Quantitative methods were used to investigate attributions of importance to work and family roles and anticipated work–family conflict and facilitation among 353 at-risk Israeli male and female adolescents. Qualitative interviews conducted with 26 of the at-risk youth explored future work and family perceptions. Findings indicated that both sexes anticipated greater facilitation than conflict and demonstrated little exploration and unsophisticated understanding of the work domain. However, perceptions of family were very salient. Females' exploration of family roles was widespread. Both genders understood work as a means to financially support the family. At-risk adolescents' work–family thinking differed meaningfully from descriptions of mainstream youngsters. Implications for career interventions and research with at-risk adolescents are considered.