Sometimes we need to stretch the conventions and assume different perspectives to see other futures. In Fall 2015, MAS Studio designed the exhibition BOLD: Alternative Scenarios for Chicago as part of the first Chicago Architecture Biennial. The exhibition invited the public to explore architectural and urban planning alternatives for Chicago; the physical and intellectual opportunities that lie between the seemingly rigid constraints and conventions constructed in the city since its foundation 179 years ago. Just as we have come to appreciate the efficiency of the orthogonal grid that organizes Chicago, we have become used to the graphical representation of time passing on a straight horizontal line.