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This paper assesses the dimensions of enterprising tendencies and retirees’ income earned from income-generating activities. The study used a cross-sectional research design. Accordingly, quantitative and qualitative methods were used for data collection. Questionnaires and an interview guide were administered to 80 retirees obtained by using snowball sampling in Dodoma, Tanzania. Descriptive and regression analyses were conducted to generate meaningful information. The results of the study show that an individual retiree's economic well-being is improved by locus of control, need for accomplishment, risk-taking, and innovation in enterprising tendencies. The findings revealed further that retirees in Dodoma City have a low enterprising tendency (a score less than 3). On the other hand, retirees perceived difficulties as negatively influencing their economic well-being. Thus, inculcating an entrepreneurial culture is considered essential not only before but also after retirement. Retirees are advised to have confidence in their capabilities as far as enterprising tendencies are concerned.