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This article deals with a little explored field: the links between addictive behaviors (with and without products) and unemployment, explored here through the analysis of crossed trajectories of work and health. To this end, qualitative research was carried out in partnership with several institutions and associations supporting job seekers. In this article, we give priority to data collected during individual semi-structured interviews (108) with unemployed people, exploring the diversity of uses rather than the disorders linked to them, the weight of the trials, and the contexts of work and unemployment. The diachronic analysis of the processes leading to the use of psychoactive substances (PAS) at work, and then in unemployment, allows us to differentiate the functions of the recourse to addictive behaviors, to identify the modes of entry into and exit from these behaviors. The recognition of the experience of users and their strategies to regulate their consumption opens both to a systemic analysis of the work context and to the conditions of an authentic health work at work as well as in unemployment.