The 21st Century’s phenomenon that is most notable in European countries is a shift in the structure of employment to self-employed without employees within gig-economy and information technology. This type of self-employed increasingly influence the pension system architecture through unregular contributions, gaps in the insurance biography, pension care coverage reduction. Due to the newness of this question the previous investigations in this field are limited in numbers. In that context, a comparative analysis of the size and structure of self-employed in Russia and EU countries is carried out, their revenue potential for pensions is evaluated. Effective architectures of pension system for self-employed in developed EU is investigated. Conclusions and proposals for Russian pension system are made.