The author has been an art educator at the largest urban high school in Toronto, Canada, for the past six years, and every year he attends his students' convocation. Traditionally convocation is held at the beginning of November, and those Grade 12 students who graduated the previous spring return to high school for a celebration and to receive their diplomas. For the last few years he has been fortunate to teach in an art program that allows him to instruct a core group of students from Grades 9 to 12. He values the unique opportunity to grow with his students over a four-year span: it not only allows him to model a passion for the arts and to share his knowledge, but also allows for the creation of a communal environment that has the possibility to transcend time and distance. In this article, the author provides a narrative history of his development as an art educator, reflecting on the aims and outcomes of his practice, filtered through the events and people who have shaped and inspired him to become the educator he is today. His narrative unfolds as if it has its own life, linking up and overlapping with the stories of other artists and educators in multiple layers. The small vignettes he relates here will show how he came to art education and how, through a process of reflection, he has grown as an art educator.