Individual differences in the transition to adulthood are well established. This study examines the extent to which heterogeneity in pathways to adulthood that have been observed in the broader U.S. population are mirrored in adolescents’ expectations regarding when they will experience key adult role transitions (e.g., marriage). Patterns of change in adolescents’ expectations and the relations between their expectations and subsequent role transitions are also explored. Data from 626 youth in Grade 11 (Mage = 16), Grade 12, and early adulthood (Mage = 23) are analyzed using mover–stayer latent transition analysis. Results indicate 3 profiles of expected timing, corresponding to youth who anticipate early role entry (i.e., early starters), youth who anticipate earlier entry into employment but no other roles (i.e., employment-focused), and youth who anticipate delays in role transitions favoring increased education (i.e., education-focused). Two thirds of youths changed their expectations from Grade 11 to 12. Grade 11 and 12 profile membership predicted role transitions in early adulthood. These findings highlight the importance of adolescents’ expectations and changes in expectations across time in shaping entry into adulthood.