The Netherlands is among the European countries with the largest increase in solo self-employment, whereas Germany has witnessed a much more moderate growth and recently even a decline. The chapter examines precariousness among solo self-employed in both countries and studies their behaviour and attitudes towards social risk. We use both unique comparative survey data and qualitative interviews. The question is addressed how solo self-employed deal with their insecure position. The findings indicate that financial resilience, social protection and (perceived) work uncertainty are often largely influenced by extant other sources of income (such as financial back-up) or expected sources of income (e.g. inheritance), which the self-employed take into account in their decision-making. Although some groups have adequately and ‘traditionally’ taken care of social risks and some have ‘alternative’ ways to deal with social risks, for a seemingly substantial group of solo self-employed social protection is a genuine sore point.