On a Friday morning I am biking across the Williamsburg Bridge, which links Brooklyn with Manhattan's Lower East Side. I am alone, hundreds of feet above the East River on a deserted promenade, and I think about stories of muggers who clothesline unsuspecting cyclists—on this very bridge. I imagine myself racing along when my bike suddenly stops dead and I catapult over the handlebars and land on the pavement 10 feet in front of my downed cycle. I look back and see a wire, all but invisible, stretched taut two feet above the ground. I look ahead and see four laughing gang youths step out from the bridge girders. They kick me and take my bike, wallet and watch....
I'm halfway across the bridge now and ahead of me is Manhattan, shimmering in spring sunshine. I scan the promenade for hidden dangers. There are no wires stretched taut. In my backpack are 18 want ads from The Village Voice, all along these lines:
UP TO $600 A WEEK
NEED BIKE, BAG, LOCK.
Like my unemployed neighbors—other freelance writers, painters, actors, musicians and dancers who live in the ramshackle lofts of Williamsburg—I need occasional work. "Messengering," as they call it on the street, has replaced cab driving as the hip straight job of the '80s—a way to stay fit while earning money to support your true calling.
Off the bridge, I hesitate at a stop sign and I stare at the lanes of fast, heavy traffic, pondering the physics of a collision between a bus and a bicycle. I see a middle-aged woman in a business suit pedaling casually along the side of the street. I take a deep breath and fall in behind her.
The dispatcher at the nearest service, All Time Courier Systems, asks if I have any experience.
"No, but I used to race mountain bicycles out West," I say.
"Then you ought to be able to handle Fifth Avenue," he replies. "Start fresh Monday."
Monday is cold and cloudy. I buy a rain suit at a used-clothing store. At All Time I sign a contract saying I won't sue the service no matter what happens and that I will make 60% of the price of each run, which varies according to distance.
"Up for a long run?" the dispatcher asks.
It is raining hard, and in the doorway I open the rain-suit package only to discover the pants are missing. Swearing softly, I figure the distance of my two pickups. The first pickup is 54 blocks north on East 53rd Street. I'll drop that off farther uptown on West 110th Street, make the second pickup on West 120th and then drop that off on West 23rd—about 11 miles altogether.
"New here?" asks a skinhead with a British accent who comes up behind me. He is carrying a "fix," which is the ultimate messenger machine: a track bike with a single fixed gear that will not coast but requires constant pedaling and has no brakes. "Don't worry, mate. You'll catch on. I started with a three-speed. Name's Mick."
Mick shows me a shortcut, but by the time I reach 53rd I'm soaked from the waist down. Twenty minutes later I am shivering on a doorstep on 110th Street. No one answers the buzzer. I scream at the closed door. Then I leave to make the other pickup at 120th, splash downtown through the downpour to the drop-off and return to All Time. I have logged a single run in two hours.
"Why didn't you call from uptown?" the dispatcher asks, shaking his head at my stupidity. "Always call soon as there's a problem. The guy at 110th phoned to tell us he'd be out for 15 minutes. Someone's got to go back up there."
"On my way," I say, ashamed. In the afternoon, I search for an address for an hour in the financial district and lose another 30 minutes wandering around the World Trade Center. Every time I call, the dispatcher says, "Call back in 10." At 5 p.m., back at All Time, I run into Mick, the skinhead.
"I only did 17 today," he says. "How many did you get?"
"Five," I mumble. My neck aches from a thousand quick glances over my shoulders at traffic.
On the ride home, I come to the conclusion that the dispatcher rewards the quick and punishes the slow. He can starve you or he can make you rich. The best of Manhattan's messengers average $100 a day, delivering 25 runs. In my first eight hours I earn $25.
But I get better as the days pass. Two weeks later, cranking down Broadway at 30 mph, standing on the pedals and pulling hard on the bars, I draft off a limousine. A rider on a fix rockets past me and I follow him closely through a red light until he shoots the narrows between two moving buses with an inch of clearance on each side of his handlebars. Even after two weeks, I won't shoot the narrows without at least a foot of clearance. In two weeks of pedaling around Manhattan I've learned to ride out in the middle lanes where you're safe from doors flying open and cars pulling in and out of the flow. I'm up to 15 runs, $50 a day—about average for the city's 4,000 messengers. I'm no longer scared on the street. I juggle addresses, daydream and automatically scout ahead for danger.
After three weeks, I quit All Time. Three weeks, I'm told, is too little time to turn into a fiercely competitive courier. They say that takes at least six months. By then you're fast, a master of survival techniques. Ennui has set in so you race even faster along the streets to fight off boredom and to fill up your bank account.
Heading home at 10 that last night, I am trying to decide whether to risk the Williamsburg Bridge, a route I have never dared take at night but one that would get me home in 10 minutes, or go an hour out of the way over the Brooklyn Bridge, which is perfectly safe. A rider with a messenger's bag slung over one shoulder stops beside me as I hesitate under a streetlight below the bridge.
"Ever ridden the Williamsburg Bridge at night?" I ask.
"Yeah. Used to live over there. Always fantasized about being clotheslined."
"So the bridge isn't safe?"
"The bridge is safe. You might run into some teenage crackheads," he says, laughing. "Just hang your U-lock on your handlebars where you can grab it. It's a great weapon."
Carrying my bike up dark steps onto the promenade, I feel my heart pounding, but I can see no one for 200 yards. Beyond that shadows obscure the road.
"Go, baby, go!" shouts the messenger from under the streetlight.
Intoxicated by adrenaline, bent over in an aerodynamic tuck, I climb from the Manhattan side to the bridge's arch. Then I shoot down through the dark, taking the hill much faster than ever in daylight. And I am home in 10 minutes.
Carter Coleman's book on extreme sports, "Rad Lands," will be published next year.