Purpose of the Study: This study aimed to investigate the operationalization of Jitegemea Philosophy as a model for the sustainable development of retirement plans among pulpit workers. Statement of the Problem Despite the importance of retirement planning, these workers face challenges such as low salaries, irregular income, and limited access to pension schemes, leading to financial insecurity in later life. The Jitegemea (self-reliance) philosophy, rooted in principles of self-sufficiency and sustainability, offers a potential model for addressing this gap. However, there is limited research and practical application of Jitegemea as a structured retirement planning model tailored to the specific needs of pulpit workers. Addressing these challenges is crucial to ensuring the financial security and well-being of PCEA pulpit workers in retirement. Therefore, this study explores how operationalizing the Jitegemea philosophy could provide a sustainable solution for enhancing financial security and well-being for clergy during retirement. Methodology: This study employed a qualitative research approach, utilizing semi-structured interviews with PCEA pulpit workers to explore their perceptions, experiences, and challenges related to retirement planning. A purposive sampling technique was used to select participants from various PCEA churches in Nairobi. Data were analyzed thematically to identify key themes and patterns related to retirement planning among PCEA pulpit workers. Key Findings: The study revealed that while many clergy face socio-economic barriers, religious beliefs, community support, and proactive planning can foster resilience. Participants expressed mixed emotions about retirement, some feeling apprehensive and others viewing it as a period of spiritual renewal. The study highlights the need for tailored support mechanisms, including financial literacy programs, fair compensation, and expanded pension schemes. Conclusion: The study emphasizes the importance of collaborative efforts among religious institutions, policymakers, and community organizations to improve retirement planning. Recommendation: Recommendations include financial education, compensation reform, and community support to ensure better retirement preparedness. Further research is suggested to evaluate the long-term effects of these interventions on clergy retirement outcomes.