The article explores the current issues surrounding the operation of the self-employed sector in Russia. The legal frameworks for self-employment in various countries, including Germany, the United Kingdom, the United States, Japan, and France, have been examined in terms of taxation and social security. A comprehensive analysis of the legal status of independent workers in Russia has been carried out. The study examines the dynamics of this category over the period from 2019 to 2024, revealing a remarkable increase in their number, which amounts to more than 5,100%. The regulatory framework for the self-employed has been examined, which is based on the Federal Law No. 422-FZ of November 27, 2018, entitled “On the Implementation of an Experiment to Establish a Special Tax Regime: the Tax on Professional Income”. The advantages and disadvantages of the special tax regime are examined, including preferential rates of 4% and 6%, exemption from compulsory insurance premiums, limitations on annual revenue (equivalent to 2.4 million rubles), and prohibition on employing personnel. Proposals for improving the institution of self-employment in Russia are formulated: enshrining the legal definition of “self-employed” in legislation, introducing basic social guarantees, developing financial literacy programs, and expanding opportunities for hiring employees. The study has practical significance for the development of state employment policy and the legalization of the shadow economy.