For today’s knowledge workers, the boundaries between work and private lives are eroding. We can now work anywhere and anytime: at Starbucks, in the checkout line at Whole Foods and by the pool during Spring break. While at work, we may play Pokemon Go, go running or catch a nap. As our schedules are becoming unique imprints of our lifestyle choices, our buildings  and neighborhoods need to become flexible enough to accommodate conflicting needs where one building occupant may go for a blue-light fix along with a double shot espresso while her colleague opts for low color temperature lighting and herbal tea. What role is left for daylighting design when occupants’ needs are trailing out of sync with natural lighting cycles? How do we design resource efficient neighborhoods when it is not even clear where resident will be when? Drawing on recent work at the MIT Sustainable Design Lab on urban level environmental performance analysis regarding building energy use, daylighting, outdoor thermal comfort and building integrated agriculture, this presentation demonstrates how the resulting tools can be productively used at the interface between architecture and urban planning and reflects on what types of new urban living may emerge from these design explorations.