In 20 years the struggles that every self-portrait artist has to face will still be extremely prevalent. The main struggle of a self-portrait artist is the struggle of how to distill a person’s essence into a short piece. No matter the medium and no matter the time, this will always be the primary struggle of the self-portrait artist.
I imagine that because the idea of “self” and “individuality” is growing increasingly distinctive that the idea of the self-portrait will become more appealing. The rise of vlogs indicate that people enjoy profiling their lives to the wider public. See popular vlog, Jenna Marbles: http://www.youtube.com/user/JennaMarbles, and like http://www.youtube.com/user/thecomputernerd01, or things like one photo every day for 6 years: http://www.youtube.com/watch?v=6B26asyGKDo.
I think that in the future, the “artsy” self-portrait might be extinct because nobody wants to hear someone talk about themselves – they want to see how this person might relate to them. So I think self-portraits will become more like vlogs: more informal and conversational. I frankly agree. I think that the traditional self-portraits don’t connect enough with their audiences and I would like to see more interaction going on. I think a cool video with lots of interaction, this one: http://vimeo.com/61434, where the author has someone else ask her questions instead of her asking the questions.
Honestly, the self-portrait genre will still probably be a popular assignment for class or for admissions. However, I think that more creative approaches will be needed to catch the viewers’ attention. I would love to see more reenactments in “self-portrait” videos so there is more action, rather than just scenes and images. I would also like to see more of a story line in “self-portrait” videos because stories always catch peoples’ attention and give them a reason why your life matters to them.