This paper presents the annual report of Philadelphia Youth Network (PYN) for 2009-2010. This annual report documents the journeys of several participants in their programs who have gone on successfully to college and careers, and demonstrates the potential of young Philadelphians to begin to reach their goals. In telling these stories, they build on PYN's 2008 annual report, "On the Map," which visually displayed the increasing breadth and depth of workforce preparation activities available to young people all across the City. This report also highlights the milestones achieved by PYN in 2009 and 2010. [For the 2008 Annual Report, see ED540216.]