Parashat Vayeshev tells the tragic story of mechirat Yosef – the brothers’ selling Yosef as a slave. They at first plotted to kill him, but eventually they decided to lift him from the pit into which they had thrown him, and sell him to merchants as a slave. These merchants then brought Yosef down to Egypt and sold him to a nobleman named Potifar.
The Midrash teaches us something very peculiar about this transaction. It tells that Yosef’s brothers used the money they received in exchange for Yosef to buy themselves shoes. This is the meaning of the pasuk in the Book of Amos (2:6) that speaks of a righteous person being sold for shoes: על מכרם בכסף צדיק ואביון בעבור נעליים. The Targum Yonatan writes that the צדיק mentioned in this pasuk is Yosef, whom the brothers sold in exchange for shoes, as they used the money they received to purchase shoes.
Why is it significant that the brothers bought shoes? Why do we need to be told this? What might the shoes symbolize?
After Adam and Havah’s sin in Gan Eden, Hashem told Adam, ארורה האדמה בעבורך, בעצבון תאכלנה – “The ground is cursed because of you; you shall eat it in sorrow” (Bereshit 3:17). Hashem placed a curse upon the earth, whereby earning a living will entail עצבון, aggravation and hard work. I do not know a single person, rich or struggling, whose livelihood does not entail challenges. This was Hashem’s decree after Adam’s sin – that making a living is going to be difficult. This is the curse declared upon the ground – ארורה האדמה.
Shoes have the effect of elevating a person from the ground. Symbolically, then, shoes allude to our ability to rise above the “curse,” the frustrations and hardships of life. Wearing shoes represents our refusal to get stuck in the “curse” that we’re struggling with, our determination to rise above it, to keep our heads held high, to see the blessing and opportunities in every situation, rather than wallow in paralyzing sorrow and despair.
This is why a mourner removes his shoes, and why we all remove our shoes on Tisha B’Av, when we all mourn the destruction of the Bet Ha’mikdash. During mourning, we are to fully feel and experience the “curse,” the pain and angst of what has been lost.
Conversely, kohanim did not wear shoes in the area of the Bet Ha’mikdash, because this territory is sacred ground, where there is no curse. For the same reason, we do not wear shoes on Yom Kippur, when we live a sacred existence, as though we return to Adam’s state before his sin, before the curse.
Nobody embodies the quality of rising above life’s curses than Yosef.
As a 17-year-old boy, he was betrayed by his own brothers, and brought to a foreign country as a slave. There he was tempted by his master’s wife, confronting the most difficult of all spiritual tests, and he prevailed. The Rabbis teach that Yosef’s triumph over the lure of immorality is what protected Am Yisrael throughout the 210 years they spent in Egypt, which was the most immoral society in the ancient world. Yosef’s strength and resolve set a precedent that kept our nation pure throughout the years of slavery in Egypt. Yosef rose above the “curse,” and transformed his personal challenges into a great achievement that ended up guaranteeing the nation’s spiritual survival.
This is why shoes are associated with mechirat Yosef. The brothers thought they were destroying Yosef, but he did not let himself be destroyed. He succeeded in lifting himself up, and using his tragic situation into an opportunity to achieve greatness.
This is an example for all of us to follow. We all face periods of עצבון, times of sorrow, pain, loss, frustration, and anguish. In the case of the passing of a loved one, Heaven forbid, halachah tells the mourner to remove his shoes, to focus on the void, on what has been lost, and on the pain. At other times, however, we are to “wear our shoes,” to rise above the “curse,” to not allow ourselves to get stuck in negativity. We, like Yosef, have the strength to grow from life’s challenges, to use our difficulties to lift us up and make us great.

