Should I cut my hair?

Okay, so I made a list of pros and I have about 25 reasons why I SHOULD cut my hair. The only reasons that I don't want to is because I'm scared that it won't look good and that I'll lose self confidence (which I barely have any of as it is) because I associate the only confidence that I have with my long hair and hiding behind it. I cut my hair once before (It was at its current length and I cut it to just below my ears and then grew it back out) and at first I loved it but then grew to hate it. I guess that it just depends on the person, but I'm not just not sure if I should do it. My best friend just cut 8 inches of her hair off after I told her that I wanted to cut mine (she didn't do it because of me, I just gave her the idea) and it's kind of giving me the bug to want to do it myself. So please, tell me if you think I should or not! It'll also take me about a year or so to grow it back out so keep that in mind too!