That depends on rather or not you are the type of person who prefers "low maintance hair" (like just pulling it up in a ponytail) or if you want something that you may absolutely have to wash and style every day and use product to achieve a cute short style...which is not really difficult, but it's not quite as easy as the ponytail.
I have done both and must admit that having a short haircut has always made me feel more "sassy" and longer hair usually makes me feel more "blah" and never really looks that great unless it takes me over an hour to make it look great.