When teachers pursue an artistic career parallel to teaching, a potential for conflict arises between the subjects they explore creatively and public expectations regarding the teacher's role as a model of morality. This paper offers a critical analysis of these expectations as articulated in the landmark legal case "Shewan." The paper argues for a better balance between teachers' right to free expression and the need to uphold public trust in teachers and teaching and urges art teachers' associations to play an active role defining the special standard that teachers can be reasonably held to in their private off-duty artistic pursuits.