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This article aims to analyze how the so-called ‘pedagogy of work’ attempts to answer the challenges of unemployment and job insecurity characterizing the labor market in contemporary society. The authors reflect on the concepts of nihilist pedagogies and the ‘end of work’ by distinguishing two approaches: an active and a passive nihilist pedagogy. The passive approach, based on resignation, is opposed to an active attitude in which labor pedagogy offers tools to address current challenges. The authors support the idea that pedagogy as a human-improving science cannot adopt the position of passive nihilism in interpreting work in contemporary society. To better understand the dynamics related to job insecurity and corrective solutions by pedagogy, the authors analyzed the thoughts of three contemporary philosophers: Zygmunt Bauman, Jeremy Rifkin, and Dominique Méda. These authors redefined the concept of work in connection with the transformations because of globalization, the advent of new communication technologies, and digital work. These changes have redefined not only the concept of work but also the models of work pedagogy in the Western world: capitalism and Marxism. Considering the current challenges, the pedagogy of work needs to be rethought, starting from the problem of employability and focusing on the new occupations in demand in the Internet age. By integrating ideas on interpreting work from the theories of Bauman, Rifkin, and Méda, it is possible to propose a pedagogy of work in the age of change and to outline possible values of education inspired by it.