These reflections on school and schooling come from the crucible of practice in the real world of K-12 education. Written by a school leader for his school, these essays have a timeless and universal appeal for parents, grandparents, educators, school leaders, and all who care about the formation of the next generation. Chip Denton, founding head of Trinity School in Durham, North Carolina, applies multiple lenses—theological, pedagogical, and practical—to reflect on the ways a school's mission drives a multitude of mindsets, traditions, and habits in a community of learners. Schools are places where words matter, and in this volume you can see a school leader working to match word and deed in the life of a school. Collected from Denton's regular Head Lines letters to the Trinity School community over the last decade (2015-2024), these reflections engage the complexities and tensions of excellence in education. The letters can be read individually, but together they tell how one school's story illustrates Nietzsche's saying that one who has a why can manage with any how.