I think it's partly being taught not to be assertive (at least in my case), feeling some intimidation when confronted by a "specialist," and sometimes, being confused as to what we do want or how to ask for it. It's hard to go into a salon and say, "I want XYZ and nothing else." A good stylist should be willing to ask and guide, though.
When I went in for my curly cut a few weeks ago, I was really anxious for a lot of reasons: 1) Stylist was a man, and men I don't know intimidate me; 2) He's the salon owner, so even more intimidating; 3) I have old henna on my ends, and most stylists freak over henna; 4) I've been trimming myself for four years; 5) I just kind of chopped in a little bit of face framing hair so I could see if I didn't mind hair in my face; 6) I'm just a middle-aged housewife, a bit dowdy. I pictured all sorts of scenarios, most of which ended with me being embarrassed, never going back, and getting a bad cut.
But he was actually really good. He asked about the old color, but didn't bat an eye at the henna. Said it made sense when I told him about the face framing bits, and didn't say anything about my hair being wildly uneven. He was very casual, which helped my anxiety a lot. And he explained everything he was doing. We talked about how much I wanted off and he made sure I understood the difference between straight length and curly length. Then he cut, showed me how much, and asked if I wanted more off When he washed and styled it, he explained what he was using and how to use it, how to clip, etc. I've never had a stylist be that accommodating in terms of just making sure I could recreate the look at home (more or less, haha).
My only regret is that I didn't go shorter. I've lived with it for three weeks now and I think I'll go in next week and have another four inches taken off. It'll cost me another $80 (that's including tip, for two hours in the salon!), but it's worth it because I like to be sure before I cut, and I've already cut a good 18" since about March.
Former longhair, now CG, living in N. California where the fog meets the wind
3a/b, fine, normal porosity/elasticity, high density
Conditioner wash and style, sometimes with a dab of BRHG.