In July, I found myself knocking on doors at dusk in a strange neighborhood. I was over a thousand miles from home on the first night of a hitchhiking trip from Denver, Colorado, to Portland, Oregon, and I was going porch to porch to ask if I could pitch my tent in someone's backyard.

Two neighborhood watch signs threatened that "neighbors have been trained to report suspicious activity" to law enforcement. Evidently, it helps to be white and outfitted like an adventurer. After just one refusal, a retired couple welcomed me onto their back porch where we ate blueberries and talked about Yellowstone National Park and forest fires and the natural gas industry.

You might think that hitchhiking isn't possible anymore. So does everyone who picks me up: single mothers with babies in car seats, baby boomers with tramping stories to dwarf my own, high school students two weeks into a driver's license. In America, generosity is our personal secret, repressed by a lifetime of learning to distrust people. "You're not crazy, are you?" one woman asked before driving me into Yellowstone National Park. "Are you?" I replied. When I set off on this trip, I was partially chasing a thrill I'd read about in the writings of Jack Kerouac, among other Beat generation writers, but I'm not going to start preaching the gospel of hitchhiking as they did. I'm aware that the 1950s freewheeling Beats have been discredited as the sons of privilege living out an apolitical fantasy of adventure, slumming with black and immigrant communities and then going home to their middle-class parents to write about it. My situation isn't much different. I have a college degree, parents willing to foot a bill or two, and when I'm trekking up to your house, I don't trip any alarms of racial prejudice.

But, like the Beats, I'm worried that to be "free" in America is at risk of becoming meaningless. I'm not just talking about the NSA converting our private lives to data or the prison system absorbing a shocking percentage of our population. I'm talking about the fact that our choices are increasingly limited to just two: to exploit or be exploited.

When I'm not traveling, I work food service jobs in Chicago, which, along with food stamps, helps me support my decadent hobby of freelance journalism. Sure, I could probably land some office job, working for the handful of people who own everything. But I'd rather not. To some, I might seem the poster boy for American freedom, making just enough money to write and travel and seek my fortune. But once the hope for eventual stability is taken out of this formula, which is the reality for more and more Americans, all that's left is the striving. And that doesn't look good for our brand of freedom. Too often our lives are at the mercy of someone else's interests. A guy who took me from Douglas to Casper, Wyoming opened up about an awfully familiar dissonance in his life. He was around my age, two years of community college behind him, and working for one of the few employers in the desert: the natural gas industry. The problem was, he confided, "I know all about Gasland," the 2010 documentary that helped turn public sentiment against the environmentally destructive gas extraction process known as fracking, now his livelihood. His defense was that "it pays the bills", perhaps the closest thing my generation has to a motto.

I got a ride from a woman struggling with drug addiction, unable to support either her aging father or newborn grandson. I rode across Oregon in a big rig with an ex-cowboy who saw the ranching business automate and get taken over by giant farms, and who subsequently turned to truck driving, hauling freight well into retirement age. Sure, I encountered plenty of uplifting stories as well, sometimes from these same people. And my own experience of thumbing across the west approached, at times, true liberty. But I was surrounded by dissatisfaction and striving – a predicament I felt I was only temporarily escaping. In this tenor, the refrain "at least I know I'm free" sounds less like a line from a prideful anthem than from a sobering prayer. If I could paint the country in one broad stroke, I would say it's a place where one concept of freedom – used to lobby for private interests and free markets – is at odds with another kind: the ability to lead a life you enjoy. Fewer and fewer seem privileged with this second kind. Not Trayvon Martin, who was a victim of a certain kind of racism which had, as its root, private property anxiety. Not the natural gas employee who has consigned himself to a life of doing something that he feels ought not to be done. Even I – who have managed to escape from time to time – always find, upon return, a cordial invitation to fall in line.