The article extends notions of ‘active’ and ‘successful’ ageing by exploring the narratives of ageing in the retirement migration of Canadian and American older adults in Cuenca, Ecuador. The article is based on 83 semi-structured qualitative interviews (11 of which are follow-up interviews), most conducted in the first half of the 2010s. I explore how notions of finite time and imaginaries of a fourth age of decline and death inform the migration decisions and imaginaries of Canadian and American retirement migrants. I argue that their desire to seek self-expansive, new experiences through migration and contact with cultural difference dialogues with an increasingly competitive neoliberal culture of ageing, that emphasises success through activity, youthfulness and consumption. While there are certainly other ideals that help inform North American migration to Ecuador, I argue that these particular ideals illustrate how discourses of ‘active ageing’ have been taken up ‘from below’, by ageing North American adults, many of whom identify with the aspirations of policy and corporate discourses of activity and success, but who find themselves ageing into material conditions that preclude them. Migration to a lower-cost country, like Ecuador, helps them to experience these aspirations more positively, but may have uneven effects on lower-income workers and their ability to remain in place in the communities marketed for this type of migration.