Images of what retirement is and ought to be are changing. Older workers are being encouraged to work for longer, at the same time, older adults increasingly voice expectations of a ‘third age’ of active engagement and new life prospects. In this article, we draw on the literature on older workers’ work patterns and retirement transitions (noting push/pull/stay/stuck/jump factors), and on scholarship on the changing social meaning of old age, most importantly the notions of a ‘third’ and ‘fourth’ age. The analysis is based on qualitative interviews with 28 employees in the private sector in Norway, aged between 55 and 66 years. Based on the interviews, we propose three ideal-typical approaches to the work–retirement transition: ‘the logic of deadline’, ‘the logic of negotiation’ and ‘the logic of averting retirement’. The ideal-types are defined by the degree to which informants assume agency in the workplace, their orientation towards work versus retirement and the degree to which they expect to exercise agency in retirement. We emphasise how retirement decisions are informed by notions of the meaning of ageing, while also embedded in relationships with employers and partners.