There is a disconnect in higher education between higher education professional practices and valuing the community impact of engaged scholars. In this reflective essay, the authors highlight personal experiences with the process of working toward and earning promotion and tenure in academic settings. Those personal experiences are then contextualized through an examination of the literature regarding evaluation processes, engagement-ready institutions, the history of campus engagement, and the role of community-engaged scholarship in the civic purpose of institutions of higher education. There are clear systemic contradictions that create misalignments between institutional aspirations and individual metrics for success. Faculty serving as boundary spanners advance institutional missions and create transformative student learning opportunities, while sometimes sacrificing personal and professional well-being.