The problem and the aim of the study. The transformation of the educational environment identified the following development priorities for the didactic system: support for lifelong learning; personal orientation and taking into consideration the individual students’ personality structure; use of digital technologies to provide training of the sought-after professionals of the future. The authors propose to implement these requirements with the means and capabilities of modern information technologies that maximally take into account the characteristics of personification. Research methods. Theoretical and methodological analysis and generalization of fundamental scientific works on the research problem, processing of test results, problem solving, student’s choice (digital technology, appropriate software, functionality, sequence of tasks) were applied. The pedagogical experiment was attended by 101 students (35% of girls and 65% of boys) of the Law Institute of Vyatka State University of Kirov, Russia. The Fisher's criterion (angular transformation) was used as a statistical processing method. Results. The essence of the concepts "personal educational trajectory", "personal educational route" has been clarified. The challenges associated with the digital educational environment and a focus on training of the required professionals of the future were taken into account. The problems of personalization of learning (awareness of choice, determination of characteristic factors of the educational model, gradation of the task system) are identified, the content of which is described from the standpoint of the formal scheme of information interaction. An example of designing a personalized educational model is presented by studying the technology of processing spreadsheets (a system of educational problems that guide the trajectory of cognitive performance). At the control stage of the experiment, statistically significant differences were revealed between the experimental and control groups in terms of the level of formation of digital skills and skills that are in demand in the information society (φcrit=1.64<φemp=2.492). Conclusion. Work with digital technologies offers the opportunity to take into account the orientation of the modern educational space towards personalization, the continuity of learning due to the implementation of the described formal scheme of information interaction between a teacher and a student in educational and cognitive activities; designing a differentiated system of tasks; supporting the student's informed choice; social and professional orientation of action.