This article examines Black educators' experiences in Grow Your Own programs along a teacher development continuum at the intersection of social and human development constructs and frameworks, such as double binds and Phenomenological Variant Ecological Systems Theory (PVEST). More robust and nuanced interpretations of how Black educators grow and sustain their presence in the field of education are explored utilizing these analytical tools to determine how Black educators make their way along the teacher development continuum. Findings related to Black educators' development as they transition as students to teachers, using double bind constructs at each stage of PVEST, are described, and research and praxis questions are extended for implications.