In January 2017, at various Women's Marches spanning the world, women with decades of activism under their belts held signs that called attention to their incredulity at having to resist government policies that threatened control over their bodies. This paper explores a similar persistence of stereotyping and discrimination that women in positions of educational leadership have faced for decades. Herein, we describe and explore the professional involvements and perspectives of fourteen women possessing diverse positionalities holding various positions of leadership in education, and we examine overt and covert forms of discrimination that affect decision-making and authority. Moving beyond evidence of stereotyping, pigeon-holing, and discrimination, this paper takes up Karen Barad's theory of intra-action to understand these positionalities and subjectivities in a different light. In so doing, we explore the ways our participants adopted postures of resistance as they accepted, rejected, and wrestled with discrimination and stereotyping while negotiating positions of leadership.