One of the most coveted benefits of teaching in an independent school is that, in many schools, the educator's child can attend tuition-free or at a significant discount. But as any educator who has taken advantage of this benefit knows, having dual roles in a school--that of school administrator or teacher and parent of a student attending the school--has its challenges, too. In this article, the authors discuss the challenges and provide some suggestions for school administrators, teachers, and teachers with children in the school.