The transition from socialist state to market economy caused inequalities and social stratification in most Former Soviet Union countries, but especially in Russia. The economic and social changes in Russia have led to insecure and individualized situations for most of the young people. The choices of young people in Russia are strongly shaped by the socio-economical and political transformation which unequally distributed the chances of young people to prosper or at least to have equal opportunities in education, leisure activities, mobility, and medical care. Moreover, the place of residence, namely large cities, small towns, or rural areas, defines economic opportunities, as well as educational opportunities, diversity of leisure activities and choice of social services and medical care. The paper gives insight into the life chances young Russians see for themselves under these conditions of insecurity. 16 problem-centred interviews were conducted with adolescents at the age of 15-18 in the Leningrad and Novgorod regions and in Saint Petersburg and have been analysed using the Capabilities Approach of Martha Nussbaum as theoretical framework.