Data from various sources indicate that the world’s population is aging and doing so at an unprecedented way. Global population figure of people aged 60 years and over have doubled since the 1980s. While these figures are indications of reduced fertility rate, improved life style, advanced medical technologies, there is also the school of thought that aging population pose as a challenge to the fiscal and macroeconomic stability of many countries. There is also another school of thought that argues that aged population also constitute an important part of the labour force or the labour market that have not been given much attention. Because people are living longer, older people are postponing retirement, hence, transitioning into bridge employment or grey entrepreneurship. Therefore, this study aims to develop understanding of how aging health workers transition to post-retirement work, in a comparative study. To answer this aim, a qualitative study was designed with the intention of developing a great understanding of the intensions and aspirations of health workers on their post-retirement career. Participants in this study were aging doctors and nurses in Sweden and Ghana. Data collection was done through the use of semi-structured interviews with open-ended questions with ten doctors and nurses each in Ghana and Sweden. The results show that almost all the respondents expressed the desire for a post-retirement career. We found that while every doctor in Sweden has the chance to participate in career bridge employment, it was only the specialized doctors that are more likely to have the chance to participate in career bridge employment in Ghana. However, almost all the respondents, except doctors in Sweden, expressed the desire for grey entrepreneurship, some have actually started their small businesses, for instance, one doctor owns and runs a non-governmental health delivery organization that delivers free health services to people in rural areas and in his community. To conclude, this study has shown that the desire and willingness of a post-retirement career especially in Ghana is influenced mostly by familial and economic factors, while personal factors explain that for Swedish doctors and nurses.