As you are ascending quikly in an elevator or in an airplane, would your eardrum tend to pop outward or inward?

When you are ascending, the air pressure around you is decreasing. Your ears "pop" (through the Eustachian Tube, not the eardrums) when the excess pressure behind the eardrum is released. However, before they do, your eardrums are under inner pressure and flex outwards a bit.