Historical analogies of environmental change and stress are a well-established method of examining vulnerability to the impacts of climate change. In our view historical analogies of social transformations can similarly illuminate what factors are conducive to transformation. In this paper we draw on the historical example of the environmental transformation of Aotearoa New Zealand from predominately woodlands into farmlands; a transformation which was inextricably linked with the social transformation of indigenous Māori society following European colonisation. The Aotearoa New Zealand case study illustrates how both incidental and purposeful transformations can be instigated by small groups of committed individuals working in formal or informal networks, but can also be imposed by outside experts who instituted widespread changes under notions of progress and improvement without local support or consent. Such transformations involved widespread changes to Indigenous governance regimes, agricultural systems, production and consumption patterns, lifestyles, values and worldviews, and inevitably involved both beneficial and negative outcomes for local peoples. We argue that thinking historically about transformational change provides an opportunity to assess the processes that shape both vulnerability and resilience, and the circumstances under which transformational change occurs, as well as the potential dangers of irreversible changes.