Back in 2008, I wrote a post called Should It All Be Miscellaneous? inspired by David Weinberger’s book and the liberating idea that the web didn’t need rigid hierarchies. Tags, links, and search could replace the old drawers and filing cabinets of the physical world. At the time, that felt like progress, why force everything into neat boxes when the web could be sprawling, searchable, and serendipitous?

Why do I bring up a blog post from nearly 20 years ago? I have a new habit of finding a spot on Saturday early afternoon to catch up on work and have lunch. I was standing in line yesterday and I remembered that post and wanted to reflect on how that compared to what we are discovering in our AI journey. The comment section proved worth the rabbit hole.

So here we are in 2025, and I find myself revisiting that question in light of what I wrote recently in Exposing the Missing Pieces in Our Content. Not so much what I wrote, but what the community gave back in the comments. The irony? The very thing that once felt like freedom, letting everything be miscellaneous, has become one of our biggest challenges.

AI has thrown a harsh light on this reality. As Mario said in the comments, “One of the main blockers to unlocking the power of AI is the state of our data and information.” That’s the truth. Our Copilot trainings have surfaced the same theme over and over, the technology is ready, but our content isn’t. Thousands of sites, all managed differently, with redundant information, and with varying levels of accuracy and oversight. It’s not that the web is broken, it’s that our relationship with it hasn’t matured.

I guess that makes some sense, the web as we know it is still relatively a puppy within the higher education governance timeline. Let’s be honest, IT governance is still a work in progress, and it predates the web on our campuses by 30 or so years. Maybe it is no wonder we are still looking for answers?

Cody’s comment stuck with me too: “I don’t think websites are going anywhere.” I agree (even though I poked at him). Websites aren’t disappearing tomorrow. But the way people expect to interact with information is shifting fast. AI agents, chat interfaces, and voice assistants aren’t replacing the web, they’re reframing it. They’re forcing us to ask what is the role of a website when an agent can synthesize answers in seconds? Maybe the answer is harmony, as Cody suggested, agents and websites complementing each other, each doing what they do best.

Valerie and Kristin added another layer: this isn’t just about technology; it’s about stewardship. Kristin’s metaphor hit home: “We don’t build a world-class art museum and ask everyone to drop off the paintings they like most.” Yet that’s how we’ve treated our institutional web for decades, every department spinning up a site, every reorg leaving behind digital fossils. AI is exposing that fragility. And as Kristin said, maybe the CIO has to become the Chief Curator now. I mean content is information after all.

So here we are, nearly 20 years after I asked if everything should be miscellaneous. The answer? It depends. The web still needs flexibility, creativity, and openness. But it also needs anchors, places where truth lives, where information is accurate, current, and trusted. Not because AI demands it (though it does), but because our community deserves it.

AI didn’t create this problem, it is revealing it. And maybe that’s the push we need to finally treat our information more like core infrastructure. Why would that change the equation? IT governance has given us the idea of investing wisely over the lifecycle of systems to ensure they are resilient, robust, and reliable as they are constantly consumed. Yes, the content floats on physical infrastructure, but shouldn’t we value it as much as the switches, cabling, and access points? And just like with managing the lifecycle of infrastructure, it should be governed by the most critical, highest risk, and greatest value creating investments.

It all begs me to ask so many questions that I don’t have answers to. Questions like, if we could only invest in 20–30 primary sites across the university, which ones would make the cut? How do we balance the creative chaos of the open web with the need for authoritative sources that AI (and humans) can trust? Are we ready to think of ourselves not just as technologists or communicators, but as curators of institutional knowledge?

I bet someone out there has a thought or two.