Despite the egalitarian ideal of “college-for-all,” research shows that working-class young people remain disadvantaged in the transition to college and work. However, while some experience upward mobility, most go to work. Yet, scholars have paid scant attention to these variant pathways to adulthood within the working-class young individuals. Particularly, they have not fully recognized varying roles that teachers play in the transition of working-class students to college and work. Moreover, working-class young people’s understanding of the transition to adulthood has been discussed only insufficiently in the literature. Therefore, this dissertation, consist of three independent but complementary essays, investigates various transitional experiences of the working-class young people. The results draw on a one-year of ethnography in a South Korean high school as well as the broader community which serves young individuals from working-class homes. The first article of the dissertation shows how teachers, as “mobility sponsors,” selectively help working-class students to go to college. Whereas teachers provide sponsorship for the college admissions of those working-class students with academic excellence, they take a “laissez-faire” approach for ordinary working-class students without helping them directly. The second article illustrates how teachers stigmatize working-class students who seek to become working-class workers. Teachers stereotype working-class work and criticize vocational aspirations. I also find that work-bound students report that teachers’ negative comments create emotional distress for them. The third article explores young workers’ subjective understanding of their status in the college-for-all society focusing particularly on gender differences. The study finds that female workers are pessimistic about their status because they believe that their lack of college education might adversely affect their transition to adult roles. On the other hand, male workers are optimistic as they believe that their future compulsory military service will help them to become a respectable male adult. Overall, the dissertation discusses the social implications of the college-for-all society by showing various struggles of working-class young people. It also calls for policy efforts to provide institutional support for their diverging pathways to adulthood.