School leadership is an exciting although challenging job. Principals of schools located in rural and remote communities, particular small schools, experience and encounter many challenges that their counterparts in suburban and urban areas do not experience. Concerns over staffing, the quality and availability of materials, facilities, infrastructure and physical access to the school plant are but few of the more readily known challenges. But there are other challenges too such as lack of electricity, workload, feelings of professional isolation, all of which can have an impact of how principals see themselves. This qualitative case study uses a form of grounded theory research to make meaning of the experiences of four small school primary principals in rural Jamaica. The main conclusions are that: principals feel staff and students in their schools are resilient; they enjoy their jobs but feel a sense of professional isolation; and the changing socio-economic policy contexts has led to work intensification.