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Little is known concerning how and why women transition from faculty into academic leadership within the community college environment. When examining the lived experiences of women, the analysis of gender from a woman’s perspective remains problematic in any traditional phenomenological sense. Therefore, this study utilized a ‘post-phenomenological’ rendition of gender to strive for deeper understanding while remaining true to the pursuit of phenomenology and at the same time recognizing the influence of gender on the experiences and perceptions of the participants. Nine female deans from southeastern community colleges participated in this post-phenomenological investigation. Four essential structures emerged from the data to represent their transition from faculty into academic leadership offering significant insight into the how and why of their transitions.