Why Cities Work: Surprise

A few months ago, when I was still taking the bus to work - and walking from San Francisco's Transbay Terminal to my office - my favorite shortcut got strange. And I'm glad it did, because it helped me crystallize one of the necessary qualities for a great city: surprise. I'd taken to shaving a few minutes off the march by cutting down a narrow walkway between two skyscrapers. Tall brick on one side, tall concrete on the other. And at the end: pop. The backend of a simple plaza, bits of crummy retail and a Starbucks guarding the front.

3 minute read

January 21, 2006, 9:51 PM PST

By Anonymous


A few months ago, when I was still taking the bus to work - and walking from San Francisco's Transbay Terminal to my office - my favorite shortcut got strange. And I'm glad it did, because it helped me crystallize one of the necessary qualities for a great city: surprise.



I'd taken to shaving a few minutes off the march by cutting down a narrow walkway between two skyscrapers. Tall brick on one side, tall concrete on the other. And at the end: pop. The backend of a simple plaza, bits of crummy retail and a Starbucks guarding the front.



Then, one morning, my shortcut had art in it. Multicolored, ten-foot-tall sculptures lined the brick wall. Same deal in the plaza, only with stone, a piece that looked like an I-beam twisted into a park bench, even a brushed-steel kinetic thing. The unoccupied bit of street-level retail space had turned into an art gallery specializing in sculpture, and the gallery had populated the plaza with big, public-scale work.SF shortcut art



I've been lucky enough to live in most of the great American cities, and in each I've had occasion to take near-daily walks along the same route. I tend to walk the same way every time not because I'm habitual (though I guess I am about some stuff) but because the walk gives me a chance to see more and more details about the route. Every pass lets me increase the magnification on my observations, in a way.



But what was great about the art in my shortcut was that it surprised me - it was like seeing a whale swim past my microscope's field of view (to torture that magnification metaphor from the last paragraph). It forced me to touch the changing fabric of the city on my harmless way to work, instead of minding my own business. I realized: this is why I love cities, or some cities. You never know what's going to happen when you turn a corner. Yes, sure, sometimes surprise equals inconvenience when it involves the inaccessibility or unavailability of something you were counting on…or worse, when it actually translates into danger.



Not everyone likes facing the requirement of constant adaptation. Those people do not live in cities, or do not like cities, or live in cities that are bad at generating surprise.



So the question is, how can a city foster the qualities of being new and strange?



First of all, it has to happen at the street level. Anything that you have to drive to and find parking for is not going to be surprising (though it might be a lot of fun). I'm pretty sure that surprises happen in the spaces between our scheduled experiences.



So that means, secondly, the street level of the city has to be flexible. It needs spaces in buildings where people sell things, certainly, but also spaces in front of those buildings for things to happen - political demonstrations, chance meetings, farmer's markets.



And thirdly, the city has to create circumstances where surprising things can happen. Annual events are good. Concerts in parks. Festivals. If you add scheduled experiences, more people pass between them, and more surprises happen in the intersticial spaces.



I don't take the bus to work much anymore. For personal reasons I've started driving, which means the most surprising thing that happens to me on the way to work is a variation in traffic over the Bay Bridge, or a song I've forgotten about turning up in my iPod's shuffle.



It kind of sucks.


portrait of professional woman

I love the variety of courses, many practical, and all richly illustrated. They have inspired many ideas that I've applied in practice, and in my own teaching. Mary G., Urban Planner

I love the variety of courses, many practical, and all richly illustrated. They have inspired many ideas that I've applied in practice, and in my own teaching.

Mary G., Urban Planner

Cover CM Credits, Earn Certificates, Push Your Career Forward

Logo for Planetizen Federal Action Tracker with black and white image of U.S. Capitol with water ripple overlay.

Planetizen Federal Action Tracker

A weekly monitor of how Trump’s orders and actions are impacting planners and planning in America.

June 18, 2025 - Diana Ionescu

Two people walking away from camera through pedestrian plaza in street in Richmond, Virginia with purple and white city bus moving in background.

Vehicle-related Deaths Drop 29% in Richmond, VA

The seventh year of the city's Vision Zero strategy also cut the number of people killed in alcohol-related crashes by half.

June 17, 2025 - WRIC

Two small wooden one-story homes in Florida with floodwaters at their doors.

As Trump Phases Out FEMA, Is It Time to Flee the Floodplains?

With less federal funding available for disaster relief efforts, the need to relocate at-risk communities is more urgent than ever.

June 16, 2025 - Governing

Close-up of green and white sign for 1 hour EV charging station outdoors with tall palm trees in background against blue sky.

Judge Reverses Federal Funding Freeze for EV Infrastructure

A federal judge ordered the Trump administration to release funding for the National National Electric Vehicle Infrastructure Program, a $5 billion program aimed at improving charging infrastructure.

15 minutes ago - News From the States

Wide street in Santa Monica, California with cars parked on either side and tall palm trees lining the street on a sunny day.

Santa Monica May Raise Parking Permit Fees

The city says the changes would help better manage curb space and support its sustainability goals.

2 hours ago - Westside Current

Brick building with high-rise under construction with yellow crane in background in downtown Portland, Oregon.

Portland Housing Bond Created Nearly 5,000 Units, But Affordability Remains Out of Reach

Despite better-than-expected results from multiple local housing bonds, housing costs and homelessness remain top of mind for many Oregonians.

4 hours ago - Governing

Urban Design for Planners 1: Software Tools

This six-course series explores essential urban design concepts using open source software and equips planners with the tools they need to participate fully in the urban design process.

Planning for Universal Design

Learn the tools for implementing Universal Design in planning regulations.

Write for Planetizen