I think everyone including me would feel quite stupid and angry when bitcoin reaches near $1000. Pretty sure at that point i would think why didnt i sell and go short.
Maybe you see things this way because you are a trader? I'm not a trader and I don't care that much. I've always wanted to have safe and anonymous money that I one day can use at stores. I still can't do it so I'm holding my coins and will hold them until it happens. If it never happens it's going to be sad, but it will mean that our society is not ready to be independent and we need others to dictate the pace.