Combining work while attending college is a common strategy for youth with limited financial means to pursue postsecondary education. However, we know relatively little about the socioeconomic contexts behind the different work and school decisions and whether the meaning of each work and school experience vary by different socioeconomic backgrounds. Following a national sample of young adults, this study explored how personal financial responsibilities and parental social support are associated with employment or enrollment in college and youths' perceived relevance of them for their prospective careers. Youths' personal financial responsibilities were associated with higher odds of working only and combining school and work, compared to attending college only. Youths' personal financial responsibilities were positively linked to the career relevance of their work and school experiences, but only when they were experiencing low parental social support.