Slow and incremental improvements are no longer enough to help school districts meet the challenges they face. Instead, districts must enact bold, innovative, and durable systemwide shifts. This brief details how to both encourage these shifts and learn from districts' attempts to implement them, the Center on Reinventing Public Education (CRPE) funded and studied pilot programs in 11 districts during the 2023-24 school year. Each of these districts had a "Bold Idea"--defined as an innovative initiative designed to "make student learning more joyful, individualized, and relevant"--and met conditions for "readiness" to address the barriers inherent to creating durable change. Over the course of the study, seven key challenges came up again and again--along with lessons learned from meeting those challenges head on. To succeed, pilots needed committed, executive-level champions, as well as succession plans for what would happen if those champions left the districts. Pilot teams needed change-management strategies, relationship-management strategies, and political savvy to secure support from key constituents, like teachers and policymakers. Collecting user feedback data also allowed pilot teams to stay nimble and adjust course when necessary. Findings show that despite the fact that these 11 districts had been identified as the most ready to create systemic change, being ready did not prevent them from experiencing challenges--what set them apart was their ability to navigate these challenges by using specific change management strategies to address specific problems.