The narratives on technological change and the emergence of the "fourth industrial revolution" (4IR) play a significant role in defining what has happened and is happening in the labor market. Those narratives, mainly based in developed countries, have served as a turning point for policy development, especially regarding the design and implementation of educational and labor strategies as policy instruments to cope with the challenges of inequality and its labor-related causes. However, the specificities of past labor and educational policies play a crucial role in understanding the possible effects of large-scale transformations related to technological change. In this research, I develop a theoretical model connecting the experience of the third industrial revolution, the current assumptions for the future of work agenda, the forecast regarding the possible impacts of the fourth industrial revolutions, and the areas for policy intervention. I use the model to craft a case study, where I present evidence regarding the evolution of the Chilean labor market between 1990 and 2020, following the evolution of job polarization, occupational composition, workforce educational attainment, economic complexity, and the technological ecosystem. I compared those elements with the stylized facts and assumptions of the narratives of technological change. I argue that the differences in the process of workforce adaptation (timing and material conditions) can shed light on the assumptions of the “future of work” agendas, especially by tackling how different conditions could reach different results and craft substantively different base scenarios for policy design and implementation of human capital-based interventions as the ones suggested by international organizations and forums. In the concluding chapter, I summarize the findings and comment on how to address the design of just labor transitions.