This paper explores the work of principals who are leading in low socioeconomic schools in Perth, West Australia, Alberta, Canada, and in Nairobi, Kenya. We developed three cases based upon qualitative data drawn from interviews conducted as part of two doctoral studies in Alberta and Nairobi, as well as a case study from Western Australia. We developed a framework based upon the leadership literature to explore principals’ work, in terms of their priorities and rationales, time intensive tasks, challenges, supports, infrastructure, resources, management of teachers, instructional leadership, parent and community engagement, and resiliency. The framework served as a comparative lens to explore sociological, political, economic, and psychological dimensions of principals’ work-lives. Findings indicated that context was everything. While there were similarities in the school contexts in relation to the impacts of poverty, the nature, severity and how these impacts exhibited varied. There was considerable variation in the political situations which also supported or constrained the work of principals in different ways. Principals were united in their sense of moral purpose which was linked with their resilience but also implied the need to achieve a work-life balance with their extremely heavy workloads. Much of their work involved establishing stronger parent and community relationships, forging partnerships with external agencies and organizations for the purposes of seeking additional funds and establishing special programmes. Principals reported issues with teachers although these varied across macro contexts. Implications related to understanding context, policy and practice, and for leadership theory, specifically conceptualizations of instructional leadership are discussed.