While women have attained higher-level roles and greater representation in higher education administrator roles, the concept of the higher, the fewer (Nidiffer, 2002) represents the "gendered prestige hierarchies" (Allan, 2011, p. 58) that limit women’s representation at more prestigious institutions while bolstering representation at institutions of greater access. In student affairs, women represent a majority of all professionals in the field, though representation in senior student affairs officer roles has not increased significantly since the 1980s (Blackhurst, 2000), with women more likely to advance at institutions with fewer than 1,000 students (Rickard, 1985a). While extensive research exists that illustrates the disparities for women in higher education and academic affairs, little comparable research exists for women in student affairs. This qualitative study sought to understand how women in senior-level student affairs positions have navigated their experiences and career paths in order to advance to their current roles. Using critical and post-structural feminist perspectives of power, the researcher utilized a critical phenomenological approach to consider how nine women in senior-level student affairs positions in large, public institutions understood their career advancement. Participants completed two semi-structured interviews. The resulting themes include an encompassing theme of genderization, as well as four embedded themes: the person on the path, achieving through and with others, conflicting messages of competence and value, and overtasked and alone. Implications of the study require that policy, practice, and research all examine the ways that genderization perpetuates masculine-centered norms and power dynamics that penalize women for deviating from those norms. For current or aspiring student affairs leaders, organizational constructs must be dismantled in order to disrupt internalized genderization by women.