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This qualitative phenomenological study examines how women high school principals negotiate work-life barriers and gendered expectations, contributing to unforgetting histories while imagining equitable futures for educational leadership. Semi-structured interviews with ten Illinois women high school principals revealed four themes: constant vigilance in managing gender perceptions, boundary-setting practices challenging organizational norms, relational leadership approaches redistributing power, and work-family integration strategies resisting traditional separations. Using Acker’s Ideal Worker Theory, findings demonstrate how secondary educational leadership remains structured around gendered assumptions of unlimited availability that disadvantage women with caregiving responsibilities. This research recovers gendered histories embedded in educational leadership structures while revealing how participants construct alternative models pointing toward equitable futures. Their strategic responses embody transformation challenging traditional leadership paradigms and power structures.