This article explores the older worker discourse on wellbeing and work by highlighting the labour market re-entry and work experiences of a small group of older women who returned to New Zealand ‘rejuvenated’ after completing self-initiated expatriation (SIE), a period of extended travel and work overseas. The women explored a diverse range of organisational employment options and despite their intention to engage in appropriate and meaningful work pathways, their experiences were marred by discrimination, disadvantage and disappointment. However the participants, buoyed by the freedom, challenges and learnings derived from their recent SIE, were no longer prepared to compromise their personal wellbeing by engaging in unsatisfactory work roles and looked to alternative avenues, outside formal organisational work to preserve their sense of wellbeing. This research contributes to the older worker and wellbeing discourses by encouraging employers and other stakeholders to embrace a broad range of ‘older’ employee pathways, in a spirit of employer–employee reciprocity that support and enhance individual and organisational wellbeing.