- Positive youth development posits that all youth possess the capacity to change and grow as they interact with their contexts. That capacity is activated and nurtured by a beneficial ecological environment often unavailable for homeless youth. Only a limited number of studies focus on the positive development and strengths of homeless teens or what positive development means to youth in general. Theories and conceptualizations about adolescent development are most often constructed by adults without reflection from adolescents themselves. Therefore, using a youth-centered inductive approach, adolescents’ opinions and views on positive youth development, well-being, strengths, and success were sought through ten focus groups with 18 homeless youth and 20 non-homeless (4-H) youth, ages 12 - 17. This dissertation is comprised of two manuscripts that use qualitative content analysis to report on the contrasting views of homeless and 4-H youth and youth’s collective perspectives on the study topics as well as responses to a predominant model of positive youth development. Manuscript one addresses the discrepancies in youth’s views and experiences by subgroup - homeless or 4-H. Analyses revealed youth’s different conceptualizations of their sense of self, personal strengths, happiness, family support, and risk avoidance. Homeless youth demonstrated deeper self-awareness in describing the strengths of their personal qualities, as opposed to 4-H youth, who cited their strengths in terms of activity related accomplishments. Findings also demonstrated homeless youth’s adaptation to their lacking ecologies, such as non-supportive parents, as they sought out other health-promoting relationships in their place. Homeless youth also viewed risk avoidance as an aspect of doing well, unlike 4-H youth. Manuscript two highlights youth’s collective perspectives of doing well. According to this analysis youth’s views were focused on the future and reaching their goals, including enjoyable careers and educational achievements. The youth also valued social skills, especially humor and humility in relating to people, to be successful. Unexpectedly, youth held different interpretations of what is traditionally understood as character and how character is conceptualized by the positive youth development framework. The findings of the two studies, considered concurrently, augment recent understandings of positive youth development and youth well-being by including diverse adolescents’ perspectives which may lead to more relevant programming for youth. By recognizing the unique perspectives of youth from divergent environments, programming, theory, and policy involving positive development and strengths-based approaches can more effectively represent the strengths and views of youth from diverse backgrounds.