The article deals with symbolic representations of St. Petersburg residents about the Soviet and post-Soviet societies, obtained by the associative method with subsequent content analysis. Comparison of survey data from 1996 and 2014 allows us to identify the dynamics of both ideas and the content of the image of modernity. The article reveals the conditionality of concepts and assessments by belonging to a certain generation of “Soviet people”, “Soviet children” and “post-Soviet people". Special attention is paid to the impact of the return of Crimea to Russia on the perception of modern Russian society and the state.