This study uses critical race theory and qualitative interviews to understand the perspectives of 10 Black males that have entered the field of education through non-traditional routes. It seeks to highlight the rationale for not choosing education as a first option, what eventually led them into the field, and finally how educational leaders might better recruit. As the field continues to evolve with demographics still heavily favoring women, decision makers in school districts, universities, and alternative certification programs need to understand the best methods to recruit and retain Black males in education. The findings of this research will benefit these stakeholders and their constituents and inform practitioners, particularly after the COVID-19 pandemic and current teacher shortage.