On the basis of a qualitative study, the paper examines the conduct of life of middle age solo-self-employed workers (self-employed without employees). The title-giving “life in the subjunctive” is derived from the statements of the persons interviewed, who permanently refer to what they would theoretically have to do – without, however, actually doing it. At the same time, the use of the subjunctive reveals a permanent need for action, which threatens to paradoxically turn into a peculiar state of paralysis. The subjunctive is thus to be understood not only as a linguistic form but as a coping pattern which reveals the structural challenges and limitations that solo-self-employment exerts on its subjects. Against the background of destandardization and flexibilization of life courses and work, solo-self-employment is presumed to presage new working and living conditions, which are linked to the current regime of the self and the value of autonomy and personal responsibility. Referring to the analytical category of age, the article identifies limits on the invocation of a seemingly ageless “entrepreneurial self” and the notion of a continuous and stable “midlife”.