Utilizing both perspectives from modern positive psychology and common, conventional theories, this article examines how graduates of high schools and colleges choose individual educational routes (IER). The significance of the issue of choosing IERs is discussed; additionally, the current state of research in this area is described. Methodological difficulties were revealed in the study of the choice of IERs by graduates of high schools and colleges and in the practice of psychological and pedagogical support for choice. Major contradictions and unresolved problems were identified in the theory and practice of psychological and pedagogical support for graduates of high schools and colleges in choosing their IERs. The most important data and findings on the choice of IERs made by modern high school and college students are presented, contradictions in the available data are revealed, and the specific features in disabled students’ choosing IERs are described. In addition, an analysis of the main approaches to studies of students’ choice of IERs (sociological, subjective and based on positive psychology) was conducted. Furthermore, the importance of positive psychology for solving existing problems in research and in the practice of psychological and pedagogical support for graduates of high schools and colleges in choosing IERs was described. The article provides a brief overview of recent positive psychology research on the choice of educational routes, and outlines the prospects for its application in solving urgent research and practical problems related to psychological and pedagogical support for students’ choice of IERs.