In 2008, my friend and sometimes mentor Frank Stack visited my studio and suggested that I paint 100 self-portraits. This may be a suggestion he's made to lots of people--in addition to being a master artist who has painted his own face many times, he taught painting for over 40 years at University of Missouri, and knows all about the well-placed suggestion. For me, it took 11 years to make use of Frank's prompt (I was always late with my homework), but now that it's underway, I have found many unexpected layers of meaning, and artistic rewards aplenty. On a purely practical level, I can see why Frank recommends this to developing artists: I remain, after all, my most ready, cooperative, and cheapest model. I almost always follow my instructions for poses, and I can take hundreds of photos to get where I want to go without trying anyone's patience other than my own. It can be scary to put self-portraits out into the world. I can hear in my own head, and sometimes from actual other humans, the criticisms: This doesn't really look like you. Why don't you SMILE? You look much younger in your paintings. I've learned, mostly, to set aside the fear of such comments. One of the many rewards of this assignment is the sense of freedom that accompanies it, which really makes room for artistic growth: you know if you get this self-portrait wrong, you have 67 more tries. This knowledge provides both comfort and bravery. Frank knew what he was doing.