Low-income African American children have been identified among the majority of children without access to high-quality early education (Barnett, Carolan & Johns, 2013). Consequently, they lack the necessary skills to successfully navigate the schooling process (Wesley & Buysse, 2003). This lack of school readiness is only exacerbated by the dissonance between the school and home cultures of these students as it forces them to navigate between the cognitive and behavioral expectations necessary for academic success and the cultural values and beliefs of their families and neighborhoods. For many young children this may be both challenging and overwhelming especially in the absence of intentional transitional support between home culture and school culture, which makes the role of early educators so important. Early educators must be equipped with the necessary skills and knowledge to prepare students to succeed in mainstream culture while simultaneously affirming their home cultures (Ladson-Billings, 1995). In acknowledgement of this need, my dissertation is an auto ethnography in which I highlight my experiences as administrator implementing culturally sustaining pedagogy (CSP) into my predominantly African American early education program. In particular, I examine how I used CSP to foster both student and teacher engagement in an effort to enhance the quality of early care and education that we provided for the children and families. Additionally, I examine how CSP can be merged with the normalized predetermined criteria of quality as defined by developmentally appropriate practices in order to ensure that the cultural and developmental needs of all children are met. This study reflects on the insight I gained about developmentally appropriate practices and the implementation of culturally sustaining pedagogy throughout the journey. Thus, I share my successes, my challenges, dilemmas, and epiphanies. I also provide suggestions for future research.