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In the contemporary situation of social insecurity and new forms of educational training and work, young people are becoming more inclined to experiment with their educational and employment careers. The processes of extension of the educational period and the validation of new flexible forms of work are results of the global social changes that lead to a more unpredictable and unmanageable situation for people. In this context young people are forced to be more active and to make more individualized life decisions. This paper focuses on two youth groups – high school graduates and university graduates. The analysis aims to outline the specific situation of young Bulgarians: the interlacement between educational attainments, access to the labour market and life values and resourses formed in the family. The quantitative data are drawn from an online survey conducted in 2020 using the respondent method (121 young Bulgarians). The results enable defining the vision of young people with regard to the successful transition from education to employment, and revealing their problems and the specific new lifestyles they are following. Youth’s views are summarized through the prism of their relationships with parents. The study is a good basis for more in-depth qualitative research on young people in transition to employment. [ABSTRACT FROM AUTHOR]