Utilising an autoethnographic framework, this chapter explores one headteacher’s journey through a decade of headship of schools in challenging circumstances. For those who have never held the role, headship is often understood solely as focusing on curriculum and pedagogical leadership. However, this chapter considers the role in its entirety, focusing more on the limitlessly rewarding yet all-consuming role of being the figurehead of a community. The emphasis will be on key moments that shaped the author as an educational leader from supporting children through the loss of a parent, protecting the perimeter of the building from armed gangs while the school was in lockdown, to celebrating the successes of students and staff and seeking to create a positive culture of respect and gratitude. The chapter will talk through how these moments prompted institutional transformation, but also consider the darker side of headship and the lasting impact that this work had on the author. The author argues that the absolute joy of school leadership comes at a significant cost, the key reason why so few chose to progress to the role and once there why so many do not see out their expected term.