The connection of educational systems with the labour market is an unavoidable issue of the development of educational systems and is particularly intensified in the modern times. Employers are often looking for evidence of attendance and completion of educational programs, social status is formed by possession of educational titles, salaries correlate with completed education level and so on. This higher "role" of education has gradually raised the question of quality of the same, which proved to be a fertile ground for various pedagogical theorists and thought revolutionists. Paolo Freire and Ivan Illich are recognized all over the world as fervent advocates of freedom in education and their vision served as the guiding thoughts that shaped this work. This final assignment examines the existence (or lack) of freedom in existing educational systems and reveals their shortcomings because of the same with special reference to the works and then to the legacy of Ivan Illich and Paolo Freire. By analysing their pedagogical work, as well as other literature that focuses on educational liberty, it is concluded that the lack of, and in particular the complete deprivation of freedom, has a very negative effect on the overall education and all of its participants, leaving permanent consequences not only on education but also on society as a whole.