It is rare in studies of long-lived animals to know enough about the personalities and early experiences of individuals to use this information to predict their behaviour during major life transitions in adolescence and adulthood. Here, we examine how personality traits and early experiences predict age of natal emigration and timing of first ascent to alpha status in 169 wild male white-faced capuchins studied at Lomas Barbudal, Costa Rica, 75 of whom emigrated and 23 of whom acquired alpha status. Males were more likely to delay natal emigration if they were more extraverted, more neurotic, if their fathers co-resided longer with them, and if there were fewer alpha male turnovers. More extraverted males attained alpha status sooner.