The article is devoted to the analysis of differences in educational and career trajectories of representatives of different generations. The generational division is based on the theory of N. Howe and W. Strauss, V.V. Radaev. The educational and career trajectory is understood as a sequence of motivated life choices of an individual within the framework of educational and professional institutions that affect the social and labor status of an individual, mediated by the use of their capabilities and abilities. The article analyzes the discourses of modern sociology, which are reflected in the state of the current labor market due to the high rates of technologization and automation. The approaches of J. Rifkin, A. Touren and O. Toffler are analyzed. Thus, the labor market is becoming more dynamic and flexible, and the opportunities for professional growth and self-realization are expanding. This actualizes the study of new strategies for accumulating professional capital of a personality, the motives of educational choices of the younger generation and their attitude to a career. Based on the author's research by the method of in-depth semi-formalized biographical interview, the factors of educational and career trajectories of representatives of three age groups have been identified: born before 2003 (generation Z), born in 1989-1998 (generation Y), born in 1969-1979 (generation X). It has been revealed that the younger generation is prone to frequent employer changes, combining several activities at the same time, choosing educational courses and internships in order to accumulate professional skills and a low career planning horizon. While the older generation is focused on more stable forms of career trajectory, the choice of higher education as the dominant one. The factors common to all the studied generations that influence the change in the vector of the educational and career trajectory include: the propensity of a student at school to study subjects of interest, parental family support, satisfaction with the education received, the establishment of weak connections in the learning process, the presence of goals and motives for professional activity, financial status, gender. The practical significance of the work lies in the possibility of using the data obtained in the field of educational program design, HR, consulting, and career counseling.