Enjoy Sukkot; you earned it. You probably think you know what I mean. After the heavy lifting of Rosh Hashanah and Yom Kippur, the shofar, fasting, prayers, confessions, etc., we deserve a little relaxation and joy. But I am not talking about that. I am talking about something much deeper, so let’s dive in.
Many have asked why Sukkot appears after Yom Kippur in our calendar. After all, the sukkah—foliage-covered hut—symbolizes and celebrates the enclosed cloud canopy that G-d provided for our ancestors during their journey through the desert. If so, it should be celebrated after Passover, when we celebrate the exodus from Egypt. After all, it was from Egypt that our ancestors journeyed into the desert.
Many answers have been suggested over the years. One well-known answer is that Sukkot was meant to be celebrated in the Spring or Summer shortly after Passover. But since many people leave their homes and dine outdoors when the weather is warm, it would not have been evident that we were doing it for the Mitzvah. G-d, therefore, postponed it until this time of year.
While the answer explains why Sukkot occurs during the rainy season, it doesn’t explain why it is in such proximity to Rosh Hashanah and Yom Kippur. Is that just to bunch up the Jewish holidays?
The Kindness of Your Youth
To answer this question, we quote one of my favorite passages in the book of Jeremiah (2:2): “Go and call out to the ears of Jerusalem: I remember the kindness of your youth, the love of your nuptials; you followed me into a desert, an unsown land.”
Nearly a thousand years after our ancestors’ journey into the desert, G-d was still amazed by their trust. A people badgered and abused by their former cruel masters trusted G-d implicitly when He led them into a barren, lifeless desert. They never suspected that any harm might become them. They trusted G-d to protect them. Their trust pleased G-d so immensely, their love touched G-d so deeply, that He provided a cloud canopy to protect them from the harsh desert elements.
This canopy was not a benevolent gesture of unearned kindness. It was a well-earned reward. Our ancestors earned it on account of their trust. The Exodus from Egypt was not earned. The Jews did not deserve to be redeemed on account of their good deeds. They were saved because they were victims in need of saving. The canopy of clouds was different. This, they deserved.
Earned and Unearned
There is a huge difference between enjoying an unearned treat and one that we earn. When we do nothing to earn it, we feel a sense of shame for having something we did not work or pay for. It is human nature to earn our keep. There is an inbred sense of inadequacy that comes from being unable to fend for ourselves and being dependent on the largess of others.
There is also the sense of insecurity that comes from not knowing if we will have enough for tomorrow. Just because someone nice provided for us today doesn’t mean they will be there for us tomorrow.
When we have the means to earn our bread, we achieve a sense of dignity and security. There is no shame in earning such bread, and there is no fear about the future. Achieving this state of mind requires work, but the relief and dignity it brings are worth every effort. It brings great joy.
Timing of Sukkot
This offers a deep and rich insight into the timing of Sukkot. G-d provides for us throughout the year. Thank G-d most of us have roofs over our heads, clothing for our children, and food on our table. But there is always a nagging question in the back of our minds: do we do enough to deserve it?
I am not asking whether we work hard enough to earn our income. I am sure we do. I am asking whether we are good, moral, ethical, and holy enough to deserve G-d’s boundless blessings?
Think about how fortunate we are in this time and place. We live in an era of unprecedented freedom and prosperity. The size of a small home in North America was considered palatial when our ancestors arrived in Israel. The bounty and variety of our food were fit for a king’s table in ancient Israel. The availability of seasonal foods throughout the year was unheard of back then.
The convenience of purchasing ready-to-eat food in the supermarket or restaurant didn’t exist in the ancient world. If you wanted wine, you had to sow, plant, harvest, crush, ferment, store, and barrel. You didn’t just tap, Google Pay, or order it on Uber Eats.
We often take these conveniences for granted, but people who live in other parts of the world do not. It is why there is a never-ending stream of people trying to enter the United States through its porous southern border. Who would not want to get in and partake in such a luxurious lifestyle?
All this leaves us with a question: do we deserve all this largess? Yes, we work hard for our keep, but so does the poor farmer in Bangladesh. Yet, he earns a lot less buck for his bang. This nagging feeling of unworthiness spurs us to share some of our bounty with those who have less, but that doesn’t render us deserving of the rest. Today, we are talking about a nagging feeling that we don’t deserve any of it.
Days of Judgement and Atonement
These feelings humble us as we stand before G-d on Rosh Hashanah, the day of judgement, and Yom Kippur, the day of atonement. On Rosh Hashanah, G-d determines just how much we deserve and how much we earn. On Yom Kippur, G-d annuls and atones for our sins and shortcomings in the past year.
After these days, a huge stone rolls off our chest, and we know that what we earned last year was deserved. We stood before G-d in judgment and were found worthy in His eyes. If we had shortcomings, G-d wiped them clean on Yom Kippur.
Coming out of Yom Kippur, all the nagging insecurities and shame disappear. They are replaced by a palpable sense of joy and cheer. We have been vindicated. We have been found righteous before G-d. What we have, we have earned. We can enjoy it. Thus, we celebrate Sukkot with a hut that symbolizes the cloud canopy that our ancestors earned. That was the first Divine reward that we earned as a nation. This makes it an appropriate celebration for this time of year.
In other words, Sukkot is a celebration of life. We rejoice over every gift, every happiness, every earning, every good experience of the past year. We are grateful for it, and we are relieved that we can enjoy it with dignity in G-d’s eyes.
 Rabbi Yaakov Baal Haturim, Orach Chayim chapter 625.
 Nevertheless, we are taught that the righteous never demand their fair share from G-d. They always throw themselves on G-d’s mercy. First, they do all that they can to earn their blessings, then they beg for mercy. It is better to receive with humility from G-d’s loving Hand than to make demands on G-d from a place of justice.
 This essay is based on Rabbi Yehudah Aryeh Leib Alter of Gur, Sefat Emet, Sukkot, 56637.