From around the age 14 on, I got around this problem by wearing a hat nearly all the time. It didn't matter how long and gross my hair was. I just put on the hat and it looked just as good as any other day.
One of the biggest sacrifices I made in coming to work here was that the company doesn't allow me to wear a hat at work. (There's also a weird rule that men must wear long pants year round. Hot and annoying in the summer, yes, but not as bothersome as disallowing hats.) So now, instead of getting an annual haircut as I did in college, I'm forced to deal with the rats' nest on top of my head every couple months or so.
Thus far, the haircut experience in Korea has been refreshing. Since the hairdressers usually don't speak English very well, they don't waste their time trying to ask me about what I want done. I can say "cut. short." and they go about their business. It's quick and easy and costs less than $10. Far better than the one time I went to a barber in Boston, who dragged the process out telling me, "even if you don't care what your hair looks like, I do." He then charged $25 or some nonsense. I bought clippers the next day and avoided paying for haircuts for the next 3 years.
Tonight, however, was a reminder of everything I hate. A while back I moved, so the $10 place that was in my basement is now a bit of a walk. The past two times I have gone instead to a place across the street. It costs more like $15, but it's close and the hairdressers all dress in plaid skirt/school girl theme. I'm not sure why that is since most of their clientele appear to be women working the the night shift in the area, but whatever.
As per usual, I sit down say "I don't care. Cut it short." Or at least that's what I thought I said. However, the guy cutting my hair (he was not in a school girl outfit) seemed to hear, "please cut exactly 3mm off each of my hairs one at a time". After about 10 minutes and moving clips around on the back of my head and not seeming to do anything, I re-emphasize the 'short' concept.
Now, the thing that bothers me about this is not a language issue. Expressing the word 'short' is pretty easy. I both said it and demonstrated the appropriate length in universally recognized finger approximation. What bothers me, is that hairdressers would assume that I don't want them to cut much of my hair. As though, I want to maintain the gross blob of crap that currently resides on top of my head. THAT makes no sense to me. Why would I come in there if I didn't want my hair cut? Why is that an option that even occurs to hairdressers?
So, then the guy re-cuts the back of my head, and moves the the side where I can see what's going on and we repeat the process and I again request that he actually cut my hair. At this point, I realize I'm going to be here forever. Using clippers to buzz of the hair, like I would do, takes little time at all. Acting like my hair is a delicate masterpiece that must be carefully exhumed is incredibly tedious. I decide that I will just let the guy do whatever and not say anything since at this point I just want to leave.
He seemed to sense that I was unhappy and asked if I wanted it shorter. I told him I didn't care. I passed on the shampoo and was able to escape only having wasted 45 minutes of my life having little enough hair on top of my head cut that I will need to repeat the process in a week or so.
I think I might see if I can pull off a shaved head and save myself the hassle.