This chapter unpacks the new information-based toolbox of the contemporary architect and urbanist. Tracking innovations in computational design which now enable metric, data-driven methodologies, the potential for building associative logics in design models and for the city is explicated. Parametric and algorithmic methodologies are powerful tools for generating organizational heterogeneity and spatial variation and differentiation. It is the proliferation of interfaces and control systems which has led to the development of performance-oriented simulation and feedback systems. Today's lifelike and intelligent design environments have parallels with gaming interfaces and environments. Targeting, for the future, multiple design options with differentiated trajectories, we may in the twenty-first century develop greater capacity to adapt to and manage change.