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This paper takes the form of a deeply personal narrative, relating the story of how early community activism prompted a career of over two decades in urban planning in a post-apartheid metropolitan Council in South Africa. It shows how a sense of frustration with a system that was unable to facilitate the spatial restructuring of an unequal urban form, prompted the transition towards becoming a critical researcher within the local state apparatus. It reveals how attempts to speak truth to power through research that could uncover unexplored complexities, contestations and dubious local state practices, whilst still in the employ of the institution was at best, challenging. Through the use of real examples from planning practice, the paper unpacks and carefully documents four key considerations that make such embedded research difficult. In sharing the lessons learned from the aborted research project, it then suggests what type of research is possible by picking up the story of a second attempt at "safer research". It wraps up the story with new insights, this time from a perspective as a recent-outsider — not as a stranger though, but as one of the local state's own. Whilst appreciating the value of distance in undertaking research, it speaks to the power of familiarity and trusted ties, and the legitimacy that comes with being a credible outsider. At the same time, it also reflects on the possible challenges associated with being such an outsider. Through critical reflection on the process of doing research inside and outside of the local state, the paper suggests that differential positioning can significantly affect the depth of insights around state practices in urban governance. [ABSTRACT FROM AUTHOR]