For several years, beginning when I was six or seven, I played a hobo for Halloween. It was easy enough to put together. Oversize boots, a moth-eaten tweed jacket, and my dad’s busted felt hunting hat, which smelled of deer lure; finish it up with a beard scuffed on with a charcoal briquette, a handkerchief bindle tied to a hockey stick, an old empty bottle. 

I imagined a hobo’s life would be a fine thing. I would sleep in haystacks and do exactly what I wanted all the time. Since then, I’ve had occasional fantasies of dropping out, and have even made some brief furtive bids at secession: a stint as a squatter in a crumbling South Bronx building, a stolen ride through Canada on a freight train. 

A handful of times I got myself arrested, the charges ranging from trespassing to disorderly conduct to minor drug possession. But I wasn’t a very good criminal, or nomad, and invariably I would return to the comforting banalities of ordinary life. 

I never disliked civilization intensely enough to endure the hardships of abandoning it, but periodically I would tire of routine, of feeling “cramped up and sivilized,” as Huck Finn put it, and I would light out for another diversion in the Territory. 

It was on one such outing, a hitchhike up the West Coast in the summer of 1999, that I met Matt Bullard in a palm-fringed city park in Arcata, California. A dumpster-diving, train-hopping, animal-rights-crusading anarchist and tramp, with little money and less of a home, Matt was almost exactly my age, and from that first time we talked I admired his raconteurial zest and scammer’s panache. 

He considered shoplifting a political act and dumpstering a civil right. As we sat on a park bench in the sunshine, Matt reached into his backpack and pulled out what he called a “magic dollar,” an ordinary bill save for its twelve-inch tail of cellophane packing tape. 

He would dip it into a vending machine, select the cheapest item available, collect his purchase and change, and pull his dollar back out by the tail. An unguarded machine could be relieved of all its coins and every last one of its snacks in the space of an hour. 

It was a very impressive trick. Matt was convinced that there was something deeply wrong with most Americans: they were bored and unfulfilled, their freedom relinquished for the security of a steady paycheck and a ninety-minute commute, their imagination anesthetized by TV addiction and celebrity worship. 

He had decided to organize his life against this fate. He utterly refused to serve; he lived exactly as he desired. Matt’s was the kind of amoral genius that I had always longed to possess. He not only had quit society altogether but was gaming it for all it was worth, like some dirtbag P. T. Barnum. I, meanwhile, would soon be returning to a temp job in a Manhattan cubicle. 

Matt couldn’t understand why I needed to go back, and I couldn’t really myself, but I went back anyway, tugged by the gravity of expectations. In the ensuing years, I got occasional emails documenting Matt’s drift, describing days on grain cars passing through Minnesota blizzards, nights in palm-thatched squats on Hawaiian islands: dispatches from a realm of total freedom beyond the frontiers of ordinary life. 

Two summers ago, Matt sent an invitation that I could not ignore. He was in Minneapolis, building a homemade raft, and had put out a call for a crew of “boat punks” to help him pilot the vessel the entire length of the Mississippi River, all the way to New Orleans. 

Mississippi Drift, by Matt Power | Harper’s Magazine

For several years, beginning when I was six or seven, I played a hobo for Halloween. It was easy enough to put together. Oversize boots, a moth-eaten tweed jacket, and my dad’s busted felt hunting hat, which smelled of deer lure; finish it up with a beard scuffed on with a charcoal briquette, a handkerchief bindle tied to a hockey stick, an old empty bottle.

I imagined a hobo’s life would be a fine thing. I would sleep in haystacks and do exactly what I wanted all the time. Since then, I’ve had occasional fantasies of dropping out, and have even made some brief furtive bids at secession: a stint as a squatter in a crumbling South Bronx building, a stolen ride through Canada on a freight train.

A handful of times I got myself arrested, the charges ranging from trespassing to disorderly conduct to minor drug possession. But I wasn’t a very good criminal, or nomad, and invariably I would return to the comforting banalities of ordinary life.

I never disliked civilization intensely enough to endure the hardships of abandoning it, but periodically I would tire of routine, of feeling “cramped up and sivilized,” as Huck Finn put it, and I would light out for another diversion in the Territory.

It was on one such outing, a hitchhike up the West Coast in the summer of 1999, that I met Matt Bullard in a palm-fringed city park in Arcata, California. A dumpster-diving, train-hopping, animal-rights-crusading anarchist and tramp, with little money and less of a home, Matt was almost exactly my age, and from that first time we talked I admired his raconteurial zest and scammer’s panache.

He considered shoplifting a political act and dumpstering a civil right. As we sat on a park bench in the sunshine, Matt reached into his backpack and pulled out what he called a “magic dollar,” an ordinary bill save for its twelve-inch tail of cellophane packing tape.

He would dip it into a vending machine, select the cheapest item available, collect his purchase and change, and pull his dollar back out by the tail. An unguarded machine could be relieved of all its coins and every last one of its snacks in the space of an hour.

It was a very impressive trick. Matt was convinced that there was something deeply wrong with most Americans: they were bored and unfulfilled, their freedom relinquished for the security of a steady paycheck and a ninety-minute commute, their imagination anesthetized by TV addiction and celebrity worship.

He had decided to organize his life against this fate. He utterly refused to serve; he lived exactly as he desired. Matt’s was the kind of amoral genius that I had always longed to possess. He not only had quit society altogether but was gaming it for all it was worth, like some dirtbag P. T. Barnum. I, meanwhile, would soon be returning to a temp job in a Manhattan cubicle.

Matt couldn’t understand why I needed to go back, and I couldn’t really myself, but I went back anyway, tugged by the gravity of expectations. In the ensuing years, I got occasional emails documenting Matt’s drift, describing days on grain cars passing through Minnesota blizzards, nights in palm-thatched squats on Hawaiian islands: dispatches from a realm of total freedom beyond the frontiers of ordinary life.

Two summers ago, Matt sent an invitation that I could not ignore. He was in Minneapolis, building a homemade raft, and had put out a call for a crew of “boat punks” to help him pilot the vessel the entire length of the Mississippi River, all the way to New Orleans.

Mississippi Drift, by Matt Power | Harper’s Magazine