The present study takes a motivational perspective that views youths’ educational and career engagement as influential and potentially competing for the same motivational resources in the transition to adulthood. We investigated whether motivational engagement with educational and career goals in the year after high-school graduation was differentially associated with educational, career-related and subjective well-being outcomes 2 and 4 years after school graduation. Our longitudinal study of a multi-ethnic sample of Los Angeles high-school graduates followed participants 2 years (N = 561; 61.5 % female) and 4 years (N = 364; 59.8 % female) after high school graduation. The findings indicate that motivational engagement with educational goals after high school graduation predicted educational attainments and psychological well-being at follow-up 2 and 4 years after graduation, and occupational progress at 4 years after graduation. Work hours assessed shortly after high school graduation were associated with poorer educational outcomes both at 2 and 4 years after high school. Occupational goal engagement was not associated with better outcomes, but predicted less educational attainment 4 years after graduating. Thus, educational goal engagement predicted favorable outcomes, whereas career-related goal engagement for the most part was neutral with some select associations with negative educational outcomes. A strong motivational commitment to educational goals, but not to career goals, is an important component of a successful transition to adulthood.