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.

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The 75-year-old Ayatollah Ruhollah Khomeini had been exiled from Iran for 14 years. His relentless critiques of Shah Reza Pahlavi, Iran’s autocratic leader, had led to the ayatollah’s expulsion, but had not silenced him. In 1977 he was living in neighboring Iraq, where he found a new way to share his message. Late in the evening, usually around 10, after the masses of pilgrims who’d come to visit the shrine of Imam Ali had left for the day, the ayatollah presented long lectures to anyone who would listen. The speeches were anti-shah diatribes, filled with conspiracy theories that tied the shah’s Westernizing reforms to “the Jews and the Cross-worshipers” who sought to humiliate and subjugate Iran.

A few Iranians—no more than 1,200 a month—were allowed to visit Iraq to worship at the shrine, and a small number of them returned home with an unusual souvenir: a cassette recording of the ayatollah’s sermons. These cassettes were copied and freely distributed in the streets of Tehran and other Iranian cities. Pressured by President Jimmy Carter of the United States to live up to his promises of reform, the shah instructed his secret police, SAVAK, not to seize or destroy copies. The tapes were marked “Sokhanrani Mazhabi”—religious lecture—and sold next to tapes from the popular singers of the day. Parviz Sabeti, head of SAVAK’s “antisubversion” unit estimated that more than 100,000 sermon cassettes were sold in 1978 and that millions of Iranians might have heard Khomeini’s anti-shah invective.

Amir Taheri was editor of the pro-shah newspaper Kahyan when the tapes became popular. Two of his reporters brought him a recording they had bought in the market, and the three listened together. They quickly concluded that the voice on the tape was that of an actor, hired by SAVAK to imitate Khomeini and discredit him. After all, Khomeini was a respected scholar, if a political radical. Why would he stoop to conspiracy theories, telling listeners that the shah had commissioned a painting of the Shia leader Imam Ali with blond hair and blue eyes, signifying the shah’s hopes that American Christians would dominate Iran? If this wasn’t a joke, then it had to be an attempt to frame and discredit the cleric.

A few months later, Iran’s minister of information, Daryoush Homayoun, published an editorial in Ettela’at, the country’s oldest newspaper, titled “Black and Red Imperialism.” A wide-ranging smear of the ayatollah, the article accused Khomeini of colluding with the Soviets (the “red” to conservative Islam’s “black”), of being a British spy, and of homosexuality. But Homayoun had underestimated the popularity of the exiled scholar. On January 9, 1978, 4,000 students took to the streets and demanded retraction of the article. Iran’s powerful army quickly quelled the protest, but killed several students and wounded more in the process.

The death of the students opened a cycle of protest and government overreaction that rapidly destabilized the country. Shia custom requires memorial services, called Arbaeen, 40 days after a death. Protests accompanied the services for the dead students, and the shah’s troops shot more protesters; that provoked more services, more protests, and eventually general strikes. Scholars estimate that as much as 11 percent of Iran’s population participated in these protests, a higher percentage of the population than participated in Russia’s or France’s popular revolutions. By January 1979, it was the shah who had gone into exile, and a triumphant Khomeini returned to Iran, where more than 3 million Iranians took to the streets to welcome him. Four months later, a referendum with wide popular support declared Iran an Islamic republic.

Khomeini’s quick rise surprised the shah’s supporters, who had seen Iran moving away from Islam and toward a secular state, where women had the vote and Iran had strong ties to the West. Khomeini’s subsequent brutal consolidation of power surprised students who had supported him, taking seriously his promises of freedom and anti-imperialist democracy, only to see hundreds of the ayatollah’s political opponents summarily executed. And the exiled Iranian politicians who had flown from Paris to Tehran with Khomeini were certainly surprised when, two years later, many were dead or in exile again.

But perhaps no one was more surprised than Jimmy Carter. On New Year’s Eve 1977, days before students took to the streets of Qom, he had toasted the shah, declaring, “Iran, because of the great leadership of the shah, is an island of stability in a turbulent corner of the world.” Carter’s analysis was echoed by the CIA, which dismissed the protests of 1978 in August of that year, asserting, “Iran is not in a revolutionary or even ‘pre-revolutionary’ situation.”

How did the intelligence service of the world’s most powerful nation misread the Iranian revolution so badly?

In the waning years of the Cold War, the job of America’s intelligence analysts began to shift, becoming vastly more complicated. In earlier decades, analysts had known who the nation’s main adversaries were and what bits of information they needed to acquire: the number of SS-9 missiles Moscow could deploy, for example, or the number of warheads each missile could carry. They focused on discovering secrets, facts that exist but are hidden by one government from another. But by the time the Soviet Union completed its collapse in 1991, as Bruce Berkowitz and Allan Goodman observe in Best Truth: Intelligence in the Information Age, the intelligence community had a new role thrust upon it: the untangling of mysteries.

The computer security expert Susan Landau identifies the 1979 Islamic revolution in Iran as one of the first signs that the intelligence community needed to shift its focus from secrets to mysteries. On its surface, Iran was a strong, stable ally of the United States in a conflict-torn region. The rapid ouster of the shah and the referendum that turned a monarchy into a theocracy under Khomeini left governments around the world shocked and baffled.

The 1979 revolution took intelligence agencies by surprise because it was born in mosques and homes, not in palaces or barracks. Even if the CIA was watching Iran closely, it was paying more attention to troop strength and weaponry than to cassette tapes sold in the marketplace. Analysts missed a subtle change in Iranian society: the nation was becoming more connected, both internally and to the outside world, through the rise of new communications technologies.

In their book analyzing the events of 1979, Small Media, Big Revolution, Annabelle Sreberny and Ali Mohammadi, who both participated in the Iranian revolution, emphasize the role of two types of technology: tools that let people access information from outside Iran, and tools that let people spread and share that information on a local scale. Connections to the outside world (direct-dial long-distance phone lines, cassettes of sermons sent through the mail, broadcasts on the BBC World Service) and tools that amplified those connections (home cassette recorders, photocopying machines) helped build a movement more potent than governments and armies had anticipated.

The ouster of autocrats in Tunisia, Egypt, and Libya in the 2011 Arab Spring protests has reopened a conversation about the role of technology in enabling social change. Did cassette recorders overthrow the shah? No more than Facebook ousted Mubarak. But in both cases, the technological, political, and social fabric shifted, and old ways of anticipating what changes might occur were no longer applied. Looking for secrets—the missing information in systems we understand—we can easily glide past mysteries, events that make sense only when we understand how systems have changed.

As we enter an age of ever-increasing global connection, we are experiencing vast but subtle shifts in how people communicate, organize themselves, and make decisions. We have new opportunities to participate in conversations that are local and global, to argue with, persuade, and be persuaded by people far from our borders. And we have much to argue about, as our economies are increasingly intertwined, and our actions as individuals and nations affect one another’s climate, health, and wealth. And as these connections increase, it should be no surprise that we will also experience a concomitant rise in mystery.

The mysteries brought to the fore in a connected age extend well beyond the realm of political power. Bad subprime loans in the United States trigger the collapse of an investment bank, which tightens interbank lending, pushing Iceland’s heavily leveraged economy into collapse, leaving British consumers infuriated at the disappearance of their high-yield savings accounts at Icelandic banks. A family wedding in Hong Kong leaves the World Health Organization tracing a deadly epidemic from Toronto to Manila, the disease spreading as fast as individuals can travel. Not all mysteries are tragedies. Political revolutions, broadcast live from Tunisia, send students into the street in Gabon to demand lower tuition, and inspire labor activists in Wisconsin to seize the state capital. A Korean pop song mocking the materialism of a neighborhood in Seoul, PSY’s “Gangnam Style,” becomes a global dance hit in an instance of unexpected and convoluted connection.

Uncovering secrets might require counting missile silos in satellite images or debriefing double agents. In order to unwind a banking collapse or combat SARS, we need different skills. Landau suggests that “solving mysteries requires deep, often unconventional thinking, and a full picture of the world around the mystery.”

The popular embrace of the Internet means we have a wealth of new ways to learn what’s going on in other parts of the world. It’s as easy to access the front page of a newspaper from another continent as it is to read one from the next town. In fact, sometimes it’s easier. A free online encyclopedia offers background and context on events that would have been hard to obtain 10 years ago without visiting a good library. Google promises to organize the world’s information and make it universally accessible, and we’ve grown used to asking it and other search engines to discover secrets: just type “How many SS-9 missiles does the USSR have” and hit “I’m feeling lucky.”

These tools help us discover what we want to know, but they’re not very powerful in helping us discover what we might need to know. What we want to know is shaped by what, and who, we think is important. We follow the news in our hometowns more closely than news an ocean away, and the lives of our friends in more detail than those of distant strangers. Our media tools, ranging from our newspapers to our social networks, embody those biases; they help us find what we want, but not always what we need.

What do we need to understand a complex and interconnected world? That’s not just a question for intelligence agents. Epidemiologists and CEOs, environmentalists and bankers, political leaders and activists are all trying to tackle challenges of global scale. We all need ways to access perspectives from other parts of the world, to listen to opinions that diverge from our preconceptions, and to pay attention to the unexpected and unfamiliar.

We move from unearthing secrets to unwinding mysteries not just through the force of will. Our understanding of the world comes to us through the tools we use to learn about the world around us. Some of those tools are hundreds of years old, whereas others were invented in the past decade. And all of them can be changed to help us better understand and explore the world.

We can build new tools that help us understand whose voices we’re hearing and whom we are ignoring. We can make it easier to understand conversations in other languages, and to collaborate with people in other nations. We can take steps toward engineering serendipity, collecting insights that are unexpected and helpful. With a fraction of the brainpower that’s gone into building the Internet as we know it, we can build a network that helps us discover, understand, and embrace a wider world.

We can, and we must, rewire.

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