Secure, full-time jobs that last until the statutory retirement age have dwindled. Meanwhile, flexible forms of work have grown and are increasingly promoted as promising solutions to the ‘problem’ of economic inactivity in later life. Government committees, campaigning groups and management authors have warmly embraced the possibilities of self-employment, contract work, freelancing, consultancy and part-time work for those who need or want to work beyond the age of 50 years. Portfolio-type jobs appear to offer choice, opportunity and control for individuals in the final stages of a career. Working for a range of clients, so the argument goes, allows older people to bypass age-discriminatory barriers to employment and negotiate their own transition into retirement, but very little research has examined the viability of portfolio work in later life. This paper draws on a three-year study of freelance employment in the British media industry. The aim was to understand the conflicts, barriers and opportunities involved in portfolio careers in later life. It applies a critical realist perspective. The study found that older individuals were vulnerable to job insecurity and financial risk because of their diminishing networks and skills. They experienced a reduced flow of commissions, which hampered their ability to exert choice and control in the labour market.