Look at a picture of a graduation cap (below). See how it's a square on top and circular at the bottom?

What it symbolizes is that your natural round head has become a different shape, a square, and you now think like everybody else: you've been brainwashed and your mind has been molded and it's now a square.

I don't think being a "square" means taking favorites or overs or favorite teams (when the time is right), I think it means that your thought process is like everybody else. You aren't "sharp" because you have no EDGE over the rest of the public because you're using the same data and methods that the rest of the public uses.

In order to become sharp you have to start thinking different, way "out of the box" (boxes are usually SQUARE), imho.