The core trends in modern digital transformation are the disintermediation and advance of digital platforms. In the particular area of labor and entrepreneurship, these phenomena lead to the emergence of hybrid forms of employment, own-account work through digital platforms, and the transformation of the labor relationship into self-employment. Thus, the employer is being excluded from the relationship, and the consumer takes his place. The digital transformation of labor is giving rise to a new type of economy - the gig economy. The purpose of the presented article is to identify the factors of the digital transformation of labor into self-employment. As a part of the total solution, the following research tasks have been completed: the concept of the gig economy has been identified with the subsequent targeting of the trends that affect digital transformation at the confluence of hired labor and entrepreneurship; the particular area of self-employment resulting from the digital transformation of labor and individual entrepreneurship has been identified as a subject of research; also the legal and technical outline of the digital environment of self-employment has been studied.