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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 at University of Missouri for over 40 years, 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 own 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? Why do you paint yourself all the time, are you that self-absorbed? (Maybe!) 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 it provides--the freedom to make mistakes. 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. 
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