The UK's population is ageing at a time when its oldest workers are leaving the labour market at progressively younger ages. This paradox - of declining economic activity rates among the 50 plus age group and rising longevity - has led to widespread concern over the social and economic consequences . Meanwhile, flexible work has grown in the UK economy and has been promoted as a promising solution to 'the problem' of older workers. Portfolio-type work in particular has been presented as a liberating option for the over 50s. Working for a range of clients, so the argument goes, would allow older workers to bypass barriers to employment in later life (such as company-specific early exit programmes), and would also allow them to negotiate their own transition into retirement. Yet there is a lack of research that examines the realities of portfolio working and its sustainability for people wishing or needing to remain economically active in later life. This study of freelancing among older workers was located in a sector where portfolio-type work was well-established: the media industry. It relied on in-depth, face-to-face interviews with 51 people who were actively engaged in freelance work as employers, individual freelancers and industry experts. The aim was to understand the conflicts, barriers and opportunities to freelance employment for those aged 50 years and over, using two contrasting perspectives, one provided by Nikolas Rose in his 'powers of freedom' thesis and the other by Margaret Archer in her 'morphogenetic' approach to realist social theory. The study found that freelancing did extend working lives and permit a degree of freedom and control in later life. However, it was a form of employment which was insecure, volatile and largely unregulated. The oldest freelancers were vulnerable to diminishing rewards, dwindling networks, dated skills and ageist attitudes. Age was found to be an important mediating factor in the experience of risk in the freelance labour market.