The decision to start a new career might seem an unusual one to make in later life. However, England has seen a steady rise in numbers of workers undertaking an apprenticeship in their fifties and sixties, through a government-funded policy initiative opening up training to adults at all stages of the lifecourse. At the same time, in most Western contexts, the amalgamation of ‘older’ and ‘apprentice’ presents a challenge to normative understandings of the ‘right age’ to undertake vocational training. What is it like to make a new start as an older worker? This paper draws on new qualitative research conducted in England with older apprentices, exploring how they found the experience and management of training ‘out of step’. Inspired by Elizabeth Freeman's temporalities approach, our findings reveal how powerful norms of age-normativity routinely structure understandings, experiences and identities of older-age training for both organisations and apprentices. While these norms demand careful negotiation by both apprentices and trainers, if managed successfully older workers gain significant benefits from their training. These findings have resonance not only for England, but for other international contexts considering expanding vocational training into older age. The paper concludes that if adult training schemes are to succeed, some fundamental changes may need to be made to understandings of age and ageing within contemporary workplaces.