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I really wanted to post something cool tonight as an OP. But I couldn't think of anything, and all my files were sort of empty of anything original.
But you posted right about the same time, and I figured this was as good an opportunity as any to get something to DU that had some thought as part of it.
I remember a scholarship interview I had when I was a high-school senior. The question (from a professor I came to adore, but who at the time was just another scary university guy asking me questions) was, "If you could have dinner with any historical figure, who would you choose, and why?"
I chose William Shakespeare, because he was the writer I most recently studied, and whom I could talk most fluidly about (and whom I could dangle more prepositions near). I talked my way through the answer and could tell that I impressed no one.
Later, I wondered if I could have answered the question better with a different historical person, and I tossed around several possibilities in my head. Some worked out OK, some not so much.
I received the scholarship results in the mail and failed to get the prize, but I did get a secondary scholarship from that school. I always figured it was that single answer that cost me, and it haunted my thoughts for a while.
In time, I realized that the best answer was strictly non-academic, and I would have proven myself a much better applicant if I had thought non-linearly.
At this point, twenty years down the line, my answer to the question of who, out of everyone of all time, I'd most like to have dinner with would be: "They say that, at some point in time, there is someone exactly like you who has lived somewhere in the world. I would most like to have dinner with that version of myself, because it would provide me a chance to see myself as others see me. I trust in my ability to analyze others from many perspectives, but to analyze oneself from within is extremely difficult and subject to far too much favoritism. I'd love to have the chance to judge my own character from without, just as the world can do every day."
So my answer is, to overuse a phrase, "think outside the box."
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