When planners began redesigning cities as machines, the logic seemed obvious. Efficiency, order, optimization: housing here, work there, traffic moving cleanly between them. It was the vision of architects like Le Corbusier, a city engineered to function. And for a while, it looked like progress.

Then something unexpected happened. Cities pushed back, not physically but socially. Neighborhoods lost their rhythm. Streets emptied out. Places designed for efficiency felt strangely lifeless.

That’s when Jane Jacobs looked at the same cities and saw something completely different. Cities weren’t machines: they were living systems. They worked because of small interactions, informal networks, and street-level judgment, thousands of human decisions happening every day. The life of the city wasn’t in the design. It was in the people navigating it.

As AI begins redesigning work as a system, it’s worth remembering what the cities taught us. Systems can organize work, but they can’t bring it to life. That part was never the system’s job.