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.
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.
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.

Trump Administration Could Effectively End Housing Voucher Program
Federal officials are eyeing major cuts to the Section 8 program that helps millions of low-income households pay rent.

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

Ken Jennings Launches Transit Web Series
The Jeopardy champ wants you to ride public transit.

Crime Continues to Drop on Philly, San Francisco Transit Systems
SEPTA and BART both saw significant declines in violent crime in the first quarter of 2025.

How South LA Green Spaces Power Community Health and Hope
Green spaces like South L.A. Wetlands Park are helping South Los Angeles residents promote healthy lifestyles, build community, and advocate for improvements that reflect local needs in historically underserved neighborhoods.

Sacramento Plans ‘Quick-Build’ Road Safety Projects
The city wants to accelerate small-scale safety improvements that use low-cost equipment to make an impact at dangerous intersections.
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.
Heyer Gruel & Associates PA
Ada County Highway District
Institute for Housing and Urban Development Studies (IHS)
City of Grandview
Harvard GSD Executive Education
Toledo-Lucas County Plan Commissions
Salt Lake City
NYU Wagner Graduate School of Public Service
