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This qualitative study examined systematic career hesitation among women in educational leadership, identifying a recurring pattern that begins when they are classroom teachers and persists through each transition to the superintendency. Drawing on Bourdieu’s Habitus Theory and Feminist Theory, the study analyzed interviews with current female superintendents and search consultants, superintendent leadership profiles, and community surveys. Findings reveal two interrelated forms of hesitation: systemic, embedded in the social constructs and institutional norms of educational leadership, and systematic, recurring across career stages—often without conscious awareness. This “hesitation cycle” shapes aspirations, self-perceptions, and advancement decisions, requiring external validation and mentor intervention at every level. The study reveals how gendered social conditioning perpetuates underrepresentation and offers implications for targeted, sustained leadership development.