What if, in 2020, a new generation of leaders ends the war in Iraq and turns its attention to pressing domestic issues eventually resulting in a healthier economy and renewed investments in the urban core? What if, in 2020, having tried and failed at the beginning of the 21st century to improve urban education with prescriptive, high stakes accountablity measures, policymakers turn to alternative solutions once considered anathema within the public arena? What if, in 2020, the widespread availability of free Wi-Fi and other innovative technologies reinforced by federal and state policies encourage grassroots solutions fueling local ingenuity and productivity? What if, in 2020, states' inability to provide sustainable funding for urban districts combines with the global economic crisis, environmental disasters, and a prolonged war in the Middle East to dramatically diminish available school resources? A group of stakeholders from eight Ohio urban districts tackled these questions. This brief explains the context and process for this work and discusses the implications for state-level policymakers interested in supporting such a transformation of urban education as envisioned by this group in Ohio. Suggested are possible approaches policymakers could take to implement these recommendations and prepare not only to survive but to thrive in the challenging and uncertain times ahead. (Contains 33 endnotes.)