This report from the Center on Reinventing Public Education at Arizona State University examines efforts by 11 school districts to launch “Bold Ideas”—innovative initiatives designed to make learning more joyful, individualized, and relevant. Selected for their readiness to pursue systemic change, districts piloted these initiatives during the 2023–24 school year while navigating the challenges of early implementation. The study identifies seven recurring obstacles, including leadership turnover, political resistance, and the need for effective change-management strategies. Findings underscore the importance of committed executive-level champions, strong succession planning, coalition-building with teachers and policymakers, and mechanisms for gathering user feedback to adapt in real time. While readiness did not shield districts from difficulties, their ability to strategically respond distinguished their progress. The report offers early lessons for districts, funders, and policymakers interested in scaling durable transformation, highlighting both the promise and the complexity of creating systemwide change.