Abstract This critical-reflective essay seeks to discuss the medicalization of performance based on reflections on flexibility in the world of work and the phenomenon of self-entrepreneurship. In a context of economy financialization, productive restructuring and State’s weakening as guarantor of social rights, precarization and informality are increasingly prevailing, where the promotion of labour flexibilization occurs in line with political-ideological strategies of neoliberal inspiration. There emerge ways of individualization tied to the construction of a multifunctional worker, available to develop multiple abilities, which becomes a potential enterprise and has as a principle the same market dynamics as this enterprise. The entrepreneur of the self needs to invest in itself to keep being valuable and having great functioning conditions, in order to avoid, to the fullest, its own decapitalization. Therefore, in order to enable conditions to sustain the image of success and of author of its own story, the usage of medicines, stimulants and multivitamins has been used as a strategy in search of high performance. To reflect on “the entrepreneur of the self”, the new ways of subjectivity and the suffering derived from those, as well as the apparatus that produces them, is necessary and consists in a challenge for community health.