This project concerns the social enterprise SkyHands, which attempts to solve an inequality in time between busy families with too little time and unemployed flex workers with too much time. The project has its outset in a curiousity of which social challenges SkyHands can face in the realisation process. Our empirical data consist of two focus groups with a total of eight flex workers as well as semi-structured interviews with three families, the job centre in Roskilde and with Jane Markmann, the founder of SkyHands. Our theoretical framework is based on Bourdieu and his concepts of capital and habitus along with Goffman and his concepts of categorisation and stigma. In our analysis we point out that an essential task for SkyHands is to change the categorisations that are linked to flex workers, and through this convince the families to trust the flex workers and hire them for the jobs that the flex workers perceive as meaningful. We discuss the balance between structure and agency and how the two influence each other when defining meaningfulness. We conclude that the matter of SkyHands should be considered on both micro- and macro-level to achieve a nuanced understanding, and that the main social challenges Marckmann will face are the question of economy, prejudices and differing expectations.