Damned Designers?

I too am ridden with self-doubt; and not just with my designs. During crits is when the self-doubt butterflies come alive in my belly. Sometimes I’m afraid to comment on other's work because I think "what do I know?" I can't even get a handle on my own work much more feel qualified to comment on another’s. When and where is the point in a designer's career when the light bulb switches to "on" and we become confident with our decisions? I will work on a piece for what seems like years, be satisfied with my creation, then take it to class and get shot down in every way. I actually don't think there's ever been a situation when this has not been the result. I'm convinced there is no such thing as a great first idea because no project is the same from beginning to end.

A funny thing happened to me on Friday afternoon: I met with a recruiter and brought a few design samples for her to see. As she was flipping through the files she complimented me on my "edginess" but asked if I had anything more practical to show her. It caught me completely off-guard because I always prided myself on being "edgier." Apparently this is not marketable. The whole thing confused me to no end and I found myself drowning (again) in the pool of doubt (and maybe a little pity). Where is the line between being myself and being "marketable?" It seems like you’re damned if you do and damned if you don’t. If anyone has any advice on how to avoid feeling trapped between these two situations, I would love to hear your thoughts.