This paper examines the choice of the teaching profession in contemporary Japan based on the theory of anticipatory socialization. The study relies on Bourdieu's habitus theory to examine the choice of the teaching profession from a social background perspective, because the rational career choice model, which focuses on working conditions and environment, cannot adequately explain this choice. The results suggest that the opportunity to enter the teaching profession is embedded in school experience, in particular the "apprenticeship of observation," which influences the strength of the desire to become a teacher and the attrition rate in training programs. Finally, given the contemporary educational issue of the decline in the number of aspiring teachers, this paper discusses the relationship between the study results, educational policy, and teacher culture.