Digitalization of society, including the labour market, noticeably changes women's and men's career expectations and career strategies.  Gender philosophy, questions about gender identity, and gender inequality are questions, the answers to which are critical: “the changes in the social status of women and men in our time have fundamentally changed many familiar stereotypes” (Mikhailova, 2011). Kontakt InterSearch Russia conducted a series of studies for Forb’s magazine (Kontakt InterSearch Russia, 2021a, b, c; Forbs, 2021) that evaluated the career expectations of respondents; the qualities of managers that female and male managers lack; the presence and causes of gender discrimination; and “stop-factors” of career for men and women. It was found that female executives twice as often as male executives face gender discrimination; women more often than men consider their personal qualities as the reason for career success (men more often than women cite external aspects such as “mentor” and “good timing” among the reasons for career success). At the same time, experts noted that “the boundaries of “female” and “male” qualities are blurring” (Forbs, 2021). In our opinion, this is also due to the influence of digitalization, which is changing the content of many areas of activity.