Early life course conditions and the social origin of families frequently influence the inequalities people experience in adulthood. The transition from education to work is a challenging period during which adolescents make their first employment-related choices and establish the course of their careers. Future expectations guide adolescents' employment-related choices and are assumed to influence future employment outcomes. Therefore, this paper investigates whether family (dis)advantages affect adolescents' employment expectations. We assess various underlying mechanisms that may influence the relationship between social origin and adolescents' employment expectations by using cross-sectional data from the German Socio-Economic Panel (SOEP: 2006-2018), specifically a youth questionnaire administered at age 17. Three key findings emerge. First, family disadvantages, particularly an insecure parental labor market participation, influence the employment expectations of adolescents negatively. Second, supportive parenting does not mediate the relationship between social origin and the employment expectations of adolescents; instead, it functions as an additional positive factor. Third, supportive parenting creates more optimistic employment expectations because it fosters specific "beneficial" personality traits, such as extraversion, conscientiousness, openness, agreeableness, and internal control beliefs.