South Working is an initiative that reconciles the need to stem the depopulation of Italy’s South and the internal areas of our peninsula with an authentically lean conception of work, from the perspective of guaranteeing an economically, socially, and territorially sustainable future and offering a solution to the age-old problem of territorial differences. In the implementation of smart work and telework, the pandemic played a fundamental role as an incubator, that forced companies not only to adopt measures to reinvent in-person work, but also to experiment with and recognize the potential of alternative and traditional methods. The experience of instituting remote work and “community facilities” can also be a tool to bring back part of the human capital lost by depopulated territories. Together with opportunities, it is also necessary to look at the challenges and criticalities of the project in light of the current national and international situation: precariousness and financial uncertainty, relations with local governments, institutions, and various stakeholders, as well as problems relating to infrastructure and welfare. Among the solutions proposed to face these criticalities are the promotion of shared work spaces, the creation of new professions (such as the community manager) and a renewed attention to regulations on smart working.