The first time I cut my hair short, I didn't cut it -- I shaved it. Completely. Bald. Right down to the skin. I raised money and donated to the Stollery CHildren's Hospital. Ends up I love my hair short -- so much easier to deal with, and much cooler in the summer!!
It was dramatic, yep, and I was hesitant the first time I did it. But the thing to remember is it's just hair, and it grows back. Eat lots of jello, and it'll grow back faster (Jello is also good for your nails).
Hair isn't part of your identity, unless you have something living in it. It doesn't define you as a person, and it won't change you as one if you decide to cut it. If you loved your hair for what it was, I'd encourage you keeping it -- but it sounds like you hate it and only keep it because you should. I say go for a change. It feels good to give things a try now and again, and if you end up hating it, let it grow out again.
Big word of advice, though -- don't just get it chopped. Get a hair cut by a professional or you may end up hating the style you get!
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