Establishing a circular economy is assumed by some definitions to include social benefits such as employment opportunities; however, research beyond quantitative job creation projections is only recently emerging. While the repair sector is well-established, it has been suggested that increasing circularity implies significantly expanded demand for this service. This article uses five case studies of repair workers, based on semi-structured interviews, to explore self-employment in the repair service sector. Findings indicate that the stresses of work in the circular economy are similar to those of other fields, with self-employment offering opportunities both for job satisfaction and additional pressures. Research needs to give more consideration to the social implications of a circular transition—work may be a necessity for a satisfactory life experience (for most people), but it is under-ambitious to assume that having work is sufficient to achieve that, or should be the limit of ambition for a sustainability transition.