This paper explores a little understood aspect of education labour markets, the tendency for teachers to simultaneously engage in both white-collar side-hustle and blue-collar or land-based entrepreneurial activities. The papers argues that teacher’s engagement in multiple activities such as moonlighting and agriculture in rural community enhances their income and this helps to compensate for wage differentials with their urban counterparts. This practice is also associated with teacher retention and community integration of teachers which is a common challenge relating to rural school staffing. We suggest that the phenomenon of non-education related teacher side-hustles, which are typically understood to be problematic, is a more complex issue and a practice which may have potential benefits for hard-to-staff schools.