This paper explores some of the reasons that primary head teachers in urban schools give for staying in a highly complex and demanding professional occupation. The paper is divided into two sections. The first section contains an overview of what is involved in primary headship in the English setting and what is distinctive in the urban setting and its impact on headship. The second section of the paper draws on a small exploratory study to consider some of the key factors that influence urban primary school head teachers to stay in their posts. The paper details the emotional complexities and costs involved in this work, focusing on resilience, commitment, and the rewards of doing what is seen as a worthwhile job, which all contribute towards retention in a challenging profession.