The present study is the first reported analysis of participant data from an afterschool leadership development program targeting the elementary to middle school transition for fifth-grade students. Data were collected from 2012 to 2015 from 261 adolescents who self-selected to participate in the afterschool program and provided parental consent/assent; 60% of the sample were female, 24% lived in rural areas, and 33% attended schools in low socioeconomic status (SES) areas. Participants completed the Developmental Assets Profile (Search Institute, 2005) and a demographic questionnaire. Outcomes of interest for the analysis included relationships between sample characteristics (SES; rural vs. nonrural), support and empowerment (external assets), and positive values and commitment to learning (internal assets) Cluster analyses identified 3 distinct groups of high-, average-, and low-asset students. ANOVA found that contrary to what was hypothesized, it is not only high-asset students who self-select to participate in a leadership development program. Moreover, students from high SES schools and urban areas were just as likely to be represented in low-asset subgroups as students from low SES and rural schools.