses, not material ones, can be content with his portion. As long as a person's focus is on the material, he will always perceive himself as in competition with everyone else over a limited pie. Envy, desire, and the pursuit of honor will be his constant companions.
The move to an impermanent dwelling facilitates what Rav Dessler calls bitul hayesh – the negation of our attachment to the physical world. To the extent we succeed in turning our focus from the physical to the spiritual, life ceases to be a zero-sum game of endless competition. The spiritual world is infinite. One Jew's spiritual growth is never at the expense of another; indeed it only makes more likely others' spiritual growth.
In the spiritual realm, all Jews can come together as brothers, not competitors. Every night in our prayers, we express the intrinsic relation between the sukkah and peace when we request Hashem to "spread over us Your sukkah of peace."
Galus, the loss of a permanent home, is not just the punishment for sinas chinam, it is part of the cure. Galus increases our feeling of dependence on Hashem, and lessens our attachment to the physical world. And so too does living in a impermanent dwelling for the week of sukkos pave the way for greater unity among Jews by lessening our attachment to physicality.
The ultimate expression of Jewish unity was the rejoicing of the Simchas Beis HaShoeva when the Beis HaMikdash still stood: One who never witnessed the rejoicing of Simchat Beis HaShoeva, say Chazal, never saw true rejoicing. Even today, we can still taste that unity at a large simchas beis hashoeva, with thousands wending their way around the room hand in hand, shoulder to shoulder melding into one.