By now, most of us have grown used to the role social media plays in our lives: we message our friends on Twitter, share photos through Instagram or Facebook, and comment on our friends’ check-ins or look for travel tips on Foursquare. I am as immersed in this as anyone, since social media is a big part of how I do my job. But every now and then, I try to refresh my memory about how disruptive these technologies really are — and one of the most powerful aspects for me is the way that each of them can function as a kind of serendipity engine in our lives, if we want them to. In other words, they can randomize our experiences in ways that were never before possible, as they did for me on some recent trips to New York and San Francisco.

One example: After arriving in New York for a conference and some meetings earlier this year, I decided to go for a stroll through The High Line park on the Lower West Side near the Meatpacking District — a wonderful park that used to be an elevated subway track and is now a huge green space that stretches for about 15 blocks. While I was walking, I decided to check in on Foursquare, since I had never been to the Highline before, and within a minute or two I had a message from someone who saw my check-in on Facebook: they were just a few blocks away and wanted to meet for a cup of coffee.

Randomness can be a very powerful feature

Ironically, this incident took place just hours after I had told someone that I didn’t really use the check-in feature in Foursquare to meet people very much, but mostly used it for tips about restaurants. But after that experience — which resulted in a fascinating discussion with someone I had been trying to meet up with for some time, with no success — I decided to try it more often.

On my next trip to New York, I looked at Foursquare’s stream of friend check-ins to see where some of the people I follow on various services were, and noticed that someone I knew was at a sushi restaurant not far from me. I messaged him on Twitter, but unfortunately he had already left. Since I had an hour or two to kill, however, I checked my stream and saw a photo of Times Square that someone I knew had posted just a few minutes earlier. I messaged her and we wound up meeting for coffee the next day — even though neither of us knew the other was in town until that moment.

On a recent visit to San Francisco for a GigaOM conference, I had a similar experience from the opposite side of the coin: I posted a photo of a street near where I was staying in an AirBnB apartment (another eye-opening experience that I wrote about recently) and within minutes someone had posted a comment saying the street was just a few blocks from where they lived, and offered to buy me a coffee. We had breakfast the next morning at a local cafe, and not only was it a fascinating conversation but we happened to be sitting by the window when the Space Shuttle flew by on its last voyage. Talk about serendipity.

Increasing the likelihood of “bumping into” someone

Not all of my experiences with this kind of random meet-up have been deep or hugely meaningful — in some cases, they have just resulted in someone saying hello, as a New York staffer from a large blog network did on my last trip to the city, when I checked in and posted a photo from Stumptown Coffee Roasters in Chelsea. He introduced himself and said he saw the check-in, and we chatted a bit while we were getting our coffees and then said goodbye. That afternoon, a CEO of a local startup saw that I had checked in nearby, and sent me an email and we wound up meeting for coffee.

Obviously, this kind of chance meeting was possible before social-media tools like Twitter or Instagram or Foursquare came along — you could bump into someone at the store, or on the street, or at the newsstand. But the chance of those things happening is much larger now (or could be, if more users allowed it to happen). Those tools enhance the likelihood that someone who is in your social graph will see your virtual location, and the two of you can connect much more easily through a variety of services as well, so that semi-random meetings become much more appealing.

Not everyone is going to want to throw their calendar out the window or outsource it to Twitter and Foursquare, of course, and in some cases it introduces a lot more randomness than you might want during a short trip to a strange city. I’ve also had lots of emails and direct messages from people I don’t really want to meet with, which is a side effect of the same phenomenon, and I have planned dozens of meetings that never actually occurred. But the vast majority of the ones that did happen were worth it — and that injection of randomness or serendipity is one of the unsung features of social-media tools, at least for me.

Post and thumbnail images courtesy of Flickr users Mark Strozier and Shutterstock/MrJPEG


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