According to the psychology of sustainability and sustainable development, even though there are numerous challenges within the current labor market, it is possible to establish meaningful lives and meaningful work experiences through optimizing the use of personal resources and regenerating them. In line with this assumption, the present study aims to test the moderation effect of the type of worker contracts on the relationship between psychological capital, perceived employability, and job insecurity. Participants were N = 190 Italian young workers (self-employed, permanent employees, or temporary employees). Results showed that perceived employability mediated the relationship between psychological capital and job insecurity, and that this relationship was moderated by the workers' type of contract. Specifically, a higher level of psychological capital corresponded to a higher perception of employability, and consequently a lower job insecurity for temporary and self-employed workers, but not for permanent ones. These findings are in line with the assumptions of the psychology of sustainability, and encourage preventive interventions aimed to foster personal resources in order to reduce job insecurity, especially in cases of non-standard employment.