Sukkot, unlike the rest of the pilgrimage festivals, does not commemorate any specific historical event. On Sukkot, we rather celebrate God's care for our ancestors by having them dwell in huts during their journey through the desert.
Why then do we not celebrate this festival in the month of Nisan? Does the Torah not say, "I made the children of Israel dwell in booths when I brought them out of Egypt"?
Perhaps the answer is that only someone who has gone through the experience of the Yamim Noraim, and embraced the spiritual values that emerge from them, can peacefully detach from comfort, leave their home, and live in a fragile Sukkah for seven days.
Sukkot is the opposite of Passover, exactly six months apart—Sukkot at the beginning of autumn, and Passover at the beginning of spring.
Sukkot, in a sense, is the "anti-Passover." And not just because it is on the opposite side of the Hebrew calendar. Passover is the festival of comfort. We place cushions behind us and eat while reclining; we treat each other as if we were royalty.
Sukkot is the complete opposite. We get our hands dirty building the Sukkah ourselves, we get wet (if it rains), we live for seven days without furniture or a solid home, and we give up the intimacy that our house provides.
Sukkot is the festival where we attach ourselves to the simple things in life, and even so, we practice joy, just as the Torah commands us: VeSamachta BeChagecha VeHayita Ach Sameach—"And you shall rejoice in your festival and be only happy." Sukkot teaches us that we are not defined by what we have.
An unfortunate popular saying goes: "Money doesn't buy happiness, but it helps." Many people live their lives by this phrase. They run anxiously after comfort and pleasures; they are slaves to consumerism and material ease. They find happiness in it, but their happiness is often just an optical illusion.
Sukkot comes to us every year with a message that is the opposite of that saying. Sukkot tells us: If you can be happy without money and without comfort, then you are doubly happy. Sukkot visits us each year with happiness in its most basic form. May God grant us the grace to experience it and to know how to appreciate it.
Chag Sameach, Moadim le Simcha ve Shabbat Shalom
Rabbi Gustavo Geier