Purpose: The paper aims to explore "Portfolio work", an emerging form of flexible self-employment, which has been identified as significant but under-researched. This paper also seeks to explore the challenges and benefits of portfolio work from the perspective of individuals' experiences. Design/methodology/approach: The argument draws from a qualitative study involving 31 individuals practising portfolio work in two different occupational groups: nurses and adult educators. Participants were interviewed in semi-structured in-depth conversational interviews to explore their everyday experience and work history in portfolio work. Findings: Two dimensions of portfolio work, work design and client-relations, are found to generate experiences of both deep satisfaction and deep anxiety and stress. The paper argues that portfolio careers simultaneously embed both liberating and exploitative at dimensions for workers, which are at least partly related to their own conflicting desires for both contingency and stability. Further, portfolio work embeds labour that often remains unrecognized, even by the self-employed individuals assuming responsibility for it. Practical implications: Portfolio workers need to recognise and document their unpaid but necessary labour in work design and client relations that sustains their careers; portfolio workers may need to educate clients about the nature of portfolio work; and employers who contract to portfolio workers must take more responsibility for negotiating fair contracts that are sensitive to overwork and unfair time pressures, and that anticipate and compensate contractors. Originality/value: These findings challenge existing conceptions of portfolio work as either exploitative or liberating, and expose contradictions embedded in both the conditions of the work and individuals' expectations and attitudes towards it.