The key purpose of this paper is to offer an exploration of the career paths of a number of Irish school principals. The information presented is part of a comparative study in the area, involving three island states: Cyprus, Malta and Ireland. The study provides an insight into how individuals become principals and how they perceive themselves in the role. The information is sourced through personal narrative. Qualitative in-depth interviewing is employed as the primary method of data gathering. Participants are posed a range of open-ended questions about their personal lives and about their initiation into their professional responsibilities. The results show that participants offer a variety of reasons for becoming teachers initially and a variety of reasons for seeking and achieving promotion to the post of school principal after a time. Family members and family experiences have an important function in influencing the lives of prospective leaders. With no formal training to prepare newly appointed principals for their roles, most report significant difficulties initially, particularly with managerial tasks and bureaucracy. In spite of these difficulties nonetheless, all participating principals report that they enjoy their roles. The results of the study demonstrate that the Irish principals interviewed in this research, experience similar challenges and rewards to those interviewed in earlier and concurrent studies internationally.