This article explores personal assistance from the assistants' perspectives. Many assistants are satisfied with their work and the possibility to combine the work with other activities on a flexible basis. However, the structural framework of the personal assistance scheme creates risks for the workers who carry out the assistance. These risks are related to strong user control, intimate and personalized relations, part-time work, weakly formalized working conditions and few chances to gain qualifications for future employment opportunities. The gendered labour market is also a structural condition of the scheme. The article focuses on three theoretical working life discussions: flexibility, professionalization and co-determination (between service user and assistant). The article reveals the specific and inverted form these processes are transformed into by the personal assistance scheme and suggests that they create barriers for sustainable working conditions for the assistants as well as options for developing solidarity between service users and assistants.