Ubiquitous digitalization and the coronavirus pandemic have made freelancing a familiar part of our lives. Journalists are no exception. Moreover, the media sphere is one of the most popular for freelancing and remote work. However, freelancing is not only about changing the location of an employee. This is a completely different format of relations: from an economic, legal, psychological, creative, and other points of view. For many freelancers, this is a way of life and a different type of thinking. Taking into account the process of media convergence and the popularization of new media, the boundaries of the journalistic profession are blurring and include specialists who are far from traditional journalism. There is also a question of freedom of journalistic creativity: many freelance journalists choose this path for the sake of autonomy, although entrepreneurial risks and economic challenges often undermine the independence they have gained. We analyzed 200 texts from open sources on the topic of the start and development of professional activity of freelance journalists, adding the results of personally conducted surveys. As our research has shown, despite the economic instability that often forces freelance journalists to immerse themselves in related activities, the requirements of digital algorithms that set strict limits for authors, and other problems, the issue of creative self-realization still occupies an important place in the work of freelance journalists, and many of them are not ready to put up with uninteresting and meaningless tasks. Although some freelance journalists agree to write on any proposed topic for the sake of a fee, most consider it necessary to have a specialization in order to deeply understand the chosen field.