This paper aims to study the subject–work–organization relationship from the viewpoint of psychoanalysis. Modern organizations now demand a new professional profile. The subject struggles to deal with this new scenario, which offers him new possibilities to articulate enjoyment and desire. Which role does psychoanalysis play with regard to new challenges brought to the contemporary era? Is it possible to think of psychoanalysis as a way out of job-related dilemmas of Post-Modernity, or would psychoanalysis be risking establishing a pact with devil?