Using data from 37,570 students in 23 OECD countries in PISA 2006, we examine how national contexts shape the expectation of being a teacher at age 30 among high-achieving students in secondary schools. Our results show considerable between-country differences in the degree of students’ expectation of a teaching job. To address sources of this cross-national variation, we use two-level logit models by linking student-level data with country-level data. Consistent with earlier findings, we find that teachers’ economic status matters for students’ expectation of becoming a teacher. Moreover, our results show that teachers’ social status also matters. Countries’ levels of professionalization of teaching, indicated by whether teachers have a bachelor’s degree and are fully certified, are also related to students’ expectation of the teaching profession. Specifically, in countries with higher levels of professionalization, we see a reduced gender gap in students’ expectation of becoming a teacher.