As global demographics shift toward an ageing population, ensuring retirement financial well-being (RFWB) has become a critical policy and socioeconomic concern, particularly in developing countries like Zimbabwe. Amid an inflationary economic environment, retirement financial planning is increasingly exploring digital entrepreneurship as a pathway to sustain financial security in post-work life. Using a qualitative research method, this study investigated how artificial intelligence (AI) can support retirement financial well-being by enabling digital entrepreneurial activity while also exploring the interplay of cognitive, emotional, and financial factors influencing such engagement. Grounded in the Holistic Financial Wellness Model, a qualitative research method was used with data being collected using semi-structured interviews. A sample of 176 academic staff was selected from higher education institutions in Zimbabwe using convenient sampling. Purposive sampling was used to identify 59 key informants comprising of deans, academic registrars, human resource practitioners, as well as finance lecturers. Content analysis using NVivo15 software identified three themes: namely, cognitive ability, emotional, and financial factors. Financial education was found to focus more on grooming students for future employment rather than for making personal financial decisions. Digital financial education was found to be lacking in most finance programs, bringing attention to the need to incorporate AI-simulations in the finance education curricula. Digital financial literacy was found to be high for low-complex routine transactions but low for high-complex long-term financial decision-making, negatively affecting the use of digital platforms for financial retirement well-being preparedness. Perception of digital entrepreneurship, the use of AI and digital platforms was found to be notably affected by age, with the older respondents expressing discomfort with engaging them as financial retirement planning tools while the younger respondents appreciated their flexibility and convenience. The interdisciplinary approach contributes to theoretical development on financial retirement planning by exploring cognitive ability, emotional, and financial factors’ effect on retirement financial well-being preparation within the paradigm of digital transformation. The need for a national framework guiding digital entrepreneurship, taking into consideration tax implications as they trade across geographical boundaries, was identified and recommended. A gap in the current financial education programs was noted as they do not included digital financial education.