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Aligned with AERA’s 2026 theme Unforgetting Histories and Imagining Futures, this qualitative case study explores how principals support teacher workplace well-being in high-poverty, majority-minority elementary schools. Conducted in three Title I schools in Palm Beach County, Florida, the study is grounded in Seligman’s PERMA Theory and investigates how leadership practices align with the five elements of flourishing. Data sources include a PERMA-aligned survey, interviews, focus groups, and document analysis with three principals and 18–30 teachers. School sites were selected based on district climate data and principal tenure. The study addresses four research questions focused on leadership, teacher perceptions, and cross-site comparisons, contributing insights into how centering teacher well-being can advance educational equity and reimagine the future of school leadership.