For noncollege-bound youth, swiftly finding a satisfying job upon exiting compulsory schooling might support adjustment. Yet, youths' own job perceptions have rarely been considered in school-to-work transition research. Sequence analysis of monthly occupational status over 4 years (ages 16-20) in a low socioeconomic status Canadian sample overrepresenting academically-vulnerable youth (N = 386; 50% male; 23% visible minority) generated five school-to-work pathways: two work-bound ones with jobs perceived as aligned with career goals ("Career Job," 10%) or not ("Fill-In Job," 26%), alongside three others ("Disconnected" [15%], "Prolonged Secondary Education" [25%], "Postsecondary Education" [24%]). Mental health was strongest in the "Career Job" pathway. Male sex and adolescent employment were precursors to this advantageous pathway, underscoring the crucial role of work experience.