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I decided to cast my net wide, and asked a flight attendant to make an announcement to the entire cabin, requesting that people ring their call bells if they could recommend a hotel for the night. I imagined the plane lighting up like a Christmas tree as, one by one, my fellow travelers suggested their favorite Tokyo lodgings or offered keys to their unused pieds-á-terre.

The flight attendant politely informed me that the other passengers had not signed up to be my personal travel agents. But he offered to make up for it by consulting with the rest of the Tokyo-based crew. Several minutes later, he found me in the darkened cabin and handed me a piece of paper with suggestions, including "Asakusa."

"This is my neighborhood," he said, introducing himself as Yori. "And this," he pointed at a different word, "is a hostel popular with backpackers." I hadn't even arrived in Tokyo and I had already learned two important lessons. First, it's not that scary to ask people for help. Second, I should dress better.

When I asked Barry Glassner, PhD, sociologist and author of The Culture of Fear, why we love guidebooks so much, he hypothesized that it's because relying on experts alleviates our fear of the unknown and makes us feel more in control. It's an approach that makes total sense, except for one thing: It's an ineffective way to plan a fun trip.

The problem with guidebooks has to do with what psychologists call affective forecasting—our ability to predict our emotional (that is, "affective") reaction to a future event. It's a skill at which we're not particularly good. We overestimate how much a positive event will improve our lives; we underestimate our ability to bounce back from hardship. And when it comes to travel, we're likely to be remarkably bad at predicting how much we'll enjoy the very experiences we've so carefully researched. "People have the notion that if they just gather the right information themselves, they'll make a better prediction of their reaction than they would if they tried to replicate the good experiences of others," says Matt Killingsworth, who runs a project out of Harvard called TrackYourHappiness.org. "But we've found the opposite to be true."

The key, Killingsworth insists, is that bit about "replicating the good experiences of others"—instead of basing our decisions on our own research and analysis, we should just ask other people whether they had a good time. He's got ample research to back this up, but I still fall into the large camp of people who find it hard to believe that strangers could be better than a guidebook at predicting what I'll like.

So I was surprised when I emerged from the train station at Asakusa to find that in this case, Killingsworth—or at least the flight attendant—might have been right: The neighborhood was in northeast Tokyo, a subway ride from downtown, and would never have jumped out at me on a map. But it was perfect. Instead of the high-rises and endless brand-name stores that characterize downtown, Asakusa was filled with charismatic pedestrian streets lined with small shops and restaurants, and was home to the Sensoji temple, the oldest in Tokyo. After dropping my bags at the hostel—which was clean, if basic—I asked for a restaurant recommendation in English from a young mother on the street and ended up in a small restaurant that specialized in tempura. Soon I was digging into the waitress's favorite dish: a bowl of fried shrimp on top of rice. It wasn't the best tempura I'd ever had, but I didn't care. Alone in a strange city on my first night in town, I felt inspired by my experiences thus far—and excited about what might happen next.

"Getting up before dawn to watch a tuna auction is not something I normally do"

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