The digital age introduces fast-paced changes into all areas of our life. Technological progress has made it possible for a significant number of specialists to switch to remote work and freelancing, and the coronavirus pandemic has accelerated this process. Journalists are no exception, especially since the media sphere is one of the most popular for freelancing. At the same time, entrepreneurial risks, social insecurity, as well as the distance from the professional community entail psychological challenges, which, as current research and our analysis show, not every freelance journalist is able to successfully cope with. We analyzed 200 texts from open sources describing the beginning and development of the career of freelance journalists, and also added the results of personally conducted surveys. The results indicate that the majority of the Russian freelance journalists are satisfied with freelancing. At the same time, a significant number of them need additional methods to build personal-work boundaries, and also suffer from loneliness and professional alienation. Interestingly, Western researchers note the success of freelance journalists who are far from the traditional understanding of freedom in freelancing – those who use specialized workspaces and a time management system. However, among Russian freelance journalists, as our analysis has shown, those are more successful who, perhaps due to their temperament and formed habits, simply do not consider psychological challenges, existing for other individuals, to be a problem. At the same time, the percentage of those who face psychological problems in freelancing is high enough to discuss this topic and explore possible solutions.