With the development of digitalization and especially after the COVID-19 pandemic, remote work and freelancing are confidently being introduced into our lives. Notably, journalism is one of the most popular areas for freelancing. Freelance journalists balance between instability and autonomy, highlighting both the advantages and disadvantages of this way of earning money. The author of this article analyzed 200 materials from open sources (essays, blog entries, posts on social networks and interviews) covering the problem of professional rise and development of an individual media freelancer plus the results of the conducted expert surveys. The purpose of the study was to find out how successful freelance journalists really are in modern Russia, how stable and high their income is, what methods they use to find new contracts, what their attitude is to income diversification and the need to keep accounting, and, ultimately, who they feel like: employees or entrepreneurs. The results of the study demonstrate a high level of satisfaction with freelancing, despite the presence of financial difficulties and the need to take on entrepreneurial risks. © 2023, MSU Publishing House. All rights reserved.