So many great ideas in the transcript of Ethan Zuckerman's CHI 2011 keynote Desperately Seeking Serendipity:

Online spaces are often so anxious to show me how my friends are using a space that they obscure how other audiences are using it. In the run up to revolutions in Tunisia and Egypt, an enormous amount of reporting (and a not-insignificant amount of organizing) took place on Facebook. If you didn’t have friends in those countries, and specifically in those movements, that activity was entirely invisible. It’s possible to find out what’s popular on Facebook to an audience broader than that of your friends. The Pages directory shows stars, bands and brands with audiences in the hundreds of thousands and millions – strolling through it is a pretty fascinating tour of what’s popular in the Philippines, Colombia and Nigeria, as well as in the US or Canada. Facebook has the data on the desire lines, but they bury it deep within a site rather than bringing it front and center. Twitter’s Trending Topics in an example of making these desire lines visible – we may not know what “Cala Boca Galvao” means when it shows up as a trending topic, or care that #welovebieber, but at least we get indications of what matters to those outside of our list of friends.

Whether we click on an unfamiliar Twitter tag or explore someone else’s annotations of a city map, we’re choosing to stray from our ordinary path. Cities offer multiple ways to wander, as well as a philosophical stance – the flâneur – that prizes wandering as strategy for encountering the city. I think two particular forms of structured wandering have strong potential to be useful in wandering through online spaces.

A few weeks ago, I met an old friend for lunch in New York City. In the twenty years since we’d last met, he’d become a leading figure in the US Communist Party (an organization that, I confess, I thought had disappeared sometime in the late 1960s). As we walked from a restaurant to his office, across from the legendary Chelsea Hotel, he pointed to otherwise unremarkable office and apartment buildings and told me stories about the unions that had built them, the tenants’ rights struggles that had unfolded, the famous Communists, Socialists and labor activists who’d slept, worked and partied under each roof. Our twenty block walk became a curated tour of the city, an idiosyncratic map that caused me to look closely at buildings that would otherwise have been background noise. I begged him to turn his tour of the city into an annotated map, a podcast walking tour, anything that would allow a broader audience to look at the city through his lens, and I hope he will.

One of the reasons curation is such a helpful strategy for wandering is that it reveals community maxima. It can be helpful to know that Times Square is the most popular tourist destination in New York if only so we can avoid it. But knowing where Haitian taxi cab drivers go for goat soup is often useful data on where the best Haitian food is to be found. Don’t know if you like Haitian food? Try a couple of the local maxima – the most important places to the Haitian community – and you’ll be able to discern the answer to that question pretty quickly. It’s unlikely you dislike the food because it’s badly made, as it’s the favorite destination for that community – it’s more likely that you simply don’t like goat soup. (Oh well, more for me.) If you want to explore beyond the places your friends think are the most enjoyable, or those the general public thinks are enjoyable, you need to seek out curators who are sufficiently far from you in cultural terms and who’ve annotated their cities in their own ways.

Another way to wander in a city is to treat it as a game board. I’m less likely to explore Vancouver by following a curated map than I am by searching for geocaches. Within five kilometers of this conference center, there are 140 packages hidden somewhere in plain sight, each containing a logbook to sign and, possibly, mementos to trade with fellow players. As a geocacher, it’s something of a moral imperative to find as many of those caches as time allows during your visit to an unfamiliar city. In the process, you’re likely to stray far from the established tourist sites of the city, if only because it’s hard to hide caches in such busy places. Instead, you’ll end up in forgotten corners, and often in places where the person who placed the cache wanted you to see something unexpected, historic or beautiful. Geocaching is its own peculiar form of community annotation, where the immediate goal is leaving your signature on