International interest in freelance contracting as a distinct socio-economic phenomenon has been growing in recent years in the labour market and entrepreneurship literatures. Drawing on unique dataset comprising three waves of survey data gathered over a five-year timeframe, we shed light on the development of the Russian-language online labour market, which comprises freelancers from Russia and other transition post-socialist economies. Our findings reveal trends in the changing demographic profile of freelancers as well as important insights about their careers, work values and challenges. We argue that these freelancers represent a new generation of well-educated and motivated workers who are engaged in ICT and creative industries and are crucial for modernizing transition economies. However, the high levels of informality and client opportunism evident within the freelance economy constitutes an important socio-economic problem. By examining the experiences of freelancers in the context of transition post-socialist economies over a five-year period, we present new insights about the general traits and specific patterns of freelance contracting in the new economy.