Although much research has explored the personal, family, school, and social influences on adolescents' career expectations, little is known about the types of family-related career expectations of students and career expectation contexts in school. Using PISA 2018 test data, a multilevel latent profile analysis was conducted with indicators of parents' occupational status and children's career expectations. This research found that family-related career expectations of Estonian secondary school students can be divided into three types: enterprising, resilient, and disengaged. At the organizational level, contexts for career expectations in schools can be classified as enterprising, enterprising and resilient composite, and disengaged and resilient composite types. The research also found that science achievement and gender predicted latent profile memberships at the individual level. It is proposed that to value the science curriculum and its teaching is to invest in future human resources. It is suggested that families and schools should pay attention to stimulating male students' career aspirations. The career expectation types of secondary school students within and between schools are of great significance to the construction of national human resources, the development of schools, and the research of families.