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My PS starts as follows:

Booker Washington once said “Success is to be measured not so much by the position that one has reached in life as by the obstacles which he has overcome while trying to succeed”. While I reflect upon my life through the lens of Booker Washington’s wisdom, I feel a great sense of accomplishment. My quest for knowledge has endured through a succession of extraordinary obstacles, which should be considered when evaluating my position.

I know that many people say that it is a bad idea to start with a quote, but i believe that this quote fits directly into my entire story. If i was to cut the quote i would feel pressured to say something that is essentially identical to the quote. Obviously, i like my essay the way it is. My question is; is it a bad idea?

IMHO, using an opening quote is always a bad idea and for one simple reason: attention getter. You want your first line to draw your reader in. To me, all this quote is saying is that you are going to talk about how you have struggled in your life and how you overcame those struggles. How original.

I think I already commented on this, but drop the quote. Booker T. wasn't speaking to you directly, he was making a generalization about life that's pretty banal at this point. We can all agree that overcoming challenging situations is a measure of your success as a person. Don't waste precious space on a truism.

Starting or ending with a quote is the most cliché thing you can do. Avoid doing it at all costs.