Gen Xfest: the Quiet Desperation of a Soon to be Forgotten Generation

The title is probably overstating things, but I couldn’t resist. At a certain age, you start to notice that the events shaping the tech industry don’t feel new so much as rhymed. Not because tech or capitalism or anything else is inevitable, but because at scale we seem to fall into the same grooves over and over again.

In my twenty-odd years in tech, I’ve watched the same warning lights flash with almost comic reliability. The particulars change (web 2.0, blockchain, crypto, and now AI), but the pattern doesn’t. Someone—usually early—points out the risks: this will concentrate power; this will marginalize huge swaths of the population; this is ripe for abuse; this will move faster than our ability to manage it. The alarms are clear, well-articulated, and widely shared.

And we do it anyway.

Not blindly, and not even reluctantly. We do it eyes wide open, buoyed as much by the promise of growth curves as by the fear of what we stand to lose by not getting in early—preferably as the one doing the taking. There’s a shared belief undergirding everything: that the trade-offs will be manageable, or at least someone else’s problem. “Danger, Will Robinson” isn’t ignored so much as acknowledged and then promptly de-prioritized.

That’s the part that’s been hard to shake after my first two days at Cloudfest—or what I’m affectionately calling Gen Xfest. It’s not that we fail to see the signposts; they’re everywhere, practically screaming. It’s that we’ve chosen to surround ourselves with environments that make them easier to ignore. The conference is set inside a kind of off-brand Disneyworld, a place built on curated reality and cheerful illusion, where everything is “frictionless” (a term repeated like a mantra in sessions) and consequences are politely kept just out of frame.*

And maybe that’s the point. It’s not that we can’t see the warnings. It’s that we’ve learned how to live with them—absorbed them, normalized them, priced them in. We didn’t learn much from 2008; we adapted to it. And here we are again, crowding the trough, feeding with the same urgency, telling ourselves the same stories—right up until the system decides it’s time to retire us.

I think that’s where the “Gen Xfest” line comes in—and it’s not even mine. During the pre-conference day for WordPress agencies, emcee Raquel Manriquez was doing everything she could to breathe some life into a fairly moribund crowd. The Germans, in particular, were not especially receptive to the American pep rally approach.

But she was sharp, perceptive, and genuinely funny. One of her jokes, riffing on the average age of attendees (mid-40s to late-50s), was that the conference should really be called “Gen Xfest.” It landed because it was true, and it also connected a few dots for me.

A lot of the WordPress agency folks in the room were, quietly, freaking out. More than a few presenters were cocky and occasionally tone-deaf while confidently declaring that programming was no longer a viable market, that AI was already driving prices toward zero. You could feel the floor drop out from under people.

AI wasn’t being discussed so much as wielded like a bat swung from session to session, seeing how many agency owners it could knock off balance. And yet the refrain was familiar: stay curious, adapt, this is just the next industrial revolution. Third, fourth—who’s counting.

It didn’t land. Because beneath it you could feel something else: not excitement, but recognition. A sense of professional (and maybe personal) exposure. The same pattern, again, just wearing a new skin.

The punchline came in a session I attended towards the end of the day:

It’s worth remembering that no one has figured out AI pricing yet.

Which is… something. We’re being told, over and over, that the cost of software development is racing toward zero. And maybe it is. But the cost of AI? That’s still being heavily underwritten by investment capital. The buffet is open, the plates are full, and everyone’s pretending this is the new normal.

It’s not. It’s just the latest version of the same trade-off: scale now, price it later, and hope you’re not the one left holding what promises to be yet another enormous bill.

The uncomfortable part is that I’m sitting there very much a part of the problem. I’m worrying about my business, nervously preparing to send my kid off to college, trying to piece together some kind of future I can retire in while all of these economic, geopolitical, and technical forces churn around me. I’ve been through some of this before, and I can’t say I’ve learned much—much like the culture at large.

I’m running alongside everyone else toward the same cliff.

I just happen to know it’s there. I’m not sure that’s growth—maybe just honesty?

*Europeworld is a total trip. It recreates simulacra of its own monuments—places people could just go and see for themselves—yet everything is miniaturized, contained, and inward-facing. It’s hard not to see a parallel with the conference itself, especially as re-entrenched nationalism (and the business opportunities that follow) gets repackaged as “digital sovereignty.”