A hole in a dream usually represents a difficult situation. If you are falling into a hole then you are getting into the unconscious side of your fears. That is, getting beneath the surface of your personality.
A hole above your head can signify a way through to spiritual understanding.
For some, a round hole in dreams is said to represent the Heavens and a square hole the Earth.
You could also be worried about digging yourself into a whole in your real life situation.