Wanted to update guys. Its cool to see this first post and remember the first day I did it.
Since shaving my head, I have gotten a new confidence. It took about 30 days (imagine that) and alot of trips here to read other people's advice to get cool with it and accept it. Now, I will never go back. I have also lost 27 pounds and am happier than ever.
So, if you are thinking of doing it. DO IT! Once you get a routine, and some sun on your head, you can't beat it.
--Josh