The relevance of the study is determined by the special significance of the process of creating conditions for high school students to make multiple choices, since modern young people cannot imagine their existence without constant situations of bifurcation. The main goal set by the authors is to develop an algorithm necessary for understanding the logic of self-determination of a high school student in culture, which can also be used as a basis for the practical activities of a teacher. Based on this algorithm (working scheme), the teacher can offer specific options for situations of choice for high school students. The article provides examples of such situations, tested in literature classes. It is shown that the process of choosing opportunities for realization of personal potential by high school students can be more effective if the teacher is able to create pedagogical conditions for such actions as individual refraction of the norms and values of society, identification and justification of the value-semantic foundations of life activity; choice of goals and means of self-realization based on personal potential, choice of ways and forms of life, responsible design and implementation of individual trajectories of personal/professional formation and development. One of the important conclusions of the article is the one that the leading way of self-determination of a student in culture is a play activity (real or imaginary), age-appropriate and fixed in the mind as a cultural norm. This justifies the need to use such a method of pedagogical support as adaption for the stage (from expressive reading of a literary text to a school theater performance). It is shown that a high school student’s living through events by the medium of a literary work is often a preventive measure in relation to possible undesirable situations in the future, contributes to the self-determination of a person in culture, which is relatively permanent and proceeds throughout almost a person’s entire life.