Guided by Standpoint Theory, researchers conducted this case study to identify factors influencing access to Oklahoma's secondary school principalship for four female first-time principals. Regardless of equity legislation and increasing numbers of females with advanced degrees, the numbers of men and women who hold secondary school administration positions continue to be disproportionate to their numbers in the teaching profession. Three standpoints emerged: In the transition from teacher to administrator, each participant was nurtured by another individual; male sponsors were their primary encouragers; and participants had strong emotional investments in the schools and communities of their employment. Aspiring female principals should cultivate strong support systems, seek out mentors, and strengthen their professional networks. Accepting stepping-stone administrative positions may be an essential starting point for aspiring female secondary principals; administrative skills can be gained through internships, assistant principal positions, and administrative positions in lower grade levels.