In political decision-making processes in Greenland, comparisons are often drawn with Denmark, Scandinavia, the Faroe Islands, and Iceland. With Greenland as a case, this article analyses a series of aspects across the societies to highlight the politics of comparisons, which are taken for granted, and to emphasise contextual conditions. Comparisons are central to cultural meaning-making and navigation with nation building strategies. We conclude that the current comparisons are significant in terms of explaining Greenland’s challenges with a vulnerable economy and with the sustainable use of natural and human resources. To utilise local resources and create a sustainable livelihood, there is a need to break from the existing trajectories based on the current politics of comparison to explore local conditions more carefully and find other models of inspiration. By developing the concept of island operation, the article unfolds distinct characteristics of the Greenlandic socio-economic structures and includes statistical data on trade, education, and the labour market to support the identification of conditions that can contribute to future analyses of Greenland’s sustainable development. This analysis has relevance for societies that share geographical and cultural conditions with Greenland and post-colonial countries that must deal with complex path dependencies to navigate towards sustainable development.