Before the bear came it was a grab bag of small miseries—the standard discomforts of a coastal person who basically spends his time inside. I wasn’t sure if I had gotten any sleep. My pack’s straps had abraded symmetric blisters on my collarbone. I had tweaked my back by lying on my side, and my legs by curling them up. I needed to go to the bathroom but kept deciding that it wasn’t worth the trouble. My body temperature had been oscillating wildly: I’d been getting cold, then putting on a layer or two, then sweating, then dropping into chills. And my stomach was churning—I hoped not from “beaver fever.”

But then, panic. A pounding, spiraling, helpless panic, the kind you might feel—that I once did feel—when bracing for impact on an airplane about to make an emergency landing.

Just outside our three-man tent I had heard the signatures of ursine curiosity: heavy footsteps, panting, and every so often a terrible silence in which the two of us, the thing and I, would freeze, and tighten, and turn the dials way up on all our senses and wonder what sort of mind was likewise poised on the other side of the thin fabric.

I had no useful equipment inside the tent and no plan and so I simply sat there and feared, and between the fearing hoped, this hope consisting in the image of dawn breaking, and the other guys waking up, and a swift hike through berry thickets back to our minivan, 5.2 miles away, where I’d find my way to the nearest town and get me some ostentatious comfort, something like a massage and an episode of Cheers. No, I thought, camping is not manful adventure, it’s misery—and the only tolerable risk of a bear attack is exactly zero.

This was a revolution in my thinking from even just a day before. That the western side of Glacier National Park was dense with bears was clear enough from the maps and signs, and clearer still from the dozen clumps of fresh scat along a nearby trail. My friend saw one just outside the campsite; so did that couple—they said it was massive. They said, too, that they heard another one poking around last night. In fact this place was so conspicuously teeming with bears that in the event of my tragic mauling my family and friends could very sensibly think to themselves, “He was asking for it.”

And of course I was.

NOT TOO LONG AGO I was in a Starbucks near New York University waiting to use the bathroom. A young guy about my age comes out. I see that he’s carrying an oversized colorful object, so I ask him, “Is that the bathroom key?” and he says, “Yeah, it is.” This is some kind of luck, because most times when a Starbucks bathroom requires a key, you don’t know it until you get to the door—and then you have to go ask someone at the register for it.

“Do you mind if I grab that from you?”

“Actually,” he said, “I need it to get my ID back.”

That killed me. Not because of anything he did, of course. It killed me because learning that I needed a license to pee was a reminder that for the privilege of living on a small island with four million people I have traded in some things, and the most precious of these is freedom.

“I wish to speak a word for nature,” Henry David Thoreau began an 1862 essay on walking, “for absolute freedom and wildness, as contrasted with a freedom and culture merely civil,—to regard man as an inhabitant, or a part and parcel of nature, rather than a member of society.”

By any civil standard I am a very free man. But Thoreau would call me a zoo animal if he saw me handing my photo ID to a barista. “In wildness is the preservation of the world,” he wrote. “Dullness is but another name for tameness.” What kind of freedom is it if you spend the daylight hours indoors, in managed places, crowded and rule-bound?

I work, for instance, as a Web developer. It’s a very good job. Our office is a block south of Union Square, a 12-minute commute from my apartment. We’re served breakfast every morning. Our kitchen is stocked with “provisions” of organic beef jerky, coconut water, craft beers, chips, and two restaurant-class espresso machines. We have two ping pong tables and buckets of 3-star ping pong balls. (A new office manager bought “1-stars” once and some of the guys protested by crushing them.) We work on 4-cored Apple Mac computers with dual monitors. We have an unmolested hour for lunch, 10-minute breaks in the morning and afternoon, and a “do not disturb” policy past the working hours. We even have a specific email address where employees can ask for free things: genuine maple syrup, hot chocolate, a $900 chair, a new keyboard. Most of the programmers make six figures, and many of those have only three or four years of experience.

It’s impossible to say so without sounding like the spokesperson for Entitlement itself but working there is still sort of soul-crushing. It’s soul-crushing in the way that any job that doesn’t command your full passionate attention must be. What happens is that I will be in my chair in the early afternoon and I will accidentally step out of myself and all I’ll see is time passing, nine-hour parcels of healthy consciousness forever being packed away as the user experience of clerical workers or consumers or whoever gets marginally better; and I’ll end up thinking that this enterprise of mine is not so much creative but bureaucratic, that what I’ve gotten good at is reading the instruction manuals of other people, finding my way around their insignificant warrens. And in those moments the whole business will seem to me like kind of a tragic waste.

A lot of people would no doubt tell me to grow up and be a professional. Thoreau would tell me to go outside. “I think that I cannot preserve my health and spirits unless I spend four hours a day at least—and it is commonly more than that—sauntering through the woods and over the hills and fields, absolutely free from all worldly engagements....”

"For I believe that climate does thus react on man—as there is something in the mountain air that feeds the spirit and inspires. Will not man grow to greater perfection intellectually as well as physically under these influences? Or is it unimportant how many foggy days there are in his life? I trust that we shall be more imaginative; that our thoughts will be clearer, fresher and more ethereal, as our sky. ... Perchance there will appear to the traveller something, he knows not what, of læta and glabra—of joyous and serene, in our very faces. Else, to what end does the world go on, and why was America discovered?"

HERE’S A THOUGHT THAT’S been getting me down lately living in New York. Suppose that I wanted to climb a tree. Where would I go? Do I have to make a plan? Central Park has a lot of trees, but I don’t think you’re allowed to climb those. Maybe there is a business that has gotten permission from the city to take people to trees that are good for climbing, and that will teach you how to do it safely, for $50 with tax and lunch included.

This is how I have come to think. I have become too much a friend to rules; I have slept for too long in a soft bed; I have grown quite comfortably into the rites of a civilized life and as a result I think I have become something of a fucking infant. And what’s worse is that when I look for a way out all I see is the very thing I’m trying to escape: planned activities, waivers, check-ins and permits—the bathroom keys of the great outdoors.

The trouble is, nature does not come naturally to people in my world. It is not something we just do, like walk. It’s a thing we sign up for, train for, save for—like, say, hockey. For us, going outside is a sport.

The best evidence of this is the fact that our first stop is always to a sporting goods store, a place like REI, the Recreational Equipment Inc. (motto: “Get outside yourself”). A store that—before it can sell you anything else—must sell you the idea that you need to “gear up” to go outdoors.

Their trick is to convince you of the inadequacy of the equipment you already own. At REI you learn that your baseball cap is defective because it doesn’t have a certified ultraviolet protection factor. You learn that your matches aren’t stormproof and that a $25 Strikeforce firesteel will more reliably give you “intense sparks” than even stormproof matches. You learn that socks have temperature ratings, that freeze-dried food offers the most calories for its weight, and that whatever you were planning to use to cook your food, freeze-dried or not, it probably can’t also charge your iPhone (Biolite Campstove, $129). You learn, basically, that if you were to take old John Muir’s lead and roam around the High Sierra with nothing but a notebook and bread tied to your belt you would probably die.

The problem isn’t that the gear is unnecessary or overpriced—in fact, reviews of the few items I named are overwhelmingly positive; and of course durable, lightweight clothing and equipment is essential—it’s that for a person looking to nature as an escape from things like marketing departments, composite fibers endorsed by Bear Grylls have a way of breaking the spell. They come at the worst possible moment: right when you’ve become sufficiently fed up with the local civilizing forces to grope for wildness, there you are at a store again, playing customer again, a game that in this context is especially nefarious because the other team so knowingly preys on your craving for its opposite, for something real, and natural, and hard. For the authentic wild.

IN A 1999 ARTICLE for Time magazine entitled “Will There Be Any Wilderness Left?” Jon Krakauer argued that no, there will not be. The trouble is that too many people want to go. Modern transportation has made the wild more accessible. Madison Avenue has made it more attractive. There is in fact a “wilderness fad,” Krakauer argued, and it’s killing the very thing it celebrates.

“As more and more people flock to the backcountry,” he wrote, “habitat for native plants and wildlife is inevitably compromised. To safeguard natural habitat, it becomes necessary for government agencies to exercise intervention and control. Inevitably, and justifiably, strict limits are placed on backcountry use.... Of course, when wilderness is so intensely managed, it ceases to be wild. It becomes a toothless simulacrum. It becomes a park.”

“Exactly,” I find myself saying. “This is exactly what I’m talking about.”

But it’s strange that I should even care. I am no Jon Krakauer—an author best known for Into Thin Air, his account of the 1996 Mount Everest disaster that killed eight climbers in one day. Jon Krakauer has cause to call the American backcountry “a toothless simulacrum,” because Jon Krakauer knows what teeth look like.

By contrast, the closest thing I’ve seen to a disaster outdoors was when my brother sliced his fingers on an open blade while reaching into my backpack for some wieners. We were about to cook them on a small (and illegal) open fire on a beach in western British Columbia. To get to the hospital we had to climb a few short crags over knee-high waves. He ended up with five stitches.

I haven’t been to wild places. I couldn’t tell you what they’re like. Why should I care that they might be softening up? I am awfully soft myself.

In fact, I am almost certainly one of the trendy bastards Krakauer is bemoaning in his essay: a young man sold on wilderness through some combination of early American philosophy and Dodge Ram commercials whose enthusiasm is mostly just irritating until it gets on a bus with 30 other irritating enthusiasms. Then it gets destructive. Because then it’s leaving its trash behind and tamping down trail, attracting rodentia with its indiscriminate piss—spoiling good things with its good intentions.

I REMEMBER WHEN I first started drinking coffee how proud I was that I took it black. And the first time I put sugar in it, how proud I was to be using the raw brown kind. Look at those crystals, I thought. Look at that real sugar.

It’s like what’ll sometimes happen when I apply my “original scent” Old Spice in the morning. I will think to myself, not explicitly, but in a small, subtle way, Thank God I’m not one of these assholes wearing Axe. How proud I am to resist the ethos of that brand—a Bud Light, frat boy ethos: “this deodorant will get you laid”—to instead be wearing the simple scent my father wore, the scent his father wore, back when young American men were dying in important wars.

This is what quiet desperation looks like. Days filled with small self-affirmations, gestures toward some ineffable significant thing. It’s insecurity, basically, mixed with nostalgia. It’s what a hipster does—he “fetishizes the authentic.” And he does this—I do this—because nowadays authenticity is so hard to come by.

In a radio interview, the author David Foster Wallace described a culture where “everything is rhetoricized, and everything has an element of presentation and interpretation and sales pitch, and this mental chess where, before I say the thing, I already scan and triage your possible responses to it, and my responses to those responses, and the portraits we’re gonna get of each other from what we’re gonna say....”

“I’m not a great historian,” he continued, “but as far as I can see not since the Sophists, in Athens, has there been this rapacious and effective and widespread rhetoricizing, performance, and review, and me-watching-you-watching-me-watching-you–type metastasis in a vibrant culture.”

That’s the right word, I think: “metastasis.” It’s a cancer, this festering thing that begins as insecurity and narcissistic preening and mutates into an always-on performance and a hunch that everyone else is performing too. And so you develop an eye for affectation. You doubt motives in general. You become Holden Caulfield:

"Even if you did go around saving guys’ lives and all, how would you know if you did it because you really wanted to save guys’ lives, or because you did it because what you really wanted to do was be a terrific lawyer, with everybody slapping you on the back and congratulating you in court when the goddam trial was over."

Everyone is acting, you think—even the guy who buys clothes with no labels on them is curating a personal brand, self-consciously seeking self-definition. You channel Franny, another young Salinger character. “I’m just sick of ego, ego, ego,” you say. “My own and everybody else’s.”

And there comes easy old genuine nature, offering its escape.

“Another glorious Sierra day in which one seems to be dissolved and absorbed and sent pulsing onward we know not where,” John Muir, the founder of the Sierra Club, put down in his journal on June 13, 1869, while trailing a shepherd and his flock to the source of the Tuolumne river. “Life seems neither long nor short, and we take no more heed to save time or make haste than do the trees and stars. This is true freedom, a good practical sort of immortality.”

Which is so much the essence of what I’m looking for that it is at once a promise and a terrible challenge—terrible because however much I want to go with Muir and feel full and in the moment I may not, by my very constitution, be able to. It may well be that even as I embark on a trip into the wild, especially as I embark on one, I am doing no more than configuring my public self. It may be that it’s simply not possible for me to go genuinely, unselfconsciously outside.

Consider, for example, the time I drove up to New Hampshire alone and stayed in a cabin owned by Dartmouth college, paying $20 a night, bringing nothing but food, clothing, and a couple of notebooks. Was there even one moment of that trip that wasn’t an embarrassing cliché? Was there one moment where I was doing something with no regard for what other people might think when I told them I’d done it?

That’s the paradox. In a culture pervaded by artifice, by self-awareness and advertising, the grand gesture away from it all—“Fuck it, I’m going into the wild”—is just another trope. We’ve seen that movie. In fact it was called Into the Wild and for the parties involved it was sort of a pathetic catastrophe.

This is the bind I’m in: I feel small in urban life—“tired, nerve-shaken, over-civilized,” as Muir put it. I want to get away for a bit. I’m inspired by Thoreau and company to get really away. But in the very breath of my demand for the “authentic” wild, the un-guided tour, I’m cringing at how flaccid and disgracefully naive I probably sound—how much like one of Krakauer’s goons, the kind of person who will either gentrify the woods or get myself killed in them. This reaching toward the outdoors, far from clearing my head, confounds it further. This deep-seeming thing I crave may well not exist. Or worse, it does—and I’m too bound up by ego to seize it.

I REALIZED THE BIG attraction might be that my friend was snoring, so I pushed at him a little until he got quiet. To my surprise, it worked: that was the last I heard of the bear.

I had no sense of the time. I hoped it was late, because I was still alert, still listening to the night the way you do when there are sounds you’re desperate not to hear.

And how grateful I was after nothing but sleeping bags rustling and distant twigs shifting to hear the enormous sound of a wind coming in over the mountains. It hadn’t gotten any brighter but the sun, I guessed, must have been rising just east of us—we were in a small lakeside campground west of the range that divides Glacier Park into halves—and giving the ground there a gentle bake. The temperature difference between that side and this one would mean a pressure difference, too, enough to make the air move.

Birds chirping a few minutes later confirmed that indeed it was morning, and that I would soon be back from the backcountry.

FIVE GOOD FRIENDS WHO had been friends for more than a decade had just spent three full days and nights together, on vacation, with nobody else for miles, and between us there hadn’t been a single conversation. We had made small observations here and there and sounded instructions to one another but it wasn’t until we had settled on the fourth night into a big frontcountry campground—a place with potable water, garbage cans, a grill over the firepit, a flush toilet, sinks, mirrors, access to emergency services, ice, other people, and a supermarket—that we really began to talk.

For my part it was fear and exhaustion that had kept me quiet.

Our hikes had been more like marches. We weren’t enjoying nature, we were trying to get through it. We were trudging on a narrow overgrown trail from one campsite to the other, each about six miles away from the last. Our pace was two miles an hour. Between sites there was no room to stop; the best we could do was pause in a single file.

This was not the kind of walking, mind you, that Thoreau described—we were not sauntering. We moved like rusty train cars. Every hundred yards or so one of us would clap or yell so as not to come up silently on a grizzly. Our packs were heavy. Our feet hurt. Our minds were mostly blank, not in the good zen way, but in the way of people whose whole tired attention is on the ground in front of them.

At every moment some minor hitch—a cut, burn, unclean water, dehydration, a slip, a turned ankle, the flu, a wild animal, the cold—threatened to create a major situation. We were eight hours of heavy hiking away from a van that was itself another two hours away from a town or ranger station. We had no way to call for help should something happen.

In exchange we were met at each campsite by a lake filled with very cold water. I enjoyed these lakes: they were beautiful, calm, framed by mountains. At one I even went for a dip; it was exhilarating. But was that it? Was that why we had come here?

I kept the questions to myself until we got back to the frontcountry. Beer in hand, burger in stomach, I finally felt safe and energetic enough to say, “I am tired of being outside.”

IT’S IRONIC THAT I ended up being the first of the five of us to talk about staying in a motel, or to suggest we finish our trip with a guided kayaking tour. (One of the guys said that it was me who had “broken the seal on being a bitch.”) It’s ironic because earlier in the summer I had been so passionate about doing something difficult with no help. “The goal is not to get raped by bandit locals,” I had written in an email, “but I think it would be more fun to just e.g. strap a canoe to our car, bring a couple of tents, and make our way down a river using a map. The fact that it’s not immediately obvious how we’d do that is sort of depressing, but God forgive us if we can’t figure it out.”

It’s ironic, but it’s not very interesting. “Overeager urbanite flounders in the woods” is in fact the kind of obvious template that works well as a sitcom arc. As such, it’s easy to laugh off: Yes, I’m the nitwit who talked up going into bear country and then got really terrified of bears. So what?

The real irony—the irony that matters, because it actually hurts—is what happened on the east side of Glacier, the side with the easy hikes and beautiful views.

I was so ready to be at my best in that place. I am, after all, the sort of person who sees himself hemmed in by the city; who has always felt a kinship with Emerson, Thoreau, Whitman; who moved from Canada to America with no small amount of proud nostalgia about the Great White North. Doesn’t that make me just the sort of person who would know what to do with “the best care-killing scenery on the continent,” as Muir put it? Who when he got there would exalt the way Muir did?

"The air is distinctly fragrant with balsam and resin and mint,—every breath of it a gift we may well thank God for. Who could ever guess that so rough a wilderness should yet be so fine, so full of good things. One seems to be in a majestic domed pavilion in which a grand play is being acted with scenery and music and incense,—all the furniture and action so interesting we are in no danger of being called on to endure one dull moment. God himself seems to be always doing his best here, working like a man in a glow of enthusiasm."

And true, every so often on the Highline Trail—a 7.6-mile hike at about 7,000 feet—I would look to my left at the glaciers, the lakes in the distance, the bighorn sheep on green hillsides, and of course at the mountains, those old men with forest beards, their peaks wise to the high air, and I would practically yip at how pristine and vital it all was. “This,” I wanted to answer Thoreau, “this was why America was discovered.” Thank God I’m here to see it.

But for the most part I just sort of moseyed as the unbelievable majesty and perfection of the scene beside me became a kind of pleasant wallpaper. The life never drained out of it the way that, say, it drains out of a song I listen to too many times in a row. But there was no ecstasy in it. It was pretty, that’s all, just like a pretty girl. It glowed with something good; I could look at it all day. But it wasn’t a religious experience.

“We saw another party of Yosemite tourists to-day,” Muir had written in his journal. “Somehow most of these travelers seem to care but little for the glorious objects about them, though enough to spend time and money and endure long rides to see the famous valley.”

ANY GOLFER WILL TELL you that if you went to the driving range and duffed it a hundred times, and then hit a pure one, and then duffed it a hundred times more, what you ultimately had was one hell of a good shot.

And so it goes with going outside.

It’s true that I don’t have John Muir’s vision. But by the time he was 11 Muir “could recite the New Testament from the beginning of Matthew to the end of Revelation without a single stop.” Where I was biking around cities or playing video games he was climbing up the sides of Scottish castles and hunting birds’ nests in the countryside. It takes a special kind of upbringing and a whole lot of work to develop an imagination that gets pounded by a thunderstorm and delights in the lifecycle of a single raindrop. Muir was not just born mindful of nature, he was fastidious throughout his life in the study of botany, geology, theology, biology, ecology, in the languages of man and God that make the whole world pulse with meaning.

My mistake in Glacier was not in failing to appreciate the high flowers, the playful lives of the squirrels; it was in thinking that such an appreciation would come naturally.

I shouldn’t be so hard on myself. At the very least I listened one morning to the ground wake up. I felt something when I looked into the eyes of big mountains. The rest will come with practice. Just as classical piano puts me to sleep because I don’t know how to listen to it, so, too, will the best parts of this country have all the impact of a postcard—until I learn how to look at them.

Yes, I am soft: I had trouble sleeping on the freezing Montana plains; I panicked at the sound of an animal outside my tent; I got tired of carrying a heavy pack. But we went 12 miles out unguided, and I dove headfirst into a very cold lake, and those are pure enough swings for now. My back will harden the more I lie on the hard ground.

And yes, my friends and I took many pictures of our outdoorsy vacation, and the moment we got back, most of us, I think, felt an urge to get those pictures up onto Facebook. In fact, I made one of them my profile picture, a shot I had clearly posed for. What that tells you is that nature does not, on its own, have the special power to free a needy ego. But does it tell you that my hankering for the American wild is entirely an affectation?

I’m reminded of when my godfather took me out on my eighth birthday for a walk in the woods north of Montreal. I hadn’t really been into the woods before—not like this, just wandering around. I remember that it started to rain, and I remember that we got lost. I was scared but thrilled; as I toddled behind him I kept yelling that this was the best birthday present I’d ever gotten. And some part of the thrill, no doubt, even as an eight-year-old, was this picture I had of both of us returning to a house full of people who had stayed in, and beaming about our mild adventure. But by far the larger part was that this was a mild adventure—a respite from a fragile boyhood, a taste of the real.