Based on the analysis of the sociological, political, psychological and other research by domestic and foreign authors this paper deals with social processes that determine the choice by the new generations of one or another life pathway version. Rapidly changing social fundamentals and greater ”chaotization“ processes in the post-modern era further specific coming-of-age tendencies. Academic literature deals mostly with following main factors accompanying coming-of-age process of millennials: prolonged youth period, non-linear and varying variants of life trajectories, cycling of events in a young person’s life. It became clear that in terms of social instability, life increasingly affects attitudes and behaviors of young people and requires of them to be flexible in adapting to permanent social transformations, choosing most effective adaptation strategies. Different variants of life, professional and other trajectories of a person in “late modern” era are discussed. New models of success or, vice versa, risks, preventing successful social adaptation developing in Russia and foreign countries are analyzed. Geography of the study presented in this project is not limited to Russia, Europe and the USA, but also includes Latin American, Asian and African countries.