Should I cut my hair? How to cut for maximum volume & definition?

I am still undecided on whether to cut my hair. I want to try something new and not use my hair as a safety blanket. However at the same time I have a round face and idk if it would look bigger with short hair. Also how do I get my hair cut for maximum volume and curlier curls? I have attached a pic of my hair, and another pic of how I'm hoping it'd turn out. Thanks!

This is what I want it to look like:

(the pic of my hair is attached)