In this article, the author shares a story about Chris who publicly transitioned to Courtney during his eighth grade year. Working with a transgender student would require educators as a community to make many decisions for which they had no road map. They need time to educate the community while respecting Chris's need to express himself as Courtney even though he was years away from sex reassignment surgery, should he choose to pursue it (not all transgendered individuals do). To complicate the matter further, Chris, by nature, was anything but patient and, understandably, oftentimes assumed that those in authority should not be trusted. Educators knew that Chris would see their need to take the time necessary to prepare the community as being a rejection of his immediate need to express himself. The author discusses how to prepare a pre-K-8 school community for a transgendering student.