Welcome to Daily Bitachon and our final pre-Sukkot thought. As we all know and have mentioned before, our sukkah is a continuation of Yom Kippur, specifically in the realm of teshuvah. The Rambam, in the Laws of Teshuvah (2:4) and based on the Gemara in Rosh Hashanah 16b, outlines a sequence of steps to help a person achieve full teshuvah and kapparah. He concludes with the principle that one exiles himself, because exile brings atonement for sin by causing a person to become humble and low of spirit.
Sukkah as Exile and the Path to Humility
Humility leads directly to teshuvah. That is why the Pesikta DeRav Kahana teaches that Sukkot follows Yom Kippur: if exile was decreed upon us, dwelling in the sukkah serves as that exile. How does the sukkah accomplish this? Exile humbles us, and entering the sukkah instills that very humility.
That humility is our ultimate goal. Rabbeinu Yonah in Shaarei Teshuvah (1:23) writes that humility is one of the fundamentals of teshuvah, citing Tehillim 90:3: "Tashev enosh ad daka"—"You return man to the point of being crushed," meaning until he is truly humble. This process began on Rosh Hashanah; as the Gemara in Rosh Hashanah 26b notes, the bent shofar symbolizes a bent, humble posture. Our primary focus throughout this entire season has been cultivating humility.
On Rosh Hashanah, we emphasize humility. On Yom Kippur, fasting humbles us as we confront our frailty and powerlessness. The climax of Yom Kippur—Ne'ilah—centers on this realization: "Mah anu? Mah chayeinu?" What are we? What is our life? What is our strength? What is our power? Great leaders are as if they never existed, and the wise appear without wisdom. It is entirely about recognizing that we possess no independent power; we stand humbled before Hashem.
Now, with Hashem's help, we can connect this theme to Chag HaAsif—the Festival of Ingathering—which traditionally refers to harvesting our grain and produce.
The Furrows of Arrogance
Rav Yerucham often noted that one can study a negative trait and apply its inverse to the positive. Rabbeinu Yonah in Shaarei Teshuvah (1:27) explains that arrogance causes numerous sins and grants the yetzer hara the strength to overpower a person. He cites Devarim 8:14: "Your heart will become haughty, and you will forget Hashem your God." He also brings Mishlei 21:4: "Haughty eyes and an arrogant heart are the furrow (nir) of the wicked for sin."
What does this mean? Haughtiness functions like a furrow plowed by the wicked into their own hearts. Once someone adopts an arrogant mindset, sins take root and grow abundantly, just as crops thrive in the furrows of a plowed field. If a farmer sows an unplowed field, the seeds struggle to take root and yield a meager crop; but when the soil is well-plowed, seeds take root easily, producing a bountiful harvest. Rabbeinu Yonah is teaching us that the seeds of wrongdoing readily take root in a haughty heart and yield an abundance of sin. Those very same seeds of transgression would shrivel and die in a humble heart.
The Beit HaLevi opens his essay on humility by stating that haughtiness is among the most severe sins in the Torah, leading a person toward every possible evil. He quotes the Midrash (Bereishit Rabbah 22:6): when the yetzer hara sees an arrogant person, he says, "This one belongs to me."
Rabbeinu Yonah elaborates that just as a farmer plows furrows to produce an abundant yield and gather a large crop (le'esof rov tevuot), the wicked plow furrows of haughtiness to cultivate and gather sins. Notice his use of the root asifah (ingathering)—the exact terminology of Chag HaAsif.
Plowing the Heart for Teshuvah
In his commentary on Mishlei (21:4), Rabbeinu Yonah states what he said in Shaare Teshuvah and adds that this metaphor also works in the positive direction: a baal teshuvah must cultivate his heart for repentance. In Yirmiyahu 4:3, Hashem instructs the people of Yehudah and Yerushalayim: "Niru lachem nir ve'al tizre'u el kotzim"—"Plow for yourselves a furrow, and do not sow among thorns. Circumcise yourselves to Hashem, and remove the barriers of your hearts." (See Rabbenu Yonah Mishlei24:30 more at length)
Just as a farmer plows to soften the soil so seeds can take root, while uprooting thorns that would ruin the crop, a Jew must plow furrows in his heart. This allows the seeds of teshuvah to flourish while eliminating the destructive barriers of arrogance.
This brings us to our main point: throughout the Yamim Noraim, we plowed our hearts to cultivate humility. Our Sages teach: "Kol shanah sherashah bit'chilatah, mit'asheret besofah"—a year that begins poor and humble ends in spiritual wealth, echoing the verse "Tachanunim yedaber rash" (the poor man speaks with supplication).
After plowing our hearts, we arrived at Yom Kippur and planted the seeds of teshuvah—our positive commitments and resolutions for the new year. Miraculously, within just four days, a harvest begins to emerge. In many communities, the Yom Kippur liturgy around Kol Nidrei highlights the verse "Or zaru'a latzaddik u'leyishrei lev simchah"—light is sown for the righteous. On Rosh Hashanah, Hashem is our light (Hashem ori), and we sow those lights. These spiritual seeds sprout with extraordinary speed. Just as the Jewish people crossed the Jordan on the tenth of Nisan and miraculously harvested grain for the Korban HaOmer days later, Hashem fosters rapid growth in our hearts. By the time Sukkot arrives, we are ready for Chag HaAsif—the ingathering of the spiritual harvest cultivated within us.
The True Meaning of Chag HaAsif
The Rashbam (on Vayikra 23:43) explains why Sukkot occurs during this specific agricultural season. When a farmer gathers his grain into the silo, a natural sense of self-satisfaction and pride arises over his hard work and success. Hashem therefore commanded the mitzvah of sukkah to remind us that we once lived in the desert without permanent shelter, dwelling only in fragile booths. By reflecting on this, we recognize that every success is an unearned gift from Hashem, leading us to deep gratitude.
This timing directly counteracts the haughtiness that material prosperity often generates. The sukkah instills humility so that we do not become arrogant and forget our Creator. This also explains why Sukkot is celebrated in Tishrei rather than in Nisan, when the Clouds of Glory (Ananei HaKavod) first appeared: we need this specific lesson at harvest time.
In Moreh Nevuchim, the Rambam writes that Sukkot teaches us to remember difficult times while experiencing prosperity. This perspective inspires genuine gratitude and deepens humility. We leave our comfortable homes to dwell in temporary huts—just as our ancestors wandered in the wilderness—recalling our vulnerable beginnings. Any prosperity that followed was not achieved by our own power; it came through Hashem's kindness and the covenant He made with Avraham, Yitzchak, and Yaakov in honor of their righteousness. The Rambam notes that this is a foundational principle of the Torah: every blessing we receive comes through the merit of the Avot.
This is the deeper message of the season. Sukkot is about harvesting what we have cultivated. We are presented with two paths: we can plow the heart with arrogance, sowing sin and harvesting its consequences; or we can plow with humility, softening our hearts to receive the seeds of teshuvah and gathering the beautiful spiritual harvest of our mitzvot during this festival.