Why are we instructed to construct sukkot (huts or booths) for Sukkot? The Torah tells us that it is in commemoration of the sukkot we dwelled in on our way from Egypt to the Land of Israel.
(מב) בַּסֻּכֹּ֥ת תֵּשְׁב֖וּ שִׁבְעַ֣ת יָמִ֑ים כָּל־הָֽאֶזְרָח֙ בְּיִשְׂרָאֵ֔ל יֵשְׁב֖וּ בַּסֻּכֹּֽת׃ (מג) לְמַעַן֮ יֵדְע֣וּ דֹרֹֽתֵיכֶם֒ כִּ֣י בַסֻּכּ֗וֹת הוֹשַׁ֙בְתִּי֙ אֶת־בְּנֵ֣י יִשְׂרָאֵ֔ל בְּהוֹצִיאִ֥י אוֹתָ֖ם מֵאֶ֣רֶץ מִצְרָ֑יִם אֲנִ֖י ה' אֱלֹקֵיכֶֽם׃
(42) You shall live in booths seven days; all citizens in Israel shall live in booths, (43) in order that future generations may know that I made B'nai Yisrael live in booths (sukkot) when I brought them out of the land of Egypt, I the Eternal your God.
There's one problem though:
In the four books of the Torah that describe B'nai Yisrael living at various locations in the wilderness, there is not one other verse that mentions them living in sukkot. (The count of the number of times the books mention us living in tents would take too long. It's a lot of times.)
The Gemara, edited and compiled around 500 CE, records a discussion and disagreement on the nature of just what the actual "sukkot" in the wilderness were:
הניחא למ"ד ענני כבוד היו אלא למ"ד סוכות ממש עשו להם מאי איכא למימר דתניא (ויקרא כג, מג) כי בסוכות הושבתי את בני ישראל ענני כבוד היו דברי ר' אליעזר ר"ע אומר סוכות ממש עשו להם
The Gemara asks: This works out well according to the one who said that the sukkot mentioned in the [above] verse were Clouds of Glory, as it is reasonable that the roofing of the sukka is modeled after clouds. However, according to the one who said that the B'nai Yisrael made for themselves actual sukkot in the desert, and the sukkot of today commemorate those, what can be said? According to that opinion, there is no connection between a sukka and the Clouds of Glory. As it is taught in a baraita that the verse states: “I made the children of Israel to reside in sukkot” (Leviticus 23:43); these were the Clouds of Glory, this is the statement of Rabbi Eliezer. Rabbi Akiva says: They made for themselves actual sukkot.
In classic Talmudic fashion, now we have two opinions and no conclusion.
Does a sukkah commemorate the literal booths or huts B'nai Yisrael lived in in the wilderness? Or does it commemorate the Clouds of Glory, the divine clouds that sheltered them during those forty years?
Also in classic rabbinic fashion, it's probably both!
But what is the point of remembering what it was like to live in booths or huts? What is the point of remembering being sheltered by God's cloud? Do we really need both understandings? Why not just pick one?
What does each interpretation represent?
The "sukkah mamash," the real, literal booth or hut, is a temporary dwelling. It doesn't have four walls (or at least not walls that are substantial in any way) or a fully covered roof that would keep out the elements. It is easily taken down and easily put back up, good for traveling from location to location. It doesn't offer true shelter or security and anyone who has spent the holiday in a sukkah knows its inconveniences well.
When you dwell in a sukkah, you're far more subject to nature's whims. At its essence, to spend time in a literal sukkah is to embrace your own vulnerability. It is a statement that rejects the fallacy that you have full control, and that one must learn to live in flexibility and fluidity.
To point back to my remarks on Yom Kippur, it is about living in certain uncertainty.
The Clouds of Glory on the other hand...
If the sukkah mamash, the actual booth or hut, is a rejection of shelter, the Divine cloud is the ultimate shelter. B'nai Yisrael were safe in the wilderness, a place where they should have been most vulnerable, because they were under God's direct protection. God's cloud shielded them from the elements in a way a sukkah never could, and even defended them from enemies when actual sukkot are easily destroyed.
So for the true meaning of Sukkot to be clear, we need both Rabbi Akiva and Rabbi Eliezer. Sukkot are not just about embracing our vulnerability. And it's not just about remembering divine protection.
It's about a recognition that as human beings, we never have the power to be in complete control of our lives. But that if we surrender our need to be in control, there maybe someone else out there taking care of us.
So relax. Let go a little and revel in your insecurity! It's zeman simchatenu, the time of our joy! A little vulnerability can be a beautiful thing.