Political philosophy David Estlund has remarked that political philosophy suffers from a case of “utopophobia” or “the unreasonable fear of utopianism.” This paper shows how two common critiques of utopia, one represented by the work of F.A. Hayek and Karl Popper and the other by Karl Marx and Friedrich Engels, are based on a misunderstanding of the concept. Furthermore, this paper goes on to demonstrate how utopianism is also implicit in the writings of these anti-utopian critics in several problematic ways. Following this analysis, this paper suggests that we can think about utopia in terms of a loose typology, evaluating any particular utopian vision on two dimensions: (1) its level of perfectionism compared to its openness to possibility and (2) the degree to which it is grounded in generally accepted empirical facts. Finally, this paper uses the City of Toronto’s laneway housing debate and the recent proposal from Google’s Sidewalk Labs to build a smart neighbourhood in the city to illustrate the need to explicitly discuss the utopian visions underpinning contemporary planning practices.