The relevance of this research is defined by the growing share of unreported employment and the need for elaboration of tax mechanisms, which would promote legalization of income that is currently not being taxed. The subject of this research is the taxation experiment on self-employed citizens. The goal lies characterization of the key vectors of taxation experiment on self-employed citizens, as well as development of proposals for assessing its efficiency. The author systematizes the norms the Taxation Code of the Russian Federation, federal and regional tax legislation, taxation statistics data, as well as outlines the changes to the experiment due to COVID -19 pandemic. The article provides an overview of the theoretical views of Russian scholars on the advantages and disadvantages of self-employment tax. it is proven that the current stage of the experiment can be considered successful based on substantial increase in the number of taxpayers and the volume of tax revenue. The scientific novelty consists in the development of approaches towards assessing the efficiency of taxation of self-employed citizens. The author proposes indicators that can be used for assessing efficiency of the experiment until 2028:  volume of tax revenue, number of taxpayers, number of tax disputes, tax arrears, amount of accrued dues, changes in tax revenue for other types of taxes that would replace self-employment tax.