This study explored the experiences of low-income students of color who participated in a work-based learning (WBL) program while attending a Catholic high school. Historically, research on student outcomes in WBL programs has been mixed, and few studies have provided insights into how low-income youth of color can benefit. This study utilized a phenomenological methodology to capture hope among these youth and to delineate these students' lived experiences within their relational, organizational, and sociocultural contexts. The results showed participants' goal setting and motivation were fostered by a sense of connection to others at school and a collective belief that success was possible for all students despite whatever challenges they faced. The participants also discussed hopes for the future within the context of workplace support, religious faith, and past hopelessness. The results provide avenues to design WBL programs that consider students' supports and barriers and further contextualize hope theory.