My hair was already very short when I starting cycling and I love it. Super convenient, and when I take my helment off, I can just run my fingers through my hair and I'm good to go (it also dries very fast). I know a lot of long hair peeps can do that too, but my hair is higher maintenance when its long. I wore it long for most of my life, but it always looked pretty cr@ppy after any athletic stuff.

I guess it just depends on your hair....