After talking with a few teachers how have been working in secondary classrooms there are a couple conclusions that are pretty solid. One, you have to be tough. Especially at the beginning of your first year you have to be mean and let them know you mean business and that your class isn't just a blow off course. And second, pencil self-portraits are not a great project by themselves. Apparently, as concluded by all three teachers we spoke with, students find self-portrait intimidating and infuriating as they strive for perfection. Two of the teachers we talked with suggested gesture drawings to begin with and the third teacher has a program she uses to give detailed instruction of how to draw each feature correctly. After listening to these ideas I definitely think both techniques should be combined for the best possible outcome. A few gesture drawings to loosen them up, some strong technical instruction, and then the actual piece that they can create with confidence.
I'm not quite sure I know what I'm doing when it comes to curriculum for the secondary art classroom but I'm running under the idea of "fake it till you make it". Art is trial and error so I think there is a bit of that in teaching it as well. All you can do is jump in with a plan and be ready for that plan to fly out the window any moment and change gears. I can't wait to start this experiment!