This explorative study validates the relationship between East Orange, New Jersey high school students’ participation in VIP Online Academy’s earn-to learn programs and their perceived positive life trajectory and increased social/cultural capital. This paper also presents realistic data-based and attainable goals for future implementation. This research addresses urban high school students’ self-efficacy and the intertwined nature of their social and cultural capital. Further, this study explores the impact of online leadership programming on high school youth’s social and cultural capital and self-efficacy.