Contemporary work increasingly presents itself as an immeasurable endeavour. The social and subjective spaces in which it is practiced are no longer easily circumscribed, and the conceptual categories that traditionally described its relationship with value now appear practically unusable. In particular, workers in the ‘creative industries’ are paradigmatic subjects of the ‘work fragmentation’ process of the post-Fordist era. Cutting across divisions between life and work, employment and unemployment, the performing arts are in many ways a laboratory of job flexibility, where innovative contractual arrangements and professional trajectories have been developed. In this article, we have mapped the multiple forms that work has taken in the last two decades in Italy. The empirical data is derived from a combined method that utilizes both quantitative surveys and in-depth interviews with artists, technicians and organizers working in the fields of theatre, music, dance and video making. A central feature of the new regulative conditions, and therefore the experiences of these professionals, is the new relationship with time and, more specifically, the ‘loss of measurability’ of hired labour. The aim is to provide a multilayered analysis of the interactions between the socio-economic conditions, career pathways and cultural aspects, i.e. the expectations, reputation, self-perception and social recognition of these jobs. Accordingly, these work patterns are studied as self-employment strategies based on the diversification of activities and expertise, and at the same time, attempts to devise new spatial and temporal configurations of labour, epitomized by the hybrid condition of the ‘salaried employer’. In these cases, precariousness emerges as a generative terrain of ambivalent subjectivities. On the one hand, the workforce is spontaneously mobilized and autonomously organized by the realization of desires, expression and self-fulfilment, beyond mere economic rewards. On the other, the labour itself becomes increasingly intertwined with ones life, as well as becoming immeasurable. Time loses its function as a unit of measure for compensation (i.e. as in work for a flat rate). This situation frequently leads to the spread of labour into other spheres of life and the risk of self-exploitation. To conclude, the new experiences of union organization and social movements, manifesting in the occupations of theatres, are examined as spaces where differing, and even opposing, solidarity and ‘class composition’ practices within the new creative labour(s) are experimented.