Late at night after these uncertain days, many of us are having pandemic-stirred anxiety dreams—endlessly being chased, the foiling of vital tasks, stymied odysseys balancing life or death, falling from high places—while those of us hooked on travel simply pine for unclipped wings instead of falling. Learning that the iconic guitar riff for the Rolling Stones' "Satisfaction" came to Keith Richards in a dream, I've always wondered when a dream would inspire me, until a recent would-be nightmare concluded in triumph.
I dreamt that I was about to give my 150-country travel talk, The Directions to Happiness, in my middle school auditorium before students, teachers, friends and locals in suburban Garden City, NY. Just before going on, my hunt for a restroom spilled into a plagued maze that wound me over rooftops, into tunnels, and through backyards that progressively made me later and later for the gig. Worse, I suddenly realized that I'd forgotten the globe-spanning images that rooted my talk. After finally locating the school, I stood before it, beaten down and dirty, until a revelation sent relief rushing through my veins. I didn't need the images nor any far-reaching globetrotting tales when all I had to do was tell the truth, something I've been doing anyway for the past 10 years (and why I'm able to be in a relationship lasting that long).
In a flash, I morphed the presentation to showcase the life-defining adventures I'd had as a seventh through ninth grader who couldn't rub two nickels together, as that epoch ultimately defined where I was heading long-term. As I strolled toward the auditorium, smiling and armed with a throwback plot, I woke up in my NYC bedroom and beelined for my laptop for a voyage back. Way back.
This dream unveiled that the seeds of my globetrotting career were sprouted and honed by a childhood combo of bold adventure and mild delinquency that overran my every waking moment. All the components of thrill-seeking and bucket listing—the nuts and bolts of travel writing—transpired then. These included urban spelunking, skiing without skis, all-terrain crusading, and freestyle climbing despite Long Island being utterly flat. On any journey tethered to the unknown, the first thing we pack is ourselves.
My first advocate for wandering during elementary school was a golf course in another town I lived in, Hempstead, NY, that taught me to keep one eye on the road and the other on reasons to detour from it. Before I'd turned 10, I was set loose with the skill sets required to hitchhike, sneak out of our house at night without parental detection, sprint away from police cars just to invite a chase, crawl invisibly for blocks through the continuum of hedges separating suburban backyards, scale any building in town, and permanently borrow things from department stores. I soon figured out how to endure and resolve disciplinary interrogations from crabby adults, like the golf course greenskeeper who begrudgingly failed to expose my golf ball reselling scam, or detect my tree house looming in a pine tree hovering over a putting green. Heightened anarchy.
The first indication of a preference for alternative transport was my passion for navigating the entire length of the rusty chain-link fence surrounding the golf course without touching the ground. Mock rock climbing decades before it hit gyms and malls, I clung along the miles-long eight-foot barrier, which required a full day of plotting routes through or around vines, bushes, and honeysuckle blossoms. There were also tree branches that were either overhanging or enmeshed into the fence. Enduring such odysseys, I'd often find myself gripping a listing fence with my back to the ground. Falling and touching the soil once meant total failure—and a return to the starting point.
Bathing in mischief's cologne launched my life on the road. It also put a new spin on getting lost, just for the heck of it. I continue encouraging nearly everyone I meet to follow that unsigned dirt road—metaphorical or actual—to discover their own set of rat-race exit blueprints.
My interest in caving started in seventh grade when various pals and I used the rainwater drainage tunnel system to explore the otherworld beneath the streets of our village. Jim, already keen on infrastructure and now a civil engineer who has rebuilt New York's three airports, long ago invited me to view sumps—gritty rainwater holding basins—as suburban ponds. One such sump, conveniently located behind Jim's house and parallel to our high school's athletic field, made entering the tunnel easy. He connected a BMW car seat to the base of a baby stroller, attached a few truck side-mirrors for style, and we were off. With one of us pushing and the other one seated and holding a flashlight, we explored endless miles of interconnected, convoluted tunnels leading to periodic streetside sewer compartments.
Sometimes losing our way on account of too many bends, compartments, and intersecting routes, we'd eliminate the risk of not finding our way back by exiting skyward through various manhole covers. This was also a possibility when our flashlight batteries died, and we were rendered completely blind. We soon learned to distinguish between manhole covers in the middle of roads and those under sidewalks. We learned quickly not to attempt an exit from a manhole cover when speeding cars were rolling over it.
Jim eventually outfitted anyone invited to venture into our town's innards with rubber boots and what he termed "smoking jackets." A traditional smoking jacket is an overgarment designed to be worn while puffing pipes and cigars. Jim's version used thrift store suit jackets as mud and odor armor. Every mission explored further into the unknown. Self-appointed spies delving deeper into the cool down under, we discovered that by placing truck side-mirrors at key intersections, we could illuminate and see around corners. I'll never forget the thump the carriage made bumping over the tunnel's section seams.
Though the dank, decomposing odor was assuredly offensive to most, it smelled like adventure to us. It was all about conquering the next compartment, the next bend in the cave. And we were never deterred by the hollow glow of rats' eyes as they stared into the beams of our flashlights.
One eighth-grade afternoon, when we were nearing the end of this stage of subterranean delinquency, we emerged, resembling gnarly coal miners, from the manhole directly in front of the high school we'd eventually attend. There were four of us, as Jim had since built a second tunnel-rolling explorer. The entire cheerleading team, which was practicing on the lawn 20 feet away, froze and stared at us in our rubber boots and smoking jackets in a state of fear and confusion. Underclassmen to say the least, our fated 1975 arrival at the ankles of the Garden City High School cheerleaders would be a preset for how certain women would view me for the rest of my life.
Contemporary cavemen can still find their way. Travel is all about finding a light in the dark.
Travel writers and frequent adventurers tire of safety briefings before ziplining or whitewater rafting. Skydiving aside, sometimes you've got to learn as you go.
The term "snow skitching" is likely an alien one to anyone who didn't grow up with snowy winters in the 1970s. This is a wintertime snow-on-the-streets activity where a few pals innocuously wait at intersections with stop signs or red lights for cars to pull up. Once the car pauses, the crew of three or four sneak up behind the car, assume a squatting stance, and grab onto the car's rear bumper. The joyride begins as the car accelerates up to 40mph.
The dangers of this activity are numerous, but none is more perilous than cars passing over a warmer-than-the-pavement manhole cover exposed by melted snow. Ouch. Sometimes we must invent our own rites of passage.
Ultimately, hitchhiking made me. Enjoying a freestyle childhood, I began hitchhiking in seventh grade (and later to high school every day), which eventually led me across America and the world. It was my first entrée into travel. At 17, I played hooky from school for 10 days while bluffing to my parents about a fictional ski vacation, so I could hitchhike from Long Island to the Florida Keys, twice. That's when I knew that my life would unfold outside the mainstream. I would no longer be able to resist the instant rapport you can have with strangers while traveling. Free therapy—anonymous conversing—is often the best kind.
Hitchhiking to Brisbane to see AC/DC in 1988
Career travelers are often good at—or at least insistent upon—holding court, especially around tables of food or drink. When assembling groups of such personalities, this can also be a recipe for clashing open-road philosophies. A revelation occurred to me while attending a travel industry trade show in New York City. After being busted for eavesdropping on a conversation, I met two gentlemen about my age who were new members of the famed Explorers Club. Located on Manhattan's Upper East Side, The Explorers Club knows how to celebrate the old-style hardcore adventurer—pre-Gore-Tex. But my sense was that these members had never experienced the lost art of hitchhiking, which has been a rite of passage for many road warriors. Mark Twain, Jack Kerouac, Tim Cahill, and Paul Theroux are just some of the greats who come to mind. I asked the guys if they'd ever hitchhiked, and they said never.
Although I now believe that it's possible to find adventure while toting rolling luggage, it's hard for me to look another man in the eye and consider him a genuine adventurer if he has never had to make a hitchhiking sign and use it. (Understandably, hitching is less popular with women who are similarly on track to see the world.)
Because hitchhiking has earned a bad rap in recent decades, it now, unfortunately, only limps along as a way to make new friends, discover new places, and spawn authentic encounters bred on instant trust. It still won't cost you a penny. Between the ages of 12 and 35, I made hundreds of hitching signs that took me through every state, 10 Canadian provinces, and dozens of other countries. Hitching a ride defined my entertainment.
Debuting in 1980, CNN quickly drew an audience with its 24-hour newscast. Prior to that, the dissemination of bad news was limited to what a few antennae-fed networks could exaggerate regionally during their half-hour time slots. The ever-present news cycle, a contagion further escalated by CNN clones, soon became unavoidable. Until then, hitchhikers were still unannounced messengers of freedom, but the minute-by-minute news tsunami eventually insinuated—based on scant events—that hitchhikers were thieving and murderous types. The paranoia directed towards hitchhikers compounded as the armed robbery in the Southwest or the murder in the Northeast was now in everybody's living room. The art of hitching a ride got an F and was forever changed.
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