While academics increasingly point to the value of engaged scholarship, we describe a more extreme form which we label as "deep partnering"—a long-term, holistic, and dynamic collaboration between academics and practitioners to achieve shared goals. Deep partnering involves interdependent and evolving interactions between academics and practitioners over an extended time period. While such relationships enable generative impact on important issues, these relationships remain challenging as academics spend time in the practitioners' complex worlds, surfacing paradoxes due to the partners' conflicting roles, time horizons, and goals, as well as uncertainty in the partnership's evolution. In this essay, we reflect on our experiences working closely with practitioners on a program of research over more than a decade in order to expand on a deep partnering approach, including the paradoxes and emotional discomfort it surfaces, and we identify practices to navigate these paradoxes.