I was thinking of starting a thread with the same title! I’ve had long hair all my life, and the shortest I’ve ever had it cut was about shoulder blade length, until I went to a stylist about a week ago and forgot that you have to tell them you want your hair at least four inches longer than your actual minimum preference. My hair now just grazes my shoulders in what I think they call a “face-framing cut” but I think of as the local news anchor style, which can be more or less styled and a variety of lengths. It’s also layered a little, because it’s gotten kind of thin over the past five or ten years and the stylist thought it would look fuller (she was right). I also know myself, so I warned her that, no matter how much I might believe I’d do whatever magic a cut needed to make it look good, in reality I would just end up going out with wet hair and letting it dry as I drove to work, so it had to be very literally wash-and-go.
I’m amazed at how much I like it now. I keep on being surprised at my hair not being everywhere - I don’t roll over on it in bed, it doesn’t have to be hauled out of my shirt collars with large dramatic movements, I don’t have to be careful to keep it from dragging through my plate - I hadn’t realized it WAS in the way so much. And did you know you have to use WAY less conditioner on shorter hair? Weird. It also surprised me how much less time it takes to rinse, dry, and brush.
It sounds like you’ve done this before, so it won’t surprise you, of course. My advice for finding someone good to cut it is similar to everyone else’s - ask people whose hair looks good. Also, you can sometimes run across a great stylist at Supercuts, but I’ll reiterate that this is one area where you do tend to get what you pay for. Your odds are way better at a shop that charges more.