Revisiting Generation X

When I first read Douglas Coupland’s Generation X, I had this sensation of discovering the source of something I’d already encountered everywhere else. Reality Bites, Clerks, Singles, Empire Records — all different movies, different stories, but sharing something in their attitudes toward the world: the sarcasm, the irony, the studied indifference toward the things adults were supposed to want. Reading Coupland felt like finding the spring from which they all emerged. For me, his book explained something the movies were depicting only partially, and to do so with an authenticity that made the films feel like performances.¹I think in large part because they were trying to squeeze some kind of lesson out.

There was something enormously attractive to me about his characters’ detachment from the conventional measures of success. Titles, money, possessions, advancement: they seemed to have concluded that these objectives were insufficient reasons to organize a life around, and had decided to move forward accordingly. Even their apparent lack of ambition seemed ambitious in its own twisted way. There was something aspirational about their willingness to arrange their lives around that recognition.

I was nineteen. My understanding of what a successful adult life might look like was still largely hypothetical. But I’d arrived at nineteen in a culture increasingly skeptical of the guarantee that doing everything right would necessarily get you anywhere worth meaning.

What struck me most about Generation X was that Coupland didn’t seem particularly interested in explaining that skepticism. There was no voice standing above the characters, telling us what to make of their circumstances or pointing out the flaws in their worldview. The characters talked, told stories, made observations, and occasionally seemed just as uncertain about their motivations as I was about mine. I still have many of my journals from that time. In one entry, I described the book as “reflections on a fallen culture.” I’m not sure I could have explained precisely what I meant by that, but I was sufficiently taken with the thought to write it down.

I recently found myself in a conversation with a friend about how sterile city centers have become. The disappearance of local character, the creeping sameness of commercial franchises, the strange phenomenon of traveling thousands of miles only to encounter a slightly rearranged collection of the same stores and restaurants.

For reasons I can’t explain, I remembered a passage from Generation X. One of the characters is thinking about the distinctive smells of cities. Tokyo smells of noodle broth, sewage, chocolate, and exhaust. Milan of cinnamon, diesel, and roses. Vancouver of roast pork, salt water, and cedar. Portland of trees, rust, and moss. I went looking for the passage, found it, and started reading.

It was a strange experience. The world of the book felt almost impossibly distant. The preoccupations, the vocabulary, the particular flavor of resignation. Even the way the characters performed their rejection of conventional success seemed like something that belonged to a vanished culture. I recognized them … I had known variations of these people, or people who admired them, or people who enjoyed pretending to be them. But I don’t know that I know anyone quite like them anymore. Even the people I remember from that time have become different people.

And yet the familiarity was visceral. Not quite nostalgia, though. I don’t particularly miss the world the book describes, and I’m not sure I ever wanted to inhabit it. But I remembered what it was like to be near it. To recognize its assumptions without having to explain them. To hear certain things said and understand immediately what kind of person was saying them. There’s an odd sensation in recognizing a place you no longer belong, particularly when you aren’t especially interested in returning. The familiarity survives the desire. I’m sure the Germans or the French have a term for that feeling.

I keep hearing variations on a familiar conversation about young people and work. They’re less ambitious, less willing to make sacrifices, suspicious of traditional careers, perhaps too concerned with finding meaning in something that is, after all, a job. It’s not quite the slacker critique of the early 1990s, but there’s a family resemblance. In both cases, the attitudes of young people become objects of scrutiny at almost precisely the moment when the economic terms of their participation in professional life are being reconsidered.

There’s an interesting dialogue between these things. The cynicism and detachment of the early 1990s weren’t simply products of recession and corporate downsizing of that era. They were also fashions, cultural expressions, even identities to inhabit. Some of the skepticism was earned, some inherited, some perhaps just appealing. But neither did those attitudes emerge independently of the economic uncertainty that surrounded them. Neither explains the other entirely, but it’s difficult to imagine either conversation unfolding quite the same way without the other.

In the early 1990s, the business conversation was dominated by recession, restructuring, and the changing economics of corporate employment. Today, AI and productivity increasingly frame a similar business-centric discussion about which workers organizations need, particularly those just beginning their careers. Different circumstances, different mechanisms, but in both cases, employers are reconsidering their relationship with a workforce whose own expectations of work are simultaneously being questioned.

Something about that relationship feels familiar in Coupland’s characters, even if their particular expression of it now seems so remote. How people come to understand ambition, success, or even the value of work while the institutions they expect to participate in are changing the terms of that participation is weirdly contemporary.

I was a high school freshman when Generation X was published, which meant I got to be immersed in the worldview of the book’s characters without being particularly qualified to evaluate it. Grunge had displaced the glossy confidence of the preceding decade. Sarcasm and irony were practically a dress code. Detachment was something you could wear, and it carried a certain prestige precisely because it purported not to care about prestige.

I’m sure I wouldn’t have described it this way at the time. High school felt, among other things, like an extended exercise in trying on identities to see which ones fit. And these identities were coded cool. The most appealing thing about them was that they didn’t seem to care about being cool, an attitude that required considerably more effort to maintain than it was socially acceptable to acknowledge.

Authenticity was enormously important, even if its expression was obviously borrowed from somewhere else. I remember the distinction between being called a poser and being called a sellout. Neither was complimentary, but the latter carried a much more serious accusation. A poser was pretending to belong. A sellout had betrayed something by deciding that money or success mattered more.

I still recognize that hierarchy of sins in myself, which is interesting to confront thirty-five years later. I wonder sometimes what my children’s generation regards as similarly unforgivable, or whether the emphasis on authenticity has acquired an entirely different vocabulary.

But the cultural sensibility wasn’t simply aesthetic. I remember the Gulf War as an enormous event, and the broader sense of uncertainty that surrounded the early 1990s. I remember news stories about the economy and about college graduates struggling to find work. I remember the 1992 election and the extraordinary context compressed in the line “It’s the economy, stupid.” It seemed to substantiate something that was in the air.

I had begun to entertain a troubling question, as a first-generation college aspirant: What if college won’t pay off? Not that I was considering skipping it. College was still the necessary next step, but the idea that I might be entering a step that was the surest path to success right at a time it might betray that promise was unsettling. I hadn’t earned that anxiety through experience. It arrived secondhand, through television, magazines, music, the people around me, and the general atmosphere of the period. Which doesn’t mean it wasn’t real.

When I encountered Generation X a few years later, it gave language and characters to something I’d previously known only as a vibe.

It’s strange how rarely a popular novel gets to become a kind of documentary history.

Not because Coupland was recording events with documentary precision. The whole book is a work of artifice — it is literally fiction. But it preserves something that more conventional historical accounts have difficulty recovering: the experience of a moment before the people inhabiting it knew the significance of what the moment would become. Generation X wasn’t written with the benefit of knowing what happened after 1991. It was concerned with the present, almost obsessively so. Its marginal definitions, cartoons, consumer references, and invented terminology were attempts to describe a world that was happening as the book was being written.

Much of what makes it feel unconnected to today is exactly what gives it this documentary quality. An economic history of the early 1990s can explain the recession, corporate restructuring, and the changes underway in American employment. We can now place those developments alongside the subsequent technology boom, the dot-com crash, and the emergence of an economy that would eventually reorganize enormous portions of everyday life.

Coupland couldn’t, and didn’t try. His characters weren’t waiting for the next economic transformation. They weren’t early representatives of a cultural movement whose significance was waiting to be discovered. They were people inhabiting a particular present, constructing stories and explanations that made sense to them within it. Their detachment, their skepticism, even their fatalism existed without a need to lead anywhere.

I actually encountered Coupland through Microserfs, published in 1995, which I read during the summer before my sophomore year in college. I loved it enough that I went looking for his earlier work. Microserfs felt like it was speaking directly to me, or rather an aspirational career-oriented dimension of me. Its characters were older, already working professionally in the technology industry, negotiating lives built around a medium I was only beginning to understand. Their relationships with work were complicated².A really interesting book in its own right, and one that provided me a healthy perspective about the power and limits of work-as-purpose as I navigated the dot com bust a few years later. The boundaries between their personal and professional identities were blurry, and the possibility of doing something independently seemed to offer an escape from an organizational culture that was simultaneously exhilarating and suffocating. There was something recognizable in their enthusiasm and something tantalizing about their proximity to an actual professional life in technology.

Generation X, by contrast, described an attitude I understood but a world that already seemed to be receding. Four years separated them, but to me they inhabited markedly different places in the cultural imagination. They described overlapping conditions that were still active around me, even if I was standing at different distances from each.

It’s difficult now not to arrange them into a progression. The rejection of conventional ambition in Generation X, followed by the emergence of a new kind of ambition in Microserfs. The retreat from corporate life, followed by the possibility of building something outside its established structures. It’s an attractive sequence. Particularly knowing what happened over the subsequent decade.

In the fall of 1994, I moved into a dorm at the University at Albany that had been the first on campus wired for high-speed internet, the preceding spring. The university had installed DEC desktop computers in each suite, intended to give students access to university services without requiring a trip to the computer halls. The connection was a T1, which at the time felt stupidly fast compared to 14.4 modems.

I was living with and around computer science students who were losing their minds over what was becoming possible. Gopher. Telnet. FTP. Newsgroups. NCSA Mosaic. Cello. An assortment of applications and protocols that consumed an astonishing amount of time, competing only with MTV’s near-continuous rotation of Doll Parts and Zombie. There was also the weekly ritual of watching My So-Called Life.

My journal suggests that by October 16, I started using a beta version of what would become Mosaic Netscape, released only days earlier. By December, one of my dorm mates, a computer science major, showed me the basics of HTML and explained how to configure my university VAX account to expose a public directory containing web pages. I made one.

It was almost certainly terrible.³I feel very lucky that the internet doesn’t have a memory that goes this far back. Embarrassment into the dustbin of extinction. I’m pretty sure it was an introduction to who I was, what I was studying, and some experiments with heading tags to see what different sizes of type looked like. The page is lost, apart from a few references in my journal, but I remember the sensation of discovering that I could put something on a computer and make it available to people I had never met.

I had, in my mind at least, acquired a printing press. Not metaphorically in the sense that the internet might someday revolutionize media, commerce, communication, and political life. I mean that I understood, with a type of clarity that I’ve felt only a few times since, that I could publish. The ability to make something and distribute it without asking anyone’s permission was suddenly available to a nineteen-year-old sitting in a dorm room. That was an extraordinary high.

By then the university was selling network cards to students who wanted to connect their own machines. I installed one in my homebuilt DX33 running Windows 3.11 (for Workgroups) and Winsock, and suddenly the internet wasn’t something I visited on the DEC in the common area. It was mine, on my own computer, whenever I wanted it. In my own way, “jacked into a custom cyberspace deck”⁴.It’s impossible to talk about the early internet and futuristic projections about it without a Neuromancer reference.

We were playing Doom across the local network, which was probably just as compelling at the time as the intellectual possibilities of distributed publishing. By the spring of 1995, I was completely absorbed by the possibilities of connected technology. It was a social feeling in my dorm that echoed what was happening in my classrooms, about discovering and learning extraordinary new capabilities and starting to imagine things I might do with them.

I think that feeling is still there inside me three decades later.

Reading Microserfs that summer was exhilarating because its characters were inhabiting a world I could imagine entering. They were working in the medium I was discovering, confronting the opportunities and compromises that came with making it their professional lives. But neither the book nor my enthusiasm gave me any particular insight into how consequential that medium would become. The dot-com boom wasn’t clearly inevitable to me in 1995; I just knew the internet mattered. I had very little idea what it would come to mean to everyone else. The speculative excesses of the late 1990s, and their collapse, demonstrated how wildly premature many of the assumptions about the internet’s economics had been.⁵But without that collapse, and the timing in which my own career temporarily went dot com bust, I have a hard time imagining being as satisfied in the now. Very Sliding Doors.

Reading Generation X right afterward felt grounding; ambition wouldn’t automatically be met with opportunity, optimism might never encounter a world prepared to reward it. The book’s conversations seemed to tell me, “Focus on what interests you, because at least you’re doing something you care about.”

There are books I’ve read since that offer more structured ways of understanding what happened during those years. AnnaLee Saxenian’s Regional Advantage, with its contrast between the organizational cultures of Route 128 and Silicon Valley. Fred Turner’s From Counterculture to Cyberculture, tracing the movement of ideas about autonomy, community, and technology into the emerging digital world. The New Spirit of Capitalism, with its account of capitalism’s remarkable ability to absorb elements of the critiques directed against it.

Sometimes I find it unsettling how many of these works have shaped my understanding of the professional world I’ve been navigating. They gave me language for things I witnessed before I had language for them. They also made it remarkably easy to arrange the past into a persuasive narrative. The story almost tells itself. The disaffection of the early 1990s, the rejection of conventional corporate ambition, followed by the emergence of a technology culture offering what seemed like an entirely different relationship with work. Smaller, flatter organizations. Entrepreneurship. Creativity. Autonomy. The possibility of deriving meaning from the things you were helping to build. I can look backward now and imagine that the shape the technology industry took was almost an answer to the slacker criticism of work.

The trouble is that I know how the story turned out. Or enough of it to make the connections more deliberate than they probably were. When I read Microserfs in 1995, it wasn’t describing an established alternative to the corporate world, but people experimenting with one. And when I read Generation X afterward, I didn’t see it as the cultural prequel to that experiment. Both books were describing worlds I recognized, even if I was standing at different distances from each.

And now, thirty-one years later, I’m having a hard time shaking the resemblance between the conversation about young people and work then and the one happening today. Institutions rethinking the economics of employing people just as the people entering those institutions are being criticized for their attitudes toward work. Different circumstances, different motivations, different technologies. Yet something about that conversation sounds familiar enough that I find myself wondering whether we’re evaluating the prospects of an emerging generation through an organizational model that may itself be losing relevance.

Rereading Generation X grounded me in something important: the experience of living through a moment is nothing like the experience of explaining it afterward. I didn’t encounter the book as a portrait of an old world waiting to be replaced. I encountered it as a convincing description of a world that was still partly mine. Now the novel feels historical, even as something about its uncertainty seems familiar again. And I recognize how attractive that historical rhyme can be.

I’ve spent most of my adult life working in and around the digital world that was beginning to emerge when I first encountered Coupland. I’ve watched ideas that once seemed experimental become ordinary, and others that seemed inevitable just disappear. I’ve seen technology companies absorb the language of rebellion while becoming some of the largest and most established institutions in the world. And see the sentiment shift around them from humanistic saviors to quasi-fascist.

I so desperately want to interpret the current uncertainty as the beginning of another transformation, and to optimistically imagine that somewhere in the apparent disorder of AI there’s a new conception of work waiting to become visible.

I remember how it felt to discover the internet in 1994. How exciting it was to recognize something extraordinary in a technology whose possibilities were still mostly speculative. And how little I understood⁶ of what would follow, even though I was convinced that something important was happening.Or more precisely, how little it would have even been possible to understand!

That memory makes the present-day comparison particularly seductive. Maybe, maybe not. I can draw a line from the disaffection and malaise of the early 1990s to the entrepreneurial possibilities of the late 1990s, then draw a parallel line into the present. The resemblance is satisfying. The events seem to want to arrange themselves. It feels hard to not help it along.

And I recognize my own inclination to make the resemblance between then and now mean something.