Why have efforts to rebuild an Island ravaged by financial uncertainty, natural disasters, political and social unrest, and epidemics gone awry? It's due in great part to the fact that the main pillars of our democratic government, the Executive and Legislative branches, have not understood, much less exploited, the potential that exists in the digital age to effect a transformation of the country. Rebuilding an avant-garde society requires a government capable of making the transition from the physical models of the past to the digital models of the present. Digital transformation in governments is possible if we dare to make revolutionary changes across all branches at every level. Any central plan must leverage and empower the role of civic tech leaders and their practical knowledge to respond and contribute to these efforts. This book presents a roadmap with a clear strategy to make a leap from proposing great ideas to achieving visible execution. Over a dozen plans that have been developed over the past 12 years on economic development, infrastructure, security, and fiscal sustainability are reviewed and analyzed. Its purpose is to establish the criteria to be followed for a radical execution of the digital transformation of Puerto Rico, and may be applied to any jurisdiction.