In early childhood education there has long been a focus on “professionalizing the field.” While professionalization initiatives can be well meaning, they can have unintended consequences that exacerbate already existing systemic inequities present in the early childhood workforce, such as restricting opportunities for teachers of color to both progress in their fields and contribute to the knowledge that is often valued in “child-centered” spaces. In this article, the authors explore the consequences of professionalization policies from the perspective of a veteran Head Start teacher, Monae, whose tenure in early childhood started as a child attendee of the Head Start grant that her mother, and several other Black women, implemented in a Midwestern rust-belt city beginning in 1967. Drawing from post-qualitative and narrative methodologies, they foreground Monae's lived experience, as she had a front-row seat to a rising tide of accountability and the ways in which professionalization efforts created structures that limited the participation of many early childhood teachers. The organization that had held the Head Start grant in Monae's community since 1967 failed to meet rising accountability requirements. Monae describes what happened next, when a local district took over the grant. Through these stories, we can learn lessons about how problematic power dynamics and inequitable district policies can weaken the relationships between teachers, families, and Head Start classrooms, as well as between Head Start and the broader community. (author abstract)