This article explores the sense-making experiences of one specific stakeholder group in education reform -- school leaders -- who find themselves wedged by significant material challenges, on the one hand, and disparate reform efforts, on the other hand. The research draws upon experiences from the Philippines where reform efforts are significantly complicated by both poverty and disasters, as well as a sense of a 'culture of crisis' more broadly that has subsequently developed. Using the narrative experiences of two school leaders, this inquiry explores the issues and challenges school leaders encounter as they engage in what are described as 'custodian' and 'crisis' leadership practices, as they navigate an educational system typified by a dearth of resources, physical disasters, and a persistent discourse of impending disaster. The research reveals a need for a more circumspect approach to educational reform, particularly distributed leadership, that actually takes significant, material contextual factors seriously, and that is responsive to broader discourses of disaster more generally.