Data from past economic downturns show that "recession graduates"--those graduating from high school or college during a recession--may have worse outcomes in earnings and health for years or even decades to come. MDRC sought to work with stakeholders to better understand the challenges recent graduates are facing in the current context and to plan initiatives to help them succeed. MDRC was able to set up an initiative with partners in Bridgeport. This brief highlights the following lessons from the implementation of the initiative in Bridgeport that may be useful for other communities that are interested in launching similar initiatives: (1) Building Partnerships Requires Identifying Win-Win Opportunities; (2) Recruiting Young People Requires Persistence and the Use of a Variety of Strategies; (3) The Choice of the Message and the Messenger Affects Recruitment Success; (4) Developing Relationships Between Staff Members and Participants Is a Prerequisite for Career Planning; and (5) Support from Staff Should Persist After Participants Are Referred to and Enroll in College or a Program, or Take a Job.