The phenomenon of retirement is one of the most significant processes of individual role transition. If, during the stage of reflecting on one’s working life, an individual concludes that they have not experienced a successful career, they may consequently feel dissatisfaction with retirement. Therefore, the present study was conducted with the aim of understanding the nature of the lived experience of dissatisfaction with the retirement process. This research was carried out using a qualitative approach and employed a descriptive phenomenological method. The study population consisted of 213 retirees from the Fars Regional Electricity Company over the past ten years. From this group, 24 participants were selected through non-probability purposive (judgmental) sampling. Data were collected using in-depth semi-structured interviews and were categorized through qualitative thematic analysis. The findings indicated that the lived experience of dissatisfaction with retirement emerges as a set of interwoven themes, including dissatisfaction with the political environment, emotional dissatisfaction, identity-related dissatisfaction, dissatisfaction with executive processes, frustration with compensation, and dissatisfaction due to the underutilization of competencies. Additionally, the associated experiential meaning clusters included: political and factional relations, managers’ misperception of job positions, lack of attention to individual performance, acceptance of backstabbing and political deviation, political exclusion, type of employment relationship, changes in retirement laws, differentiated employment regulations, involuntary retirement, lack of professional empowerment, an instrumental view of human beings, عدم adherence to retirement formalities, lack of information and awareness about processes and regulations, dispersion in physical structure, security considerations, significant disparities in benefits compared to other companies, noticeable differences in benefits compared to the period of employment, unfavorable economic conditions, perceived discrimination, lack of succession planning, inability to transfer experiential knowledge, and instability in job positions. Each of these clusters was experienced by retirees across five contexts: political, legal, administrative, cognitive-perceptual, and economic.