This Scholarly Personal Narrative (SPN) builds on McCluskey-Titus and Cawthon's (2004) use of the "grass is always greener on the other side of the fence" metaphor to explore the experiences of a Black American woman faculty member transitioning from her role as a student affairs administrator to a full-time, tenure-earning faculty member. Specifically, I recount how my positionality as a Black feminist scholar-pracademic was essential in successfully navigating the administrator-to-academic transition from one predominantly white institution (PWI) to another. Derived from a deductive thematic analysis grounded in Collins' (2000) Black feminist epistemology and relying on metaphors related to greener grass, I present several narratives that illuminate my experiences transitioning from administrator to academic and offer strategies that may be useful to Black women considering or in the midst similar transitions.