R’ Itzele Peterberger and the Alter of Slobodka, two illustrious students of Rav Yisrael Salanter, once discussed the custom to read Koheles during Chag HaSukkos. The morbid and fatalistic tone of Koheles, with verses such as, “Futility of futilities! All is futile!” and “I hated life, for I found evil in everything that occurs under the sun,” seem hardly appropriate to Sukkos, the Time of our Rejoicing.
R’ Itzele suggested that after we have resolved on Yom Kippur to abandon the transient pleasures of this world in favor of the eternal pleasures of Hashem’s service, we read Koheles to reassure ourselves that we have lost nothing in the bargain, since indeed the pleasures of this world are futile and unsatisfying.
The Alter suggested, alternatively, that we read Koheles to rejoice with the knowledge that even the futile pursuits of this world can be sanctified and elevated to the highest heights, when they are employed in the service of Hashem.
Both explanations give us deeper insight into the significance of Sukkos in general. The Gemara uses the expression תשבו כעין תדורו (“reside in the sukka as you would dwell in your home”) as the general rule of how we must spend the week of Sukkos:
כל שבעת הימים עושה אדם סוכתו קבע וביתו עראי כיצד היו לו כלים נאים מעלן לסוכה מצעות נאות מעלן לסוכה אוכל ושותה ומטייל בסוכה ומשנן בסוכה
For all seven days, man must make his sukka into his main place of residence, leaving his home peripheral. How so? He must move his fancy possessions and furniture into the sukka; eat and drink in the sukka; relax in the sukka; and study Torah in the sukka.
On the one hand, we leave our homes behind to show our disregard for the futile pleasures of this world, as R’ Itzele explained. On the other hand, as the Alter explained, we bring the comforts of our homes in to the sukka, to show that these same futilities can become a mitzva when utilized in the service of Hashem. Similarly, our mundane pursuits throughout the year, as petty as they may seem, really have great significance when viewed in the greater framework of a Torah lifestyle.
The Gemara further states that just as a sacrificial offering bears Hashem’s holy Name, so too do the walls of the sukka. The schach is compared to the wings of the Cherubim, which were stretched out over the Aron Kodesh. The holiness of the Beis HaMikdash flows into our sukka, imbuing it with the radiance of the Shechinah. It is amazing that the magnificent structure of marble and gold built by King Shlomo, wisest of all men, can be paralleled by our humble structures of wood and thatch. Yet this is the very segulah of Sukkos, to elevate all that is trivial and futile in Olam HaZeh by revealing the holiness of Hashem’s Presence which transcends all boundaries and exists in all places at all times.
Never was the joy of Sukkos revealed in greater measure than in the festivities of the Simchas Beis HaShoeiva that were conducted in the Beis HaMikdash on each night of Chol HaMoed Sukkos. These celebrations were held in honor of the water libations that were poured on the Mizbei’ach only during Sukkos, whereas wine libations alone were offered the rest of the year. The Gemara cites a source for these celebrations from the verse, “You shall draw water with joy from the wellsprings of salvation,” which implies that the joy of the water libations of Sukkos excelled the joy of the wine libations throughout the year.
In halacha, wine is considered the most distinguished of all drinks, while water is the most humble. Wine is the only drink that merits its own unique beracha; it is used, ideally, for the recitation of kiddush and havdala; and a beracha recited over it exempts all other drinks, since wine is considered ראש וראשון לכל המשקין (“the foremost, leading beverage”). Water, on the other hand, is such a simple drink that one would not even recite a beracha over its taste, unless he was thirsty. All other beverages, in contrast, require a beracha for their taste, even if one drinks them when he is not thirsty – to clear his throat for example.
Yet on Sukkos water is elevated to the level of wine, and both are poured onto the Mizbei’ach together. This also signifies the joy of Sukkos, as we have explained, when all that is mundane and futile is elevated to a level of transcendent holiness.
Another inference to this lesson can be drawn from the arava branch, which has no pleasant fragrance, bears no fruit, and thus represents the simple Jew who has no Torah study or mitzvos to his credit. On Sukkos, even he finds meaning in his life, as he joins together with the fragrant hadas (which represents the learned scholar), the fruit bearing lulav (which represents the mitzva performers), and the esrog (which has both advantages together).
Another insight into how the negative tone of Koheles fits with the joy of Sukkos can be found in light of the verse, “The lover of money will never be satisfied by money.” The more that a person is attracted to the fleeting pleasures of this world, the less are his chances of ever finding peace and happiness in this world or the next. “Envy is more painful than hell,” the verse states, and “Envy, desire and pride drive man from the world,” our Sages warn.
In the rat race to amass the meaningless trinkets with which we impress and compete with our neighbors, we lose all sense of appreciation for that which is truly beautiful and pleasing in life. This was precisely the sentiments of Shlomo HaMelech, who authored Koheles to bewail the disappointment, frustration, and futility of it all:
בניתי לי בתים נטעתי לי כרמים. עשיתי לי גנות ופרדסים ... כנסתי לי גם כסף וזהב וסגלת מלכים והמדינות עשיתי לי שרים ושרות ותענוגת בני האדם שדה ושדות. וגדלתי והוספתי מכל שהיה לפני בירושלם אף חכמתי עמדה לי. וכל אשר שאלו עיני לא אצלתי מהם לא מנעתי את לבי מכל שמחה כי לבי שמח מכל עמלי וזה היה חלקי מכל עמלי. ופניתי אני בכל מעשי שעשו ידי ובעמל שעמלתי לעשות והנה הכל הבל ורעות רוח ואין יתרון תחת השמש.
I built for myself houses and planted vineyards. I made gardens and orchards … I gathered silver, gold, and the treasures of kings and countries. I made musical instruments and all the luxuries known to man, with which I filled my chests and closets. I excelled all who had preceded me in Yerushalayim, while my intelligence stood by me. I denied myself nothing that my eyes desired, nor any enjoyment that my heart could fancy. My heart rejoiced from all my efforts, for this was my reward for all my labors. Then I turned to consider all that my hands had achieved, and all the fruits of my labors, and I saw that it was all futile, a vexation of spirit, with no benefit beneath the sun.
Many affluent businessmen can console themselves with the knowledge that they fell into the same snare that trapped Shlomo, wisest of all men, as they reach the height of their success only to finally realize that their fortune and all it has brought them are entirely futile and a vexation of spirit. They too must reach the same decision as did Shlomo, when he declared, “The conclusion of the matter, when all has been considered, is that man must fear G‑d and obey His commands, since that is the entirety of man.”
Only after man abandons his hope to find joy and satisfaction in the fleeting pleasures of this world, can he finally find the ultimate pleasure this world has to offer – which is the peace of mind brought by a humble, pure and holy lifestyle in the service of the Creator.
My rebbe and mentor, the Klausenberger Rav zt”l, would often quote his forebear, the Divrei Chaim of Tzanz zt”l, as having said, “I am nothing, I need nothing, and I demand nothing of anybody.” Such a sentiment might sound morbid and scary at first, but in truth this is the secret of perfect serenity. We were created with a duty of love to perform in the service of the Creator. We have no desire but to fulfill our duty and enjoy the sense of love and closeness to Hashem that this generates. Thus we can find happiness in whatever this world has to offer us, whether our portion in it is great or small.
סוף דבר הכל נשמע את האלהים ירא ואת מצותיו שמור כי זה כל האדם.
“The conclusion of the matter, when all has been considered, is that man must fear G‑d and obey His commands, since that is the entirety of man.”
 Sichos R’ Isaac Shor
 Sukka 28b
 Sukka 9a
 Sukka 5b
 Yeshaya 12:3; Sukka 48b
 Berachos 41, Rashi and Tosefos. Shulchan Aruch, Orach Chaim 174:2, Mishnah Berurah s.k. 2
 Berachos 43, Tosefos
 Koheles 5:9
 Shir HaShirim 8:6
 Pirkei Avos 4:23
 Koheles 2:4-11
 Koheles 12:13