Is Generation X Our Luckiest Generation?

Why we were best positioned for the rise of our Information Age

John Blesso
6 min readJan 29, 2023

I feel lucky to have been born in 1971 because my Generation X continues to reap the benefits of simultaneously being the Oldest Young People and the Youngest Old People. Let me explain: Thirty years ago, my college class of 1993 was literally the last to graduate in which a majority of us didn’t even know what the Internet was. Just before moving to Paris (where I planned to effortlessly become an esteemed literary novelist) my older brother, Francis, said to me, “You should set up an electronic mail account. Then we could write to one another instantly on computers.”

As this was the last moment when a NERDS ONLY sign hung across the Internet, I had no idea what my supergeek brother was talking about. Soon, however, everything would change, and when I returned home in 1995 (with a completed manuscript that promptly ended up in a drawer) the United States felt feverish and barely recognizable — like a place where the parents had gone on vacation and left the teenagers permanently in charge. I sensed that I was behind the curve, for while I kept hearing terms like “AOL,” “Yahoo!” and “Chat Rooms” being bandied about, I couldn’t have explained those things any better than I could have explained a power train or a catalytic converter. I knew that I needed to catch up — but first I needed to find a job.

As I didn’t yet own a computer, I began updating my resumé (which then included my typing speed) on my Smith Corona Word Processor 2000, engaging in one of our great American pastimes: Grossly exaggerating skills and qualifications — most especially my nonexistent computer skills. For good measure, I also threw in that I was the captain of UConn’s Volleyball team, that I once escaped from Alcatraz, and that I was also a lesbian Apache.

Fortunately, I landed a job as the managing editor of The Authors Guild Bulletin. After cheerfully meeting my coworkers, I was then taken to my workstation where I sized up a computer tower standing next to a massive tube monitor. That equipment felt like a monument to the vast difference between resumé exaggerations and outright lies — lies that had now come to collect. Luckily, there was an oversupply of legal interns without enough to do, and I enlisted one of them to quietly begin teaching me how to use Windows 3.1x. All these years later I can still conjure up my fretful, over-caffeinated anxiety as I clutched a coffee mug in one hand, a mouse in the other, while he instructed me where to move the pointer, showing me how to access my local hard drive and then the office server. He was in the middle of teaching me how to move a doc off the server when he said, “Okay now put that down on your desktop.”

I set my coffee mug down on top of the desk. “Now what?”

He could have laughed a lot harder than he did before grabbing the mouse. “This is your desktop,” he said, dragging the doc off the server to copy.

Meanwhile, I still had to learn just what the fucking fuck the Internet was. After learning that Netscape was a browser while Yahoo! was a search engine, he then showed me how to compose and send my first e-mail. By the end of that nervous and exhausting first week, I felt brain-tired but like I had sufficiently caught up to my contemporaries and finally settled into that phase of a new job when you’re just sitting there, staring at your computer screen, and wondering just what the fuck you’re supposed to do.

Then, the following year, Netscape went public and my Generation X (now firmly rooted in our new role as the Oldest Young People) were still green enough to create, learn and master this new technology, leading the charge during our irrationally exuberant, tech-driven economic boom that just kept going. In early 2000, after five years at The Authors Guild (and five years of nonprofit wages) I left that terrific job to chase a higher salary as an associate editor at this boring-ass conglomerate that owned 200 trade magazines. This was right when the bubble began to inflate, when business plans scribbled on cocktail napkins generated outrageous investment capital. (I’m frequently reminded of this frenzied time as we sort through the FTX fiasco...) And it was wild to see our Boomer higher-ups — who had once written us off as “Slackers” — now literally plead with us to escort them (and all of their lugubrious 20th Century infrastructure) into our current millennium.

Ethan Hawke and Winona Ryder in “Reality Bites,” a film that fairly captured Generation X just before our Boomer overlords begged us to Sherpa all of their crap over the line into our current millennium.

Meanwhile, I still didn’t own a cell phone and have generally been a late adopter to most of the new shit. Even more so now when we can plainly see how Big Tech is running roughshod over all of us — and over all of our dopamine receptors — with their addicting products. We’re not customers — we’re “users.” This is why I’m glad to be one of the Youngest Old People, one of the last batch to have fully come of age in Analog. (We get to enjoy the benefits of the Information Age while still having the wherewithal to be wary — if we so choose — of its ongoing excesses.) I cherish my rich, non-digital childhood when I expressed my God-given right to freely run around unsupervised while wielding a hammer, bringing it down upon a D battery out in the street — just to see what’s inside.

One real downside of having come up during Analog Times — back before Everything was Everywhere All at Once — is that you got what you got. (If you had told me when I was eight that one day there would be a TV channel that only played cartoons, I would have cried.) But being made to negotiate boredom fostered invention and creativity while further instilling in us that Life doesn’t always go our way. I think it’s fair to suggest that we are objectively less spoiled, less fragile, and so less easily offended than some of the generations that came after us — none of which I’m going to name here. And I’m glad that I grew up having to make plans on the spot and then arrive on time. (And that those plans couldn’t be relentlessly changed or tweaked last-minute.) And I love that I still have two shoeboxes filled with actual letters and aerogrammes from friends.

Nevertheless, there have been other real downsides to being a Gen Xer, and perhaps none larger than our having become sexually active during the height of the AIDS crisis. We were literally fucking afraid, fearing AIDS like it was Jason gutting some slutty teen out on Silver Lake. Another is that we’ve been broadly passed over, particularly in media and politics, sandwiched as we are between the Boomers and Millennials, both of whom greatly outnumber us. I don’t mean to antagonize you Boomers, but there are just so many areas of contemporary life in which you’ve still refused to sideline your vanity and exit the damn stage. If any generation has cause to say, “OK, Boomer,” (As in, OK, Boomer, you’ve been on that ride long enough, maybe give someone else a turn?) it’s us. FOUR of our last presidents were Boomers, and that doesn’t even include Joe Biden who is older than all four of them. I’d love to see us elect just ONE Gen X president, but it seems more likely that we’ll be leapfrogged by some Millennial who’ll take possession of the Oval Office and then promptly arrange an armada of participation trophies across that desk.

One last thing: While “The Greatest Generation” will forever (and deservedly) be credited with having fought World War II, no one ever seems to remark how the people who heroically sprang to action on 9/11 (both charging up those towers and overpowering the hijackers on that plane headed for the Capitol) were overwhelmingly Gen Xers. Were we perhaps the last generation broadly raised with the value of standing for something larger than ourselves? As opposed to the self-interested, turbo-individualism that so many people brazenly wear on their sleeves today?

Just a thought.

Right now it’s a gorgeous, sunny Saturday afternoon over here in the Hudson Valley and really just a perfect day for a sunset hike up Mount Beacon before running back down. Yes, I’m literally going to go run around outside, something that I actively chose to do back when I was just a kid. You know — once the credits rolled on The Bugs Bunny & Roadrunner Show.

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John Blesso

John Blesso is a writer, performer and builder fascinated by food, politics, and our collective refusal to stop doing crazy dumb shit. He lives in Beacon, NY.