Building upon the concept “problem-free isn’t fully prepared,” this chapter explores its corollary: “fully prepared does not mean problem-free.” The discussion advocates for a both–and approach to youth development, recognizing that young people can build both assets and resilience while facing challenges. Outlining the unique position of community youth development programs to provide flexible, customized support for youth thriving, the discussion emphasizes the importance of communicating the value of these programs to parents, teachers, and the broader community. The chapter summarizes significant research that has shaped positive youth development practice, including the National Research Council’s seminal 2002 report, Search Institute’s 40 Developmental Assets, Youth Development Strategies Inc.’s Community Action Framework for Youth Development, and University of Chicago Consortium on School Research’s Foundations for Young Adult Success. These frameworks consistently emphasize the importance of supportive relationships, challenging activities, and meaningful involvement across various contexts in young people’s lives. Each framework is accompanied by tips for practical application, including: (a) intentionality in program design, (b) recognizing the diverse strengths young people may possess across different contexts, (c) unique roles that different settings play in developing skills and competencies, and (d) the importance of creating opportunities for both action and reflection.