This paper extends discussion of parental influence on adolescent’s occupational intentions by including parents’ socioeconomic status and by arguing that entrepreneurial self-efficacy (ESE) as instrumental to both entrepreneurial intention and employment intention. The adolescents’ social milieu is proxied by their parents’ occupational type and formal education and income levels, which adds their social and business networks, schoolteachers and fellow students to the adolescents’ process of forming either entrepreneurial or employment intention. We ask whether adolescents’ occupational intentions depend on the interaction of their social context and specific personal cognitions (namely ESE, psychological capital, hubris, academic performance, and gender). Using fsQCA and 203 adolescent-parent dyads, we find that employed parents, rather than entrepreneur parents, are more consistently associated with adolescents’ entrepreneurial intention. The cognitive conditions interact synergistically and substitutively as core conditions to influence entrepreneurial intention (or inversely employment intention). Low self-assessment of academic performance is a core condition for high entrepreneurial intention, and both sexes select their occupational type according to bespoke configurations of their causal conditions, with implications for educational policy, and further research.