When Jacob and Esau were children, they discovered their immense differences. Despite having the same parents and growing up in the same home, Jacob wanted one thing and Esau wanted another.

Jacob sought a life of meaning and fulfillment, a life he could look back on with a sense of achievement, knowing that he had done something to make the world better than he found it. What is the value of gems, comfort, leisure, and wealth if we have nothing meaningful to show for them at the end?

Esau was the opposite. He thrived on wealth, prestige, and power. He wanted as much of it as he could get and did not mind cutting corners to achieve his aims. If he had to steal from one, charm another, or even kill a third, Esau was prepared to do it. That was a price he was willing to pay for the glitter and glamour of wealth, power, and fame.

According to the Korban HeAni, the brothers understood that they were scions of the most important family on earth. G-d had chosen their grandfather and father before them, and the blessings of their ancestors would belong to them. They therefore divided their interests. Esau would take the physical wealth and material beauty of this world, while Jacob would take its spiritual gifts.

For a time, they followed their separate paths. Jacob left the land and stayed away for twenty-two years. During that time, Esau became increasingly wealthy and unruly, while Jacob lived modestly. He worked as a shepherd, married, raised a large family, and labored through heat and frost for his father-in-law.

Jacob’s New Perspective
Then everything changed. Jacob’s flocks multiplied, and he became a man of enormous wealth. When he returned to Israel, Esau was astonished. He had expected to meet a poor scholar, steeped in spirituality and academia. Instead, Jacob arrived with fabulous wealth.

Esau asked, “What is to you the great camp that I encountered?” (Genesis 33:8). In other words: How did you come to own so much? The deal was that you would leave the wealth to me. What do you need it for?

Jacob replied, “It is to find favor in my master’s eyes” (ibid.). On the simple level, Jacob was referring to Esau and hoping to mollify him with a generous gift. But there is a deeper meaning. Jacob was saying that he did not need the money for himself. His purpose was to use it in the service of his Master, G-d.

Until then, Jacob had thought that one could best serve G-d by living apart from wealth, without the distractions of luxury and comfort. But G-d taught Jacob something new. Wealth itself could become a spiritual tool. If a person does not become consumed by his wealth but sees it as a means of serving G-d, money can enable him to accomplish tremendous good.

Jackie Mason once joked that no Jew knows how to ride a boat. “A Jew doesn’t own a boat to ride it,” he quipped. “A Jew owns a boat to show it to you.” He was right, but only to a point. A Jew can own a boat to serve G-d with it. Wealth is not the problem. The question is what we do with it and where it stands in our lives.

Esau now suggested that Jacob and he travel together. All his life, Esau had viewed Jacob’s path as boring and had wanted nothing to do with it. He thought they had to travel separate paths: Esau with his materialism and Jacob with his spirituality. But now he discovered what seemed to him to be a better idea. Why not have both? He could serve G-d and enjoy life. Why not travel together?

Jacob refused. Although they now appeared to have something in common, they remained worlds apart. Jacob wanted to be with G-d and saw his wealth as a way to deepen that relationship. Esau wanted to enjoy life and saw a relationship with G-d as a way to enhance his material blessings.

This reminds me of a story about Rabbi Shlomo of Karlin. He was sitting with a fellow, and both took an apple from the table, recited a blessing, and took a bite. The fellow told the Rebbe that they were birds of a feather. Both had taken an apple, both had recited a blessing, and both had eaten it. The Rebbe replied, “You wanted the apple, and therefore recited a blessing. I wanted to bless G-d, and therefore ate the apple.” They did exactly the same thing, but they were worlds apart.

From the Clouds of Glory to the Sukkah
Our sages tell us that the purpose of sitting in the Sukkah is to remember the Clouds of Glory with which G-d protected us when we traveled through the desert. At first, the Jewish people needed that protection. They had left Egypt with enormous wealth. They had the means to pursue the pleasures of the material world and seek happiness in the watering holes of the wealthy.

So G-d enveloped them in a canopy of clouds. The clouds protected them from the elements, but according to our sages (Torat Moshe, Korban He’ani, and others), they also created a spiritual cocoon in which they could remain focused on G-d. At that stage of our development, we needed complete protection from the distractions of the material world.

Similarly, Sukkot is the festival of gathering. At this point in the year, our ancestors had gathered their harvest, their storehouses were full, and they had accumulated wealth. At precisely that moment, when material abundance was at its peak, G-d instructed us to leave our homes and enter a Sukkah.

The Sukkah is a place in which we are immersed in a Mitzvah. Our wealth remains outside, while we are surrounded by holiness; ensconced in a cocoon that shields us from the pitfalls of wealth.

But then comes the remarkable part: A Sukkah does not need to be completely enclosed. It can be kosher with only two full walls and part of a third. There are openings through which we can see the world outside, including our homes, our harvest, and our wealth.

Why the change? Because we have grown. The Jewish people in the desert needed the complete canopy (all four sides, above and below) of the Clouds of Glory. They needed to be fully shielded from the distracting glitter of the world around them so that they could establish their relationship with G-d.

But eventually, like Jacob, we learned that we do not need to escape material wealth and comfort to serve G-d. We can live among them without becoming consumed by them; be in the world but not of the world. We can sit with G-d in the Sukkah, look through its openings, see our wealth, and use it for G-d.

The message of Sukkot is therefore not that material pleasure is incompatible with spirituality, but that it is incomplete without spirituality. It must remain a tool but never become the purpose of our lives.

We sit in the Sukkah and leave our wealth outside. Our lives and our joy come from the Mitzvah; our wealth remains an accouterment, something we can use to serve G-d and accomplish great things. That is the perspective of Jacob.

Sukkot should never become a festival in which we sit outside amidst our accumulated wealth and peer into the Sukkah from the outside. We need not be completely cloistered from the material world. But we must know where we belong.

Perhaps this is why the Torah tells us that Esau went to Seir, whereas Jacob went to Sukkot (Genesis 33:16–17). They looked alike on the surface. They both had wealth. But they were still traveling on different paths.

Jacob went to Sukkot.