While innovative approaches to urban transformations are increasingly proposed, scholars often overlook challenges faced by endogenous actors (e.g. urban planners) tasked with taking action within non-ideal, real-world settings. Here we argue that an ‘inside’ view of transformations (focused on judgment in practice) is needed to complement existing ‘outside’ views (focused on assessment), where the feasibility of action becomes a central concern. This recasts urban transformations in a discretised perspective. It suggests a view of transformation pathways as both directed and stochastic, and emergent from an unfolding series of ‘fuzzy action moments’. Principles for bridging urban science and planning are derived.