Personality traits have frequently been observed to be associated with subjective well-being. It has been suggested that personality traits may lead individuals to experience life in certain ways which, in turn, influences their subjective well-being. However, the exact mechanisms underlying this relationship remain unknown. The present study hypothesized that the ways in which individuals endorse strategies for achieving happiness (i.e., orientations to happiness: through a life of pleasure, through a life of engagement, or through a life of meaning) mediates the associations that personality traits have with subjective well-being (i.e., satisfaction with life, positive affect, and negative affect). Our results indicated that an orientation to meaning in life partially mediated the relationship between extraversion and life satisfaction. In addition, all three orientations to happiness (i.e., pleasure, engagement, and meaning) partially mediated the relationship between extraversion and positive affect. Discussion focuses on the implications of these results for understanding the connection between personality traits and subjective well-being.