The story of Joseph begins in parshat VaYeshev where his rise to power begins in a pit: They [Joseph’s brothers] took him and threw him into a pit (Genesis 27:31).
A short midrash explores the effect of this moment on the young Joseph:
They took him (vayikachu-hu) is written as though it could be read, he took him (vayikachey-hu). Now, who is the “he” among the brothers who might have thrown Joseph into that pit? It was Shimon, whom Joseph paid back when the brothers came to buy grain in Egypt and Joseph took Shimon from among them and imprisoned him (Genesis 42:24). (Click here for midrash in Hebrew and English)
In the hands of the midrash, a missing vowel reveals a drama hidden in the text—the story of a traumatized brother-now-a-prince who spent years imagining and then taking his revenge.
Scripture ultimately portrays a wise and settled Joseph who accepts the bruises of his fate as part of the divine plan to save his family and the world from famine. But perhaps Joseph’s acceptance appeared only when the fire of revenge burned away. According to the midrash, by the time that his brothers appeared in Egypt to buy grain, it had been years since Joseph had been in the pit. But when he met his brothers again, the pit was still in him.
The Israeli poet, Rivka Miriam, embellishes the theme:
I put on and stripped off the pit in turns.
Or, perhaps it was the pit that robed me and stripped me off.
I was crowned in its depths, blind in my shrouds.
And it was crowned in my depths.
Until crown made no difference.
Until it was never enough.
(Click here for Rivka Miriam’s poem in Hebrew and English)
Every word in Rivka’s first line appears in the story of Joseph, either when he is thrown into a pit by his brothers or when he is raised from one by Pharaoh. In not mentioning Joseph by name, the poet allows the pit to be our own.
Sicha - Continuing the Conversation 
Joseph was a lad of shining potential. His prophetic brilliance was so bright that it dazzled him, terrified his brothers and dismayed his parents. He only learned wisdom when he was stripped of his external honor and the depths of the pit enrobed him. As long as the pit remained within he he remained wise. The external honor of being raised up by Pharoah again robbed him of humility and he became again blind, robbing the poor to enrich the powerful.
Joseph’s late life teshuvah towards his family was the only thing that raised him up again. He needed to re-enter the pit to become wise. This was his teshuvah; his re-turning to his moment of humiliation and humility. Tragically, it was too late. He lost his opportunity to be a patriarch and even though his bones were returned to Canaan by the children of the children of his children. He final return to the pit was located in a place of great violence and inhumanity. Shechem. Nablus. His childred disappeared into the mists of history, consumed by the world of non-believers and cut-off from the God of Abraham, Isaac and Jacob.
Don Goldstein
If Joseph is an example of the tragedy of a missed opportunity, how much more can the same be said about Reuven? He saw that what his brothers were about to do went way beyond humbling a gifted but spoiled younger brother, but failed to act decisively to save Joseph. This failure of moral courage condemned one brother to “the pit” and cost the other his place in history.
But getting back to the main issue, I think that the point of the Rivka Miriam poem is that having “the pit” in or on us is not a good thing–humiliation has a way of leading not to humility, but to anger, resentment, and a desire for revenge. As a result, one could say that Joseph’s ability to reconcile with his brothers and see the larger (if not unmixed) good that came from the evil they did to him, came not from re-entering “the pit,” but from his ability to at least partially shed it.