Here's a self-portrait from my high school years that I keep coming back to. I'd say it captures my awkward teenage years pretty well. The half-closed eye and bared teeth are interesting to me. I think they show both the depression and hostility I was grappling with at the time.
I know this may seem self-indulgent but I've always found I can never know what I'm going to end up drawing until it is done. Furthermore, the actual meaning of my artwork often eludes me since it undoubtedly dwells in my subconscious somewhere. Nevertheless, I like to attempt to examine where I've been in keeping with the whole "know thyself" thing.