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This chapter presents the authors’ experiences and reflections as first-generation Chicana scholars who support educational leaders and scholar-practitioners in doctoral programs. They reflect on their own doctoral journeys and share how those learnings inform their practices to improve EdD programs’ impact and the potential benefits to first-generation scholars. They discuss the EdD as a viable path to fulfill the scholarly and professional needs of first-generation and traditionally marginalized people. They then look at ways in which the EdD in Educational Leadership program at UC Davis, which they lead, has structured the curriculum to address the multiple demands placed on such highly sought-after leaders. They end by acknowledging that they are not alone on this journey. Their faculty colleagues and their past and present students continue to challenge them to continue to creatively think about how to improve the program and to continue to advance educational equity and social justice by preparing transformative scholar-practitioners.