Chris McCandless and Cheryl Strayed: Tales of when Generation X wandered outside

I’m going to show my age a bit and talk about a particular time of transition.

If you grew up in the 1980s, chances are the stereotypes are pretty familiar: huge hair, lots of synthesizers, “greed is good,” and a general optimism that ended up giving us really bright colors in the stuff we wore and the things we had in our homes.

Most of the music sucked. At least I thought so. Even the hard rock and metal I listened to became overly formulaic — a few faster songs, the required power ballad, and vocalists trying to too hard to sound like Robert Plant in his Led Zeppelin II days. Every hair band was from the same cookie-cutter stamp, sort of like how country music artists are now.

At least we had hip-hop. That was original enough.

Then some things happened. We had riots in L.A., we went to war with Iraq and then had a recession. Crack cocaine went from being a Los Angeles/New York thing to a national dilemma, and crime soared. Suddenly all the factory-line optimism of the ’80s wore off, people started wearing flannel and music took a darker, more introspective and heavier tone.

We questioned everything, but not in the hippie, free-spirited way of the 1960s. Those guys/gals were our parents, and became fodder for our angst, by “our,” I’m talking about Generation X. We looked back at the glee of the 1980s and scoffed. No more Duran Duran or Poison. We were all about Nirvana and gangsta rap.

Some of us plowed through anyway. But some of us didn’t. Those few went a different direction. They went into the woods.

Hiking, backpacking, rock climbing — all those “adventure sports” that millions of people do now have always been there, but they just weren’t much of a thing for the masses until my generation came of age. I think it was partly a rejection of traditional sports (“ball sports” is how one doofus on MTV put it) and this funny fixation on “extreme” activities. “Extreme” being pretty much anything that involved jumping from a plane, hanging off a crag, riding your bike on dirt or doing something that could get you scuffed, hurt or killed without a ball being involved. That’s how it was billed, anyway. Never mind that people had been climbing, skydiving and getting “extreme” before that term became a marketing buzzword that got driven into the ground.

In any case, a good-sized chunk of Generation X got downright crunchy in the early 1990s, so much so that Nike started making hiking boots. Yeah, I bought a pair of those. They didn’t last long. But they did get me through a couple of alpine hikes in Montana as I hummed verses of “Under the Bridge” from the Red Hot Chili Peppers. It’s not like heroin addiction in L.A. had much of anything to do with Montana hiking (though heroin was definitely a thing in the 1990s), but it was a big song in a big time in my life when I reconnected with my outdoorsy self.

Others were a little more profoundly immersed in it. Two of them became the subjects of books — one a biography/adventure tale, and the other in an autobiography. One lived to tell that tale. The other died and became almost legendary to a lot of young, aspiring adventure seekers.

It’s probably not hard to figure out that I’m talking about Chris McCandless and Cheryl Strayed. And to be sure, their stories have been compared frequently enough.

But aside from the compelling tales of their lives, I want to be clear on this fact: Theirs are generational stories. They are very Generation X. And I guess that’s why they resonate so clearly with me. These were my contemporaries, in their early 20s, when their defining moments unfolded in ways that only now, years later, I can fully appreciate.

Chances are, you know their tales. McCandless, the subject of Jon Krakauer’s “Into the Wild,” rejected the life that was expected of him — college, then a job, then setting down with a family/house in the ‘burbs/career — and decided to wander the American West. He later took on an adventure in Alaska that, despite his pluck, took his life after a series of events, both of his own making and bad luck, proved too much.

Strayed, on the other hand, went into the woods on a whim to reset a life that had spiraled out of control. Unlike McCandless, she survived her foray into the Cascades, and came back a changed woman.

In McCandless’s case, the attraction to his story is hard to define. Certainly, the adept storytelling in Krakauer’s book – as well as some excellent reporting – has a lot to do with it. But there is more to it than that. A lot of the people who read the book felt drawn to wild places, to escape the endless sea of suburban rooftops and chain restaurants, unplug and test themselves in the wilderness. A few of those people make it a point to go to the bus where McCandless died, deep in the Alaskan bush. I get that, and so did a number of my contemporaries well before McCandless’s story became widely known. Hordes of us started disappearing into the backcountry before we knew who he was, mostly because we, as a generation, were seeking something, an experience of authenticity that was very anti-80s. Keep your “Lifestyles of the Rich and Famous,” Mr. Leach. Just give me a flat spot to pitch a tent and a crag to crawl on.

That’s what McCandless sought, to extremes. A quest for authentic self, straight from my generation to the pages of a book and eventually in the minds of millions who have carried that torch decades later.

Strayed’s story brought about something else, and I believe something wonderful. The book came out only a few years ago, though the events occurred about 20 years before. She was part of a new kind of woman that wanted to break the mold of what women could do.

Now to be sure, there have been some seriously legit outdoor women going back a long way. But there was a turn of mindset back then where a lot of women decided that they, too, could test themselves in the wild. Male-dominated activities like backpacking, rock climbing and mountaineering saw an influx of female powerhouses as well as legions of everyday adventurers suddenly come forward. That has its roots well before Generation X took a breath, but the idea of women doing big things outdoors seemed to take flight somewhere around the time Strayed was lugging Monster around on her back, trekking north through the Sierras and learning a lot about the do’s and don’ts of how to make it on an 1,100-mile through-hike.

Now her book (a fantastic read, by the way) is a movie, and people are expecting a big influx of would-be “Wild” hikers to test themselves on the Pacific Crest Trail. In between the movie’s release and Strayed’s hike, growing numbers of women have been getting after it outside, to the point now where gear manufacturers  live and die not just by how good their products are, but how well they can reach and please a growing demographic of female outdoor adventurers. Strayed’s tale may not be unique, but it is emblematic.

So what does all this mean, and how does it relate to Generation X? In McCandless’s case, I’d say it reflected a general dissatisfaction with what proved to be an illusion of what American life offered. Naturally, the preferred escape route was the opposite of where we came from. We fled the cities and small towns and the expectations their denizens had of us, and we went into beautiful, indifferent and difficult places outside. That sentiment has always been there, but I’d say it’s never been more prevalent than it is now, going back to those times when we were all spinning Pearl Jam CDs for the first time.

And in Strayed’s case, it marked the beginning of the ubiquity of the outdoor woman. The guys may still outnumber the ladies when it comes to getting dirty in the woods, but the playing field out there is quite level now and fewer people question why a woman would get all scraped up climbing a big wall or spend days out on the trail by themselves. The oddity of old is now more routine. I’ve seen it, and seen it for years. Strayed’s adventure embodied empowerment of women in the outdoors.

For me personally, the common strains of their stories resonate deeply. When surrounded by the trappings (handcuffs?) of “normal” life, I feel that urge to jump in the car, load a pack and head west until I see towering peaks and a singletrack trail leading into who knows what. I feel the need to hear birds, streams, and, at times, nothing at all. A quiet retreat where I can unload my burdens into an eternal place that’s been around well before I was born and will be around long after I’m gone. I feel the need to empty myself through exertion, to solve atypical problems with only my wits and whatever I’ve hauled in on my back.

Peace comes out of that. A little meaning. And empowerment. Maybe the same tunes were running through Chris’s and Cheryl’s ears as they ventured out that first time, when we fled the plastic excess of the 1980s and headed outside – who knew that our stories might change the way people interacted with the wild.

Bob Doucette