Educational attainment defines workforce success, and a robust workforce drives economic stability and growth. Therefore, everyone has a stake in developing systems that promote strong education outcomes and successful transitions to the labor market: businesses and employers that aim to simultaneously build up the next generation of consumers and strengthen the future workforce; elected officials who wish to sustain the city's current prosperity and growth; parents and concerned community members who want a vibrant, healthy community; and youth themselves, who by and large want to lead stable, productive lives. Momentum has been building -- now is the time for the District of Columbia to develop such a system. Recent studies suggest thousands of youth between the ages of 16 -- 24 are disconnected, which is commonly understood to mean young people who are neither in school nor working. High dropout and unemployment rates and low post-secondary education attainment rates among District youth have led to a series of thoughtful and focused examinations of how the District of Columbia can reconnect youth to opportunity. Raise DC, the District's public/private partnership dedicated to establishing cradle to career alignment, is leading the charge with its focus on youth reconnection. This -- combined with the engagement of the foundation sector on the needs of disconnected youth and the recognition of other government and community working groups on this emerging and high-need sector of the youth population -- has opened the window of opportunity to combat youth disconnection through cohesive, evidence-driven, and cross-sector systems change.