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The essay briefly outlines the history of community engagement at DePaul University in order to explore how and why universities and colleges are increasingly adopting data collections systems for tracking community engagement. I explore the question of why there is a growing interest in tracking engagement within the academy and suggest that dominant meanings attached to tracking behavior (e.g., recognition, marketing, budget legitimation) overshadow more critical and political rationales for documenting engagement, such as those that emerge out of aspiration to understand how higher education can play a role in promoting social justice and transforming communities. I argue that the latter requires a critical, self-reflexive, ethnographic approach to tracking that illuminates not only positive outcomes of engagement but also the inevitable challenges or failures of engagement that can limit student learning, faculty scholarship, and, perhaps most importantly, community benefit.