Should I cut my hair or not?

Leah • 21
I've been wanting to cut my hair since at least last year, but I've been really scared since my last hair cut was a disaster and I'm actually wanting to go shorter than last time! I just need a little bit of advice, so if anyone is willing to give some that would be great. :) Here are some pics of myself.
Now, I did NOT cut my hair, but I did pin it back to get the look that I want. Here it is.
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