Photo credit: Erick Gibson

Headlights from the four-wheel-drive truck shine several yards in front of us, illuminating the emptiness there. The high beams are probably visible for miles on this remote stretch of Colorado highway, and though the brightness shatters the perfectly still, pre-dawn darkness, I’m having trouble focusing on the frosted plains outside. I clutch the handlebar above my head as we bounce, mile after mile over rumbling dirt roads, a parade of snowflakes and raindrops coating the windshield the entire way.

The clock on the dashboard reads 6:46, an hour I am not entirely unfamiliar with thanks to early-morning shifts as a truck stop waiter. Still, Friday is my morning off and I’m not spending it in the typical way, asleep beneath a heap of sheets and heavy blankets.

To my left, separated by just an armrest, is a complete stranger. I’ll call him Charles, but he could go by any generically American name, like Jim or Tom or Sam. He’s the kind of guy you might see tailgating with a beer or flipping burgers before Fourth of July fireworks. Despite a light mahogany goatee, he doesn’t look a day over 25. But I have to think he’s at least in his early 40s. He says he has a wife and a kid, and is a college professor with a Ph.D. in mathematics. People generally don’t make up Ph.D.s in mathematics, so I decide to take his word for it.

In the back seat, an arm’s-length away, rests a 12-gauge shotgun. And that’s what has me worried. Charles is taking me to hunt pheasants, but I could just as easily be his prey. He wouldn’t have to look far for a remote field to drop my body in before returning to his warm, suburban home in Denver. But that’s the chance you take when you’ve chosen to live your life as I have—which is to say, entirely on Craigslist.

Back to the beginning

I should explain that I don’t know the first thing about hunting. In fact, I don’t know the first thing about most things.

In the spring of 2009 I graduated with a degree in public communication from The American University in Washington, D.C., and was tossed into the proverbial Real World. My peers and I left a comparative life of leisure—days often beginning at 11 a.m. for noon classes, with only the occasional midterm exam or final paper to trouble us. Our new life’s reality was a not-so-welcoming economy, optimistically labeled the Great Recession. I wondered: Is it too late to pick another major?

Some of my fellow graduates did just that. Facebook networks were amended to reflect plans of law school, post-baccalaureate programs and even boat-building school in New England. Others signed up for Teach for America or AmeriCorps.

The rest of us spent the summer months applying for jobs (only a fortunate few found full employment before our final semester’s books closed), with me tailoring cover letters for any journalism job I could find in this country, and one in Japan. I scheduled coffee dates with my former internship bosses at USA Today, CBS Evening News and The Washington Post. And I scheduled coffee dates with their connections after that. Dead ends. All of them.

Over four months, I submitted more than 180 applications to news organizations in 35 cities. Cops and courts reporter in Lawrence, Kan.? Yes, please. Education beat in Shreveport, La.? Absolutely. Slave for The Howard Stern Show? Sign me up. All the while I endured stinging rejection after stinging rejection (“We fell into a candidate with 15 years’ experience who would be perfect for us”).

In September, faced with meager options, I decided to investigate the only thing four years of college seemingly had prepared me for: Craigslist.

Like most college students, I had used Craigslist for finding odd jobs, furniture and apartments when resources were slim. But could Craigslist supply me with even more than that—like an entire way of life?

I would spend nearly a year attempting to find out. I would use Craigslist to find housing and jobs, of course, but also friends, food, entertainment and anything else that occurred to me along the way. I would live in three cities for three months each. I would permit myself one duffle bag, a safety fund for startup costs and emergencies, and my beat-up Toyota Corolla. And I would abide by one rule: I would only interact with people I met through Craigslist.

Along the way I would blog about my journey, mostly as a journal for my parents and friends. But eventually, the site’s readership would grow to 75,000, and I would find myself entertaining and inspiring people who, like me, were trying to tread the precarious waters of the economy.

Fall: Riding in cars with strangers

It’s early September 2009 and I’m standing tensely in front of the Union Square Whole Foods, scanning the tide of people for three hippies and a dog. This is New York City, so of course I’m in everyone’s way. People are walking in and out of the automatic sliding glass doors, rushing past me with heavy bags to the subway or across the busy street. Some step in front of yellow taxis, ignoring the blinking pedestrian signal as it changes from a mere suggestion to a stern warning.

Many are rushing home to a spouse or a significant other. If they’re lucky, their commute won’t involve interaction with any of the city’s abundantly weird people. I, on the other hand, am looking for strangers.

Like the millions of hustling New Yorkers who deploy human avoidance techniques—earbuds, cell phone conversations, books, newspapers—I am not entirely comfortable meeting complete strangers. I had better get used to it, though. In a few minutes, my life—and soon thereafter, my car—will be filled with alien individuals. The Craigslist journey begins tonight.

To finance my travels to San Francisco—my first city, chosen because it’s the birthplace of Craigslist—I have looked to the site’s Rideshare section. A future companion will describe Rideshare as “digital hitchhiking.” Instead of holding a cardboard sign with a stiff thumb to the wind, users list desired locations on a message board with headlines like: “Need Ride to Atlanta,” or “Ride Offered: D.C. to Houston.”

I posted my own ride in three major cities along the East Coast, offering my car’s empty seats to anyone traveling to California and capable of splitting gas and driving. New York, as it turns out, has the largest number of people interested in traveling west. And so, stomach churning, I left the comforts of my childhood home in Gaithersburg for the Big Apple.

The Craigslist idea was supposed to be a backup plan, a worst-case scenario, a Push Only in Case of Emergency button. I was supposed to get a job and move on with an ordinary life. By clicking “publish,” I took the first step into an unscripted life, and it didn’t feel so good. I was interviewing possible candidates for a cross-country drive when I should have been buying casual business attire for a real job.

On the Manhattan street corner, I reach my hand into my pocket for my phone. I anxiously check the time and shake my head. My potential Rideshare copilots are 15 minutes late. I scroll through recent phone calls and redial a number I haven’t bothered to store in my phone’s address book. No one answers.

I pace for a minute, fearing I’m getting ditched. These people aren’t even my first choice. But as I learn over time, Craigslist has an abundantly flaky user base. Even the person who was intensely interested in the $10 wine rack you posted under Furniture for Sale sometimes turns into a no-show.

I dial again. This time a guy with a scratchy voice answers. “Fifteen minutes,” he assures me. I go back to pacing.

After seemingly half an hour, they arrive and we quickly decide to meet up the next morning. One sleepless night later, I’m off, just like that.

Jon, Julie and Hannah—my copilots on the ride west—are people I never would have talked to before this. If I were sitting next to them at a bar, or on a train, or even in jail, I would have avoided eye contact if I weren’t yielding to the impulse to stare.

Their haircuts are like something out of Edward Scissorhands, streaked bleached blond with turquoise highlights. They wear bull-style nose rings, have what appear to be amateur tattoos and sport acid rocker ripped jeans. Everything about them would send up a red flag to anyone who has ever received a J. Crew catalogue in the mail.

Yet as we drive west on the Ohio Turnpike, I learn to look past their punk armor. Jon, the most talkative of the three, is traveling to Northern California to work the marijuana harvest. He wants to earn enough to buy a van for his band to take on tour. The girls are quieter, and I am surprised to learn all three attended community college before they left New England for a tangential lifestyle.

They tell me that, at night, they sleep in the woods outside truck stops whenever they don’t have a place to stay. And sometimes they jump into empty boxcars to travel thousands of miles, destination unknown. This landed Jon in jail one time. When his cellmates found out he’d been locked up for hopping a train, the entire jail started calling him “Choo-Choo.”

He and his hobo companions are enjoying life for the ride. Coming from a world where declaring a major and charting a career path are viewed as the only path to success, I find myself hoping I can someday escape such a restricting mentality and achieve their level of emotional freedom.

Jon’s stories about traveling in the underbelly of a freight train or hitchhiking make the stench of caked sweat and patchouli oil bearable. Unfortunately my companions are unable to contribute much to my gas fund, and so I leave them in Cleveland, and pick up another Rideshare the following morning. I’m confident they’ll find their way west just fine.