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This qualitative pilot study explores how district leaders describe and experience occupational wellbeing amid rising demands, political pressure, and post-pandemic challenges. Drawing on focus groups with superintendents and cabinet-level officers, findings reveal that leaders view stress as inherent to the role, yet describe wellbeing as closely tied to district culture, crisis management, and the wellbeing of others. Insights inform the development of a future wellbeing survey and suggest that leader wellbeing may be critical to retention and organizational effectiveness.