This chapter expands upon the connected learning model to analyse how digital media fit within the learning ecologies for marginalized youth. It argues that after-school clubs and creative media production can potentially serve as risk intervention strategies for young people on the margins of society. However, the research also reveals that outside of traditional higher education, there remain disconnections between students’ aspirations and economic opportunities. Through an in-depth analysis of four immigrant students, the chapter identifies the key connections that help students learn and leverage their passions and creativity for future success. Students’ learning and goals need to be supported and connected via their peers, academics, adults, their home life, personal interests, and extracurricular activities. Although after-school clubs can fill in gaps in learning, it remains imperative that formal education incorporates students’ creativity and interest-based learning, and contributes to the creation of alternative pathways for economic mobility.