Singapore has an age-based mandatory retirement policy for taxi drivers. In 2006, the upper age limit of mandatory retirement was raised from 70 to 73 years for healthy, older taxi drivers. Retirement from taxi driving in Singapore often results in simultaneous retirement from work and forced driving cessation due to limited private vehicle ownership. While both retirement from work and driving cessation have been found to have negative implications for health and wellbeing in Western countries, little is known about the effects of mandatory retirement and driving cessation for healthy professional drivers in an Asian context. This study aimed to explore the mandatory retirement experience of older Singaporean taxi drivers, aged 70–73 years. In-depth interviews were conducted within a descriptive phenomenological approach with 23 older Singaporean taxi drivers who were retired or retiring drivers. Findings showed the experience to be dominated by retirement from work issues rather than by driving cessation. Three themes described the experiences: ‘stories of taxi driving’, ‘feeling lost in retirement’ and ‘contradictions of growing old in Singapore’. Taxi driving was a valued role. Despite an expected retirement, most participants were not prepared for the retirement transition. They struggled with emotional adjustment, financial vulnerability, identity, reduction in life-space and meaningful activity participation. Participants felt under-valued despite having personal achievements and support from family and ‘successful ageing’ policies. Work remained a preferred activity despite limited re-employment opportunities. The unique context of expected but forced retirement, financial need in a non-welfare system, high cultural value on work, and limited options for productive or meaningful activities and roles, predisposed this sub-group of older Singaporean men to be vulnerable retirees in terms of identity and wellbeing issues. Support for a stressful late-life transition is indicated for continued health and wellbeing.