For non-college-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 four years (ages 16 to 20) in a low-SES 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.