Eisav’s move was motivated by very practical considerations. He knew that the Land of Canaan had been promised to the descendants of Avraham, but it came with a price tag. Whoever would inherit the Promised Land would first pay off the “family debt”: G-d’s decree that Avraham’s descendants would be “strangers in a land that is not theirs” (Beraishis 15:13). In the words of Rashi (36:7), Eisav reasoned, “Let me move away from here. I will have a share neither in the gift nor in the payment of the debt.”

It seems, however, that instead of avoiding the debt by moving to Seir, Eisav could have paid the debt off with his move! G-d’s decree was that Avraham’s descendants would be “strangers in a land that is not theirs.” In what way was Eisav moving his entire family and fortune to Seir less payment of the debt than Yaakov’s family relocating to Egypt?

The answer lies in the word “strangers.” The debt that was left for Yaakov to pay was not that his family would be forced to journey from their homeland, as Eisav did, but that “גר יהי’ זרעך—your children will be strangers.” Eisav “settled on Mount Seir.” He wanted his children to have the comfort of blending in with their new neighbors and not remaining perpetual outsiders. Yaakov’s children would never become citizens in their host country; the payment of the family debt meant they would remain strangers and foreigners throughout their stay in the Land of Egypt.

The same is true of us, the descendants of Yaakov, during the current exile, the debt of which we will continue to pay until the coming of Moshiach. Maintaining our uneasiness and discomfort with the mentality and norms of exile is a virtue. We must anxiously await the Geulah, Redemption, when we will truly settle in the Land of Israel, finally collecting our long-awaited inheritance.

—Likkutei Sichos, vol. 10, p. 114

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