I also like the use of the cup, and how the pressure of other people's expectations is draining whatever you have in this cup.
I imagine this cup to be your happiness, your motivation. Perhaps even your confidence in yourself, and yet it seems to be other people that keep draining whatever you store up.
It reminded me also of the saying of glass half empty, or half full. And here is the battle of trying to make it full, but feeling it is always empty.