As I’d mentioned previously, I’m going to be curating a showcase of urbanist iPhone apps at next month’s inaugural FutureEverything festival in Manchester, as part of the Serendipity City Challenge. I figured I’d take the opportunity to work out just what I thought these words taken together might mean, and more specifically how my feelings have changed since I first gave the topic any consideration back in 2003.

Serendipity, of course, doesn’t simply mean “surprise.” Strictly speaking, the word means accidentally discovering something wonderful in the course of a search for something unrelated. The genuine occurrence of serendipity necessarily implies a very powerful order of richness and texture in the world and, to my mind anyway, when you experience it in cities it’s a clear indicator of a healthily functioning urban ecosystem.

Given that the essence of serendipity is its unexpectedness, though, I tend to be wary of products and services that promise to enhance or “accelerate” it. An artificially accelerated serendipity strikes me as leaving precious little room for the real thing to emerge, and us with a set of instincts so attentuated we may not recognize it when we do encounter it.

Accordingly, in the selection of applications I made for FutureEverything, I allowed myself the leeway of a rather loose interpretation. I looked for applications that offered residents and other users of the city instant reads on the state of things, allowing them to change their behavior in response to evolving conditions or to take advantage of unexpected juxtapositions, however momentary.

It’s this ability to pivot on the moment’s demands that strikes me as so essential to the development of urban savoir faire. The nature of cities is such that life in them exposes each of us to the greatest possible variety of conflicts, difficulties, affronts and challenges, even simply desires that are in tension with one another. Learning to deal with these tensions, to negotiate them with aplomb and assurance, is something that generally takes years of experience with a given place. (Indeed, for English-speakers, this understanding of sophistication is encoded in our very language: that’s what it means, after all, to be “urbane.”)

This strikes me as a process which actually can be usefully accelerated by mobile applications and services, as opposed to trying to pin down something as aleatory as serendipity in its truest form. In order to succeed at this, developers will need to help their users actively reconceive of unplanned, emergent circumstances not so much as disruptions in orderly flow and more as opportunities, even potential “nodal points” in their lives.

The lightness and openness I’m looking for in the next generation of mobile services recall an older sense of the fertile unpredictability urban life might entail. This is André Breton, in 1924: “The street I believed was capable of causing surprising turning-points in my life; the street, with its restlessness and its glances, was my true element: there, as in no other place, I received the winds of eventuality.”

To my mind, this is just why we celebrate the street in the humanist-urbanist tradition. Canonically, it functions as mixing-chamber, randomizer, instigator of situations par excellence. I wonder, though, if this can fairly be said to be the case any longer.

If I’m to be honest, it’s only rarely that I experience that kind of charged moment on the street anymore, or in public space more generally. Mostly, I’m head-down and on my way somewhere — and at that, one of a very few consistent places — and if I can judge fairly by their outer demeanor, so are most of the people around me who might have furnished a great measure of the potential “turning-points.”

By contrast, it’s fair to say that something like this happens to me all the time when I’m online: I’ll follow a series of links and wind up somewhere completely wonderful and, equally, unexpected, or get sent a link to some article, image or video that takes me on a similar journey. When the “winds of eventuality” find me these days, I’m generally sitting in front of my laptop.

One of these days, somebody clever is going to figure out how to use mobile services to bring this effortlessly connectionist logic back to street life. With any luck, they turn out to be a way back to the bracing air of possibility the simple act of being on a great metropolitan sidewalk once entrained.

In fact, if done with any verve to speak of, I can see such services giving rise to the moments of heightened awareness and potential I associate with Situationist rhetoric, those precious intervals during which some fortuitous alignment of people, place and circumstance reminds you what life is for and why it’s worth the effort. (For those of us who savor such ironies, it would be particularly delicious if the final triumph and apotheosis of the flaky, incoherent Parisian left of the Sixties was delivered on the shoulders of systems like GPS and the Internet, originally devised, designed and deployed by the military-industrial apparatus for its own ends.)

And that, in turn, finally meets my own personal definition of “accidentally discovering something wonderful in the course of a search for something unrelated.” The technologies of just such a networked urbanism are here, are available, are in our hands — are, in fact, just about begging us to take them up and make use of them in our cities. Who wants to go first?