This article contributes to the debate about portfolio and organizational careers and presents the results of qualitative research of Russian young employees. During perestroika, Soviet career structures were almost completely destroyed. This led to the fact that working population of post-Soviet Russia had to adapt to new structures and/or create new conditions to be able to work and to ensure security. Such local uncertainty and instability coincided with intensive globalisation of the national economy and society, which had an even stronger effect: local instability combined with global instability.The analysis of biographical interviews demonstrated that a lot of young Russians on contemporary labour market can be characterised by portfolioability—a property that unites young professionals with different type of employment. We mean by this term a kind of attitude towards work typical for Russian youth, which reflects inner flexibility, experience, transferable skills and multiple employment practices. Moreover, it is portfolioability that in some cases becomes a resource to improve security/confidence concerning the labour market, as well as to develop agency. Besides, the lack of portfolioability results in a more vulnerable position and dependence on conditions.