Although the socio-political development in the 20th century gave rise to humanity’s commitment (at the very least a declarative one) to the promotion of human rights, at the same time doubts about tangible enforceability of economic and social human rights are intensifying. Even though all human rights of the second generation are vague and undefined to a greater or lesser extent, the right to work is probably the least understood among them in terms of meaning, scope, and reach. The above may seem inconsistent with the fact that the value of human work has been recognized and praised since the time of the ancient philosophers, as well as with the fact that in many cultures and societies work is considered paramount in promoting human self-esteem and human dignity, a proponent of faith and social integration, and a source of respect from one’s social milieu. Freely performing meaningful actions is a prerequisite for a life that does not consist exclusively of mere survival, but paid work is primarily the main means of combating economic deprivation through the acquisition of property and the utilization thereof. Taking into consideration this contrast of the importance of work and the simultaneous numerous ambiguities accompanying the very institute of the right to work, the purpose of this paper is to study and evaluate the historical and current state of the right to work as a human right, to recognize certain transformative forms of work and some of possible substitutes for work and to understand the future of this human rights instrument. Unfortunately, despite the general development of human rights, the emergence and expansion of trade union organizations and codifications of the idea of work as a guarantee of a dignified life in numerous international treaties and national constitutional or legal texts, this specialist paper will show that the positive right to work has poor chances of becoming a fundamental human right even with the best effort of all stakeholders involved in the labour market, but with the large and powerful political, economic and technological factors acting in opposition to the idea this prospect becomes downright impossible.