i don't know anything about portraiture, so i'm using your image to try to figure out what i think i would or wouldn't do in this situation, as well as what i notice and get out of your image.
this is really an interesting interpretation of portraiture. what i'm getting out of this is that one shouldn't be too quick to take the safe road, but instead, should be more willing to explore alternate routes for capturing the essence of the individual. thanks for sharing, and good luck!
this is a very interesting shot, but I think that the white border looks funny. I'm sure you're getting complaints about the grainyness of the photo, but I think that ti adds a lot of interest to the shot.