Drawing on pragmatic and occupational sociology, this paper examines how individuals in Sweden embark on occupations that are in nascent stage and for work tasks that are weakly defined. I accompanied a group of aspirants as they moved from a higher vocational education programme into the labour market, following their learning journeys towards emerging occupational roles. The present paper focuses on how they face reality tests related to their unclear occupational futures and the navigation of ethical grey zones when in the labour market. These tests occur in transition from education to work, and particularly for emerging occupations, due to the uncertain and fragile logics that surround new work tasks; in this case, offering digital data services. Through encountering these tests, aspirants are offered the opportunity to negotiate and develop moral competence, although they vary in their coping strategies. The findings of this analysis set out to contribute to the literature on how individuals are prepared for emerging occupations and propose the concept of 'weak-form occupations' as a means to characterise and examine education to work pathways that are less intuitive or predictable.