The Connected City (and the One That Forgot How)

Two walks—one through Valencia’s living fabric, one across San Francisco’s dead spaces.

After the 1906 earthquake, San Francisco was rebranded as The City That Knows How—a proud nod to its ability to rebuild fast.

It’s interesting to note that the moniker was popularized by figures such as President William H. Taft in the aftermath of the carnage. This lies in stark contrast to the pathetic nature of what the current president says when disaster strikes the state.

Anyhow—

The name stuck. And so did the attitude.

For the next century, San Francisco prided itself on being the city that figures things out first. It was the hub of the Bay Area’s tech incubator, the place where Steve Jobs always came up with the next big thing (sorry, Trump lapdog, Tim Cook!), and where Google was born. Today, however, AI rules the relatively uninspiring scene in Hayes Valley—a place we’ll return to later.

But walk through almost any part of San Francisco’s 49 square miles, and—for as beautiful as it remains by American standards—it’s clear The City forgot the one thing it used to know how to do: connect.

San Francisco made terrible decisions in the decades following the quake and the war—choices made long before the iPhone and music streaming. Choices it has had decades to rectify. But San Francisco continues to fail miserably to right its urban planning wrongs.

In this first edition of How It Works (and Why It Doesn’t), I’m walking two routes: one across San Francisco, one through Valencia, Spain.

Two cities with civic centers, markets, and old bones.

One still hums. The other limps.

It’s not a beauty contest. It’s a field test in what happens when one culture keeps designing for people and the other lacks foresight, courage, and sociopolitical will.

Let’s go deep and dissect what’s wrong with San Francisco and what’s right with Valencia—not a rant, but reality rooted in history, facts, and objectivity.

This isn’t more of the same. We’re going under the hood—into civic center planning, freeway politics, and the half-fixes that defined modern San Francisco.

Along the way, we’ll see how Valencia built something better—not perfect, but coherent. Proof that cities can still function when design and daily life work in the same direction.

→ The full walk-through and analysis are below for paid subscribers.

If you want thoughtful, ad-free writing that digs into how cities and other systems really work—and why most don’t—become a paid subscriber. $5/month or $50/year (€5/month or €43/year) helps keep this work independent.

Next week: we’ll leave the streets for the studio—to see how one of the world’s most disciplined systems still works when nothing else does.