Introducing students to self portraits can be a complex task. A review of shape, form and value is required to set a foundation for the basic structure of the face. In addition, students are prompted to begin their studies from observation where they learn to break down form from reality and interpret what they see into their drawing. The process of observation requires careful attention from the teacher as it can often unearth insecurities around identity and physical appearance. Ensuring that the process is grounded in affirmation and attention to student identity and diversity is critical to developing each students’ artistic lens.