shucks pal I understand you asking- because yes, I had long hair for a long long time! I had it cut short first when I was, gosh, 13? maybe 14, and yes I was nervous! But I went for it, and it was okay for a week but I had it cut in a bob and didn’t know that a bob does not stay straight if you have curly/wavy hair and ended up looking like a fruzzy mushroom for months. I went back to being long haired for a while then went short-ish again in my late teens. I also didn’t know that you basically don’t brush hair like mine! It works best just leaving it be! It was all a learning experience though and I am very happy staying short haired forever- it’s very easy to maintain and never gets knotted!
Basically, if you’re getting it cut, regardless of it being short or mid-length, tailor it to the kind of hair you have! Not much use fighting nature, even if straighteners and curling tongs are a thing. If you have wavy/curly hair it will probably do the same as mine, but if it’s straight maybe try something like a pixie cut, or ask them to make it choppy and use some hair wax to muss it up. I’m no hair expert, but when it comes down to it the best way to style your hair is to cater to your hair.