I cut it short (an inch or two above my shoulder... so kind of a long bob) a little over a year ago. it was an adjustment but i loved it haha. it took a year to grow back out and I'll probably wear my hair long for a while. I might cut it short again at some point though.
I worked up to it though. I had been thinking about cutting it short for a while. I cut my hair every 6-8 months so every time that I went to get it cut, I got it cut a tiny bit shorter than the last time. So the time before I cut it "short" I cut it maybe an inch below my shoulder and got used to it like that. So when I went to get it cut again months later I just went for it haha.