Examples of topographical enquiry embedded within transitional urban settings in India and Sierra Leone are reviewed. We show how place-curiosity and embedded enquiry is necessary to initiate an appropriate iterative process of making, which has resonance at a range of scales from the bottom upwards. The chapter is divided into two sections. In the first section, we review how acting as a detective in Delhi and Agra, students discovered the rich interplay between culture and physical landscape in the dynamic city: we uncover fragments and dormant resources highlighting relevant issues and concerns. In the second section, acting as a storyteller in Freetown, Sierra Leone, we give an example of institutional scaling from the bottom up. We show how the resolution of some issues and concerns, uncovered during a school building project, were employed to construct a well-fitting narrative leading to firm proposals for making projects at the city scale.