We imagine ourselves to be citizens of the world, but in fact we are drawn to people like us, to familiar experiences, and to information that confirms our biases. This is the phenomenon Ethan Zuckerman, who is my advisor at the MIT Center for Civic Media, calls “imaginary cosmopolitanism.” We could potentially read the daily news from Lagos, Nigeria on our laptop while we’re wearing pajamas. We could follow trending tweets from Turkey. But the imaginary part of the cosmopolitanism is that we don’t.

Can we build technologies to engineer serendipity when it comes to global news? That is the challenge that my colleague Matt Stempeck and I took on when we decided to build a program to help people discover the places they never read about and the cultures they do not inhabit. We might only be able to travel to a certain number of places in our lifetime, but technology can allow us to explore places we might never visit—and understand our own cultures more deeply as a result.

To this end, we created a game called Terra Incognita: 1,000 Cities of the World after the “unknown lands” label that was inscribed on ancient maps. The program incorporates itself into the Google Chrome web browser when you download it. And each time you open a new tab, it creates a kind of “gateway” home page that gives you a map of and links about an international city Americans tend to ignore, or where the mainstream news coverage is oriented to conflict and violence. Sumqayit (Azerbaijan), Ürümqi (China), Aguascalientes (Mexico), and Algiers (Algeria) are a few of the places you might end up exploring.

We try to pick links that introduce people to interesting information—on food, sports, music, and entertainment, for example—that challenges stereotypes. For those who are bold, there’s a red button that says, “Fortune favors the brave,” which takes you to a trending news story about that city.

There’s an element of competition, too. As you read about cities, each one gets logged on the bar at the bottom of your screen. Each time you visit one of these city “gateway” pages, you see the username of the person who has read the most articles about that city. And you don’t have to read about the cities from the application’s interface to play. If you read an article online about Baotou, China, for example, without using Terra Incognita, you still get credit.

In our effort to use technology to introduce people to global news and information that they might otherwise never access, we have hit a few roadblocks. The five travails of engineering serendipity include:

1. There are still lots of Internet blank spots
For example, it turns out to be fairly difficult to find information in English about mid-sized cities in China like Wenzhou, Anshan, or Shijiazhuang. Our team has been working on the problem from multiple angles. We have people out link-hunting for us. We harvest what others in Terra Incognita are reading for recommendations. And we use an algorithm supplied by the link-shortening site bit.ly to get trending news related to particular cities. But, take a look at Oujda, Morocco in our program. Despite taking all the above-mentioned steps, there are still no recommended links for that city.

2. The way this technology “reads” stories is far from perfect
I have spent two years at the Center for Civic Media developing technology to detect from a news story the location of the place the story is about. It’s something that a human reader can get in a snap, but it’s very difficult to program computers to do this. I think our results are really good: Based on analyzing the text, our program can tell us what country a story took place in with about 85 to 90 percent accuracy. But, even when the technology is working as it should, it is not what humans expect. For example, the algorithm kept telling us that xkcd, a web comic by Randall Munroe of Massachusetts, was about Chengdu, China. It turns out that the source code for all xkcd pages mentions China. The geolocation technology then decided the page was about China, and tried to locate it at the capital city—which was incorrectly marked as Chengdu in a spreadsheet.

3. Humans are wicked complex
It is hard to figure out what kind of information about a place will be most interesting to people who might have very little knowledge. What would pique your interest about that mid-sized Chinese city of Shijiazhuang? Would it be a Wikipedia article, a long-form magazine article, a BuzzFeed listicle, or an item from a daily newspaper that connects with your personal interests? Information is hard enough to come by—even when we already know that we want it.

4. Incentivizing wandering over “what you want”
Wandering on the Internet is a concept that sounds romantic until you are actually lost and become terrified, baffled, or bored. This is why wandering needs to be mitigated with a light touch. We must feel safe, and we must be open to, and have time for, new information. This is where entertainment, humor, and games are especially useful. For example, you probably did not set out at the beginning of the day to learn about Ségou, Mali, but perhaps this article about the Malian hip-hop scene can change your plans.

5. You can’t engineer serendipity
This is a conclusion that I have reached after this research. Think about the last time you experienced a moment of serendipity. It is a personal and circumstantial affair that results from a fleeting moment of intersection between you and the universe. So instead of trying to engineer serendipity itself, we can try to engineer the conditions for experiencing serendipity. These include helping people change up their routines, reflect more deeply, make mental space, look for patterns, and seize opportunities. Almost all of these are incompatible with the high-pressure, task-oriented environment that many of us find ourselves in if our work involves the Internet.

Despite these challenges, we are seeing some interesting preliminary results. Over 200 people have downloaded the app. The vast majority of users we surveyed (87.5 percent) say that they have learned about a new place from Terra Incognita, and most of them (63 percent) think that Terra Incognita prompted them to reflect on the geography of the news they read. While we still have more work to do to improve the quality of Terra Incognita’s reading recommendations, there’s something to be said for people ending up in new places online a couple times more often each day. If we can design technologies that don’t just accomplish tasks but actually help us make space and time to experience the world, then we might have a chance at serendipity.

Terra Incognita is available for free download from the Chrome Web Store: http://bit.ly/V4GFjh.