Within the wide range of new forms of work self-employment seems to be a distinct feature concerning a growing part of the male and female labor force in industry and services in both Germany and the UK. Especially the growth of different forms of solo selfemployment is subject to pessimistic as well as optimistic interpretations of the future quality of work and life as well as gender equality. Sound knowledge on the extent and nature of this type of work, however is rare - our comparative analysis therefore seeks to highlight the development of solo self-employment and strategies of risk-management in Germany and the UK. Concentrating on the cultural industries as an emblematic section of the global new economy, it is based on a secondary analysis of national quantitative and qualitative data and on own empirical research. After an introductory summary of the main strands of scientific debate on self-employment, we will first present an overview of volume and structure of solo self-employment growth on the one side, and of social risks tied to this employment status on the other side. We will secondly highlight collective and individual strategies of risk-management from within a regulatory approach. The results of this analysis show that self-employment growth, though a cross-national phenomenon, displays nation specific characteristics if development in time, branch distribution, social risk, and gender are looked at. At the same time new ways of both individual and collective riskmanagement are emerging. These strategies, however vary in extend and sustainability, indicating an ongoing influence of different national labor market regulations and gender regimes.