The article presents the results of a comparative analysis of the life-event structure of generations of Russians based on empirical data from the Russian Social Survey (RSS) wave 9, comparable with ESS. The analysis showed that the life calendar of currently living generations of Russians is quite strongly structured - events occur in certain and rather narrow time intervals and in a certain sequence. A feature of the life calendar in Russia is a high concentration of all the basic events of the first phase of adult life in a narrow time interval, a short period of entry into adulthood. Events of the late stage of life show greater chronological diversity and scenario variability. Significant differences in the life-event matrix of generations in Russia were found, including an increase in the average age of onset of almost all basic life events, an expansion of the boundaries of age-related life stages, an extension of the path of growing up and the transition from maturity to old age, as well as diversification of life scenarios in the professional and family-marital spheres. When comparing the indices of standardisation of the main events between generations, a trend towards destandardisation of life paths was revealed: in older generations, the level of similarity is significantly higher than among younger generations. The main changes occurred in the generation of 1970-1979 and accelerated in the next generation of 1980-1989. Macro-demographic factors, as well as changes in socio-economic and historical conditions, the transition to a post-industrial society might be named among possible reasons. The trend towards destandardisation of life paths in older generations primarily affected people with a higher level of education, while in younger generations it acquired a broader social and class character; gender differences began to appear in the generation of the 1980s. The authors suggest that the increase in destandardisation of life paths may have multidirectional social and individual consequences. On the one hand, new opportunities for development, building a life path taking into account individual characteristics, talents and desires, greater flexibility of life trajectories, a decrease in normativity and social pressure. On the other hand, this may lead to increased uncertainty, social tension, increased inequalities, and a deepening conflict between “fathers and children,” which will increase social risks in the foreseeable future.