The action-project method was used to explore similarities and differences in the goals and activities of mothers and sons, and mothers and daughters, working together to facilitate a successful future transition to adulthood. Participants were 10 mother-daughter dyads and 8 mother-son dyads, with a range of ethnicities and income levels. Data included video-recordings of conversations, transcripts of interviews, and self-report logs of activities. A team-based, constructivist analysis, grounded in the principles of action theory, yielded a complex pattern of results revealing the importance of attending to gender in the transition process. The dyads generally pursued similar types of transition projects (e.g., becoming more independent) and encountered similar kinds of barriers (e.g., lack of time). However, mother-daughter dyads were more active in pursuing their projects, engaged in more mutually open conversations, and experienced less conflict than their mother-son counterparts. The findings are discussed in terms of dyads' conceptualization of adulthood and implications for gendered patterns of education and career choice.