Background: While some recent research has addressed homeless youth from a strengths-based approach, comparative studies of homeless and non-homeless youth from a strengths perspective are few; research that includes youth's views on positive youth development are also limited. Objective: Addressing these gaps and using an inductive approach, adolescents' views on positive development and their strengths were solicited. This study investigated the qualitative differences in views on doing well, strengths and positive development from two youth samples: youth who were homeless and resident youth involved in a 4-H program. Methods: Thirty-eight adolescents participated in focus groups, including five groups from a homeless shelter and five groups from a 4-H program. Content analysis of the narrative responses was conducted. Results: Differences between homeless and 4-H adolescents were found in the areas of happiness, family support, identity, personal strengths, and risk avoidance. Homeless youth revealed adaptation to limiting ecologies (e.g., non-supportive parents) as they sought out other supportive relationships instead and adjusted their views of happiness. Homeless adolescents demonstrated more internal self-awareness compared to 4-H adolescents. Conclusions: By recognizing and capitalizing on the unique perspectives and strengths of adolescents from divergent environments, positive youth development and strengths-based programs and theory can more effectively benefit youth from diverse backgrounds. Understanding youth's views that have normative and non-normative experiences (i.e., non-homeless and homeless) helps further expand the boundaries of developmental models and address how to promote thriving in youth from various contexts.