The digital Kowloon

What a walled city in Hong Kong can teach us about the future of AI development. And why vibe coding might be a regression to the 1990s, with better tools. There is a photograph taken in 1989 of Kowloon Walled City from above. It looks less like a neighborhood and more like a geological formation — a dense, irregular mass of concrete and rusted metal that grew not upward but inward , filling every possible gap until nothing remained but structure. No courtyards. No light wells. No logic. It is an image of what happens when human ambition operates without constraint, coordination, or shared vision. We are building its digital equivalent right now. And we are calling it innovation. An aerial photo of the Kowloon Walled City taken in 1989. The city that planned itself Kowloon Walled City began as a Qing dynasty military outpost on the Kowloon Peninsula - a garrison fort built in 1847. When Britain extended its lease over the New Territories in 1898, it left the Walled City in a jurisdictional gray zone — technically Chinese, practically ungoverned, and persistently overlooked by both sides. A patch of land that belonged to no one. As civil war consumed mainland China, refugees flooded into Hong Kong and found their way to the enclave. Later waves came fleeing the Cultural Revolution, joined by fugitives and those with reasons of their own not to be found. What drew them all was the same thing: a place that turned no one away. A postman in Kowloon by ©Greg Girard With no jurisdiction came no infrastructure. Electricity was stolen outright. Residents tapped illegal connections into the municipal grid outside the walls and ran cables across the buildings above. When officials discovered them and cut the lines, new cables went up over the dead ones. Then those were cut, and new ones followed. Layer upon layer, season after season, until the alleyways were canopied by a dense, chaotic web of wiring that no one fully understood. It was a record of every failed repair, every workaround, every solution built on top of a problem that was never actually solved. It was always easier to add a new cable than to make sense of the old ones. Residents built upward, floor by floor, without permits and without architects. New structures were bolted to existing ones. Pipes ran wherever they could. By the late 1980s, the city housed between 33,000 and 50,000 people on roughly 2.6 hectares — approximately 210 by 120 meters. Its population density reached approximately 3.2 million people per square mile: around forty-five times denser than Manhattan today. A temple inside Kowloon by ©Greg Girard And yet it functioned . There were restaurants, dentists, factories, schools. The city had a pulse. But it had no design. No one had ever asked: what should this place be ? Every decision was made locally, immediately, in response to the pressure of the moment. The result was a place of genuine human energy encased in a structure that could not be understood, maintained, or safely expanded. When Britain and China signed the 1984 declaration that would return Hong Kong to Chinese sovereignty in 1997, both governments looked at Kowloon and reached the same conclusion: neither side wanted to inherit it. When the wrecking ball finally arrived in March 1993, engineers found layers upon layers of undocumented additions, each one built in ignorance of what came before. A Kowloon rooftop by ©Greg Girard Before we discovered the user There was a time when the people who built software were also, by default, the people who decided what it should do and how anyone should use it. Not because they were the best qualified, simply because they were the only ones in the room. Software was planned and written by engineers, and the assumptions baked into those products reflected it. If you wanted to use a word processor in 1987, you first needed to understand how the word processor thought . The word processor didn’t have a WYSIWYG interface; menus were structured around system logic, and file managers reflected the computer’s directory trees rather than how a human might think of them. Error messages were written for the programmer debugging the code, not the office worker staring at the screen in confusion. They knew how the machine worked, and in the absence of anyone else, that knowledge became the only qualification that mattered for the design, for the direction, for the definition of what “useful” even meant. When the role we now call product manager began to emerge in the late 1980s, it was engineers who created it and filled it, because no one else was in the room. “Abort, Retry, Fail?” — the question DOS asked the user, written from the machine’s point of view. The problem was never competence. It was perspective. A programmer is trained to think in terms of function - every state the system can enter, every input it might receive, every branch the code can take. That training instills a specific instinct: when you encounter an edge case, some rare