Efficient functioning small businesses and their continuance over time, independent of the owner(s), carry high significance for remote regions' long term social and economic sustainability. This empirical investigation of exit planning practices among regional small businesses in the New England region of New South Wales, Australia, provides evidence that the particular environment in which these businesses operate determine and drive owners' strategic exit planning initiatives. Regional SMEs are prone to peculiar internal and external variables with inertial forces that continuously impact on the owners' decision to exit or continue into the business. Resorting to Schatzki's (2002) 'site of the social' theoretical construct, this paper argues that the 'exit planning' social practice among regional SMEs can be efficiently developed and institutionalized at a wider level on their peculiar 'site' of being regional and small. Thus, a borrow from the 'specialised clusters' technique on the part of State government is the best way forward to effectively tackle the phenomenon.