The unquenched thirst for emigration in Nigeria and the increasing cost of migrating to the West has been established in the literature. Professionals, such as healthcare workers (HCWs), are poorly paid in Nigeria, making many seek better employment abroad. However, many professionals work in less skilled sectors or jobs below their previous position—and education and years of experience—in their home country. While studies have investigated occupational deskilling empirically from the experiences of migrants in the host country, this study focused on HCWs who are still in Nigeria but expressed emigration intentions. This allows us to understand whether migrants are victims of occupational deskilling in the host country or whether it is a calculated decision. We investigated the willingness among HCWs in Nigeria to accept occupational deskilling post-migration. Using a cross-sectional online survey, we analysed responses from 411 respondents who indicated emigration intentions. We computed logistic regression models at a 95% level of significance. We found that 65.3% of healthcare workers reported willingness to accept occupational deskilling. Male HCWs were twice as likely as their female counterparts to accept occupational deskilling, and pharmacists were 16 times more likely to accept it than medical doctors and dentists. Work hours and job satisfaction were also significantly associated with the acceptance of occupational deskilling. We submit that, in the case of Nigerian HCWs, migrants are not necessarily victims of occupational deskilling; their decisions could have been calculated, which resulted in the impression that working in the less skilled sector in the West is better than working as an HCW in Nigeria.