Aim: The present study aimed to understand the lived experience of the challenges of working beyond retirement age among employed older Iranian men. Methods: This qualitative study employed van Manen's hermeneutic phenomenological approach in 2026. Participants comprised 16 employed older adults aged 60 years and over in Tehran, selected through criterion-based purposive sampling. Data were collected using the Abbreviated Mental Test (AMT) (to assess the inclusion criterion) and individual semi-structured interviews, and were analyzed through three readings—holistic, selective, and detailed—with the assistance of MAXQDA-22 software. Results: The phenomenological analysis revealed that working beyond retirement age is a multidimensional and tension-laden phenomenon manifested in seven essential themes: pervasive economic pressure and livelihood insecurity; heavy psychological strain, ranging from fear of enforced idleness to despair; embodied exhaustion and gradual physical decline; intergenerational gap and conflict; structural critique and longing for emancipation; meaninglessness and lack of job satisfaction; and restricted leisure coupled with the necessity of regulating work. These challenges were distributed across van Manen's four existential dimensions: lived time, lived space, lived body, and lived relation. Conclusion: The challenges of working beyond retirement age are not the product of ageing per se, but rather the product of the interaction between ageing and occupational, economic, and organizational structures. Effective policymaking should simultaneously focus on strengthening pensions and housing support, facilitating part-time and age-appropriate employment, promoting occupational health among older adults in physically demanding jobs, and activating the intergenerational transfer of experience.