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This exploratory qualitative study analyzed two years of anonymous open-ended responses from school and district leaders across Arizona. It highlights the challenges administrators face and provides a foundation for future research to inform policy and practice that better supports school leaders. Despite difficulties, many participants expressed commitment to their roles, citing meaningful work and strong relationships with families and colleagues. Leaders also shared strategies to improve wellbeing and reduce attrition, emphasizing the importance of adequate funding, improved resources, reduced stress, and better work-life balance. Additionally, they advocated for involving educators in policy development to create more responsive and effective systems. The findings offer critical insights into administrator wellbeing and underscore the need for targeted, practical supports statewide.