As the "people's college," community colleges have a reputation of being more welcoming of women--as students, faculty, and administrators (Townsend & Twombly, 2006). However, the current percentage of women leading community colleges, which is hovering at 29% (American Council on Education, 2007), begs the question of why parity is not witnessed at the helm of these colleges, especially when 57% of community college students are women (NCES, 2004). The present phenomenological study investigates the positions six women presidents hold, critical incidents that have impacted their career decisions, the role of mentoring, and how these leaders are encouraging others that will eventually take their places. Key emergent themes include the role of serendipity, encouragement by others to test the leadership waters, self-determination to pursue a presidency, and career sequencing based on family.