Up in the Air: Meet the Man Who Flies Around the World for Free
One hour in, and the three are swapping stories about the time they met the teenage Schlappig at a Hobby party he organized in Sausalito, California. The woman at the table is a corporate lawyer from New York, one of the Hobby’s few females. “I met him, and I was like, ‘Oh, my God,’ ” she recalls. ” ‘This kid is, like, in high school.’ ” Each person at the table has concocted a story for their co-workers or friends about where they disappear to on weekends. But this evening, they’ve found one another in the Hong Kong night. Schlappig spills champagne on himself as he raises his glass for a toast: “So much for lonely, right?”
The next morning, Schlappig is fighting off a hangover as he trudges through Hong Kong International for a flight to Jakarta. He sighs. “I don’t really physically associate anything with being home,” he says, “but this is about as close as it gets.” Bag in tow, he pauses to gaze at the sprawling indoor pavilion. “The Hong Kong airport, the Virgin Atlantic Clubhouse at JFK — I do feel at home there,” he muses. “It’s weird.” Soon, it will be a year since he gave up his apartment in Seattle. He ponders the thought with a glass of white wine somewhere over the Indian Ocean, but for the first time he betrays a note of sadness in his blank smile. “Absolutely, it’s isolating,” he admits. “There are nights where it’s 3 a.m. in Guangzhou, China, and you’re like, ‘Oh, I could actually be in L.A. having fun with friends.’ And there’s nothing to do here.”
Or anywhere: His trip reports betray a theme, in photo after photo entirely devoid of human companionship: empty lounges, first-class menus, embroidered satin pillows — inanimate totems of a five-star existence. On our next flight, a seven-hour run from Jakarta International to Tokyo, Schlappig tries to get himself motivated about the champagne selection, holding forth on the best meal pairings with a $200 bottle of Krug. But there are no fans waiting to surprise him here. An elderly Japanese couple sleep in the corner. Otherwise, the cabin is deserted. Many air carriers long ago made the judgment to let first-class suites go unfilled, at the risk of tainting the marketable aura of exclusivity.
“I do what I love,” Schlappig whispers, perhaps more to himself, trying not to wake the couple. “You have to understand: This has always been my passion.” His words trail off, and he closes his eyes. “Being in your twenties is hard — being a gay guy in your twenties is even harder,” says Nick Dierman, a close friend of Schlappig and a fellow Hobbyist. “Life’s a challenge. I think this is his way of escaping it.” Some of his friends have floated the idea that Ben should become a lawyer. “Why do that?” he asks, more than slightly annoyed. “Why would I want to sit in an office all day when I can just fly around the world?”
By the time the plane touches down in Tokyo, Schlappig has been in seven countries in seven days. He scoops his things and drifts wordlessly to the exit. It’s still dark outside at Tokyo Narita Airport, and at this hour the palace-size structure is nearly empty. A woman sleeps at a McDonald’s table, head back and mouth open, the faint echoes of a vacuum cleaner whirring in some far-off corridor.