School reform depends on sustained work to strengthen instruction, develop professional capacity, and build organizations that can learn. Yet the political conditions that make this work possible are often unstable. How do reform initiatives establish sufficient legitimacy to support improvement, and how does the design of reforms strengthen or undermine that legitimacy? Drawing on the primary themes explored in The Grit and the Grind: Building High-Performing Education Systems in an Era of Polarization (University of Chicago Press, 2026), this talk examines the reciprocal relationship between politics, legitimacy, and organizational change. The talk explores how the design of educational reforms can earn or erode support among educators and communities, and the consequences for the sustained work of organizational learning and improvement. The central argument is that while legitimacy helps constitute the conditions under which organizational learning and improvement become possible, legitimacy, itself, is tied to the degree to which reform efforts resonate with local identities and collective memory. The talk uses educational reform to explore the broader question of how politics and organizational learning interact, and what it takes to sustain the slow, uncertain work of institutional change.