Given the current tumultuous education climate, we as EdD faculty seek to engage in critical reflection and reimagine the affordances--opportunities for action (Gee, 2008; Gibson, 2014)--provided by our program structures and our teaching practices. In this article, three faculty members (including one department chair and one interim program director) among the many who actively engaged in reimagining an established online EdD program to be launched Fall 2023 discuss their critical self-reflection experiences. Specifically, we discuss how our backgrounds and/or the current socio-historical climate influences our thinking as we, along with our colleagues, have grappled with redesigning an applied EdD program.