@dirge
I am not in a place where I can listen to the story, but I read the excerpts below and here are my preliminary thoughts.
"And then what I took home was a high level of shame because I walked in and I saw these people and say, you know what, wait. Their families are successful. Mine isn't. Does that mean that I am less than they are?"
-With all due respect, this is very much the human experience. This is how a very ugly person may feel in the presence of prettier people. This is how a fat person can feel in the presence of skinny people. This is how I - as a scientist - sometimes feel in a social sciences / economics setting.
I'm obviously not putting my feelings about that on the same level as this person's, but feeling "different" in some sense or another, even permanently, is just a part of the human experience.
Life is full of pain, full of disappointments, full of these small injustices like not getting a cab because you are black.
My advice to any kid in his position: be the best "prep school student" you can be and take the additional suffering being a poor black kid as a fact of life. Vindicate yourself by being the best, getting somewhere in life. There are black CEOs in America, top black scientists, hell, they have a black President. These are positions for which significant support among whites are crucial.
So hard it is, very hard it is even, impossible, it is not.