Where did the web’s personality go?

4 min read
Jake Underwood
  •  Aug 13, 2019
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In May, “You’re the Man Now, Dog!” a long-running meme site first created in the early 2000s, shut down unexpectedly. The eulogies flowed as another influential, beloved internet site was taken offline. As my Twitter timeline grieved, I realized that I had a lot to learn.

I’m 23. The start of my internet life coincided with the launch of the iPhone in 2007, a time when what the internet was and could be radically shifted as we rethought the web’s place in our lives. Suddenly, the web became as diverse as ever–and then monotonous. 

I’m sure you’ve felt it, too. The flattening of logos (need some references? Check out Humans of Flat Design on Twitter). The shift to minimalism. The reduction of customization on social profiles. When the internet grew, we saw web design—once a unique place for creativity, personality, character, and (yes) all the ugly, hideous amazing designs that spawned—trend toward the professional. By the time I was of age to freely browse, I had missed what had made the internet so fun.

And as I learn about the internet’s relics and the people who miss them, I’ve started to ask questions: where did the web’s old personality go? Why did it leave? And how do we get it back?

Did I miss out?

The wild west of the 2000s internet

“It felt like the Wild West. No one really knew what they were doing,” says Jason Kottke, who may be the last man standing in the blogosphere.

Jason Kottke is internet and web design royalty, and for good reason: his blog,, was one of the internet’s first in 1998. 

“In the beginning, you had a lot of people who weren’t designers,” Kottke explained. Instead, the majority of the internet’s early users just had a general interest in computers and may have known enough to do some basic programming work. The resulting products were useful, but ultimately simple.

It’s certainly not pretty, folks, but it has a retro energy we’re all into again.

Sure, Lana Del Rey’s early Myspace profile could use some more modern design ideas. But look at the customization options!

When I go look at some of the web’s most popular sites from the early 2000s–and even into later in the decade–I envy those who were able to experience them for the first time. Participants were–as Kottke phrased it multiple times–“figuring it out,” leading to a community that made breakthroughs and shared information at breakneck speeds. 

Sites like Homestar Runner and Albino Blacksheep could have been bonding points for my group of friends growing up. Instead, they were just before my time. And while I got to experience the tail end of services like StumbleUpon, I was too late to let the site shape my internet use (now, founder Garrett Camp is best known for co-founding Uber, in case it wasn’t indicative already of where the web has gone).

Oh look children, a classic example of the two-column blog!

As I walked backwards through the chronology of the web, I realized that it was at the turn of the century when the professionalization of the web began in earnest. And that, in turn, led to an explosion of weird.

In the Dot Com Bubble era, companies developed websites for their newly founded internet companies selling anything from software to kids’ toys to CDs. What was once a tool for futurists became a mainstream product, and people flocked to check out what the web could do.

From the good old days when people still bought music.

With a new surge of users, unique ideas flourished. Social media sites like Friendster and Myspace allowed us to customize our profiles to showcase who we truly were –or, at least, who we wanted to be (and if you speak to many of today’s design leaders, they trace their interest in design to tweaking that Myspace of Geocities profile).

Blogs became more common, enabling clever, funny, or insightful voices previously unheard from. And digital innovators developed their own sites to host animations, games, simulations, or other never-before-seen content that was entertaining, helpful, or simply wacky. As a result, you get “You’re the Man Now, Dog!”.

The classic YTMND: The Picard Song. Headphones up loud!

In many ways, the web once again became the Wild West. Users were free to create whatever they felt was important, and it had the potential to spread across the web. 

This kind of rapid change in what the internet can offer is mostly gone, and it’s sad to have missed out on it. Rather than knowing the same five apps and sites I’ll visit every day, the web of old was more likely to surprise and delight. The creativity is there, I guess. But it’s stuck on the same handful of websites.

Take a minute to reflect on your internet usage now and it becomes apparent that things have radically changed again. Twitter, Reddit, YouTube, back to Twitter, a quick Slack message, and a stretch of Netflix. To be online is different than it’s ever been, and there exists a form of sameness that appears to be much different than in the internet’s youth. 

But if the early Dot Com boom led to the weirdness, is today professional web ripe to be upended again? Will all of our flat illustrations and shades of blue lead to the 2020s equivalent of overlapping gifs with bad midi files?

The future will not look like the past

When news website The Outline launched in late 2016, its design was an immediate differentiator; the Wall Street Journalcalled it “highly visual and graphics-rich,” which hardly does the site’s hodgepodge of squiggly animations, brash typography, and large images justice.

The Outline was widely praised and criticized for the design. Senior designer Jack Koloskus said we’ve since changed our tune.

“Where years ago being confronted with a design that was harder to understand would prove unnavigable for an average user, now it might still present a small challenge, but it’s something you can find your way through,” said Koloskus. “I’ve always found design that’s slightly challenging to be more rewarding to experience in the end.”

In the late 2000s and early 2010s, Koloskus said the web established a set of standard rules to make websites easier to use and navigate. Since then, we’ve evolved, grown in our abilities, and become more capable internet users, allowing for increased freedom.

These standardizations have come from multiple different sources, spearheaded largely by the World Wide Web Consortium and the Web Standards Project. The point of these rules is to not only make the web more usable and appealing to the eye, but also more accessible to users with disabilities. 

Projects like these have enabled is a whole new set of users to more efficiently use the web. Moreover, they’ve also shown how the web can stay unique while also accommodating as many people as possible.

“People using the internet have naturally evolved a lot, and I think users are changing faster than design is,” mused Koloskus. “The very functional, very straight-forward design is all over the internet for that reason, but just because it’s ubiquitous doesn’t mean it’s the only correct way to do things.”

Koloskus is implying a sort of optimism, putting our web society further along the timeline than we might give ourselves credit for. The sites we visit are simple and familiar because they had to be to accommodate the world growing into the internet. Now that we’ve become masters of the tool, it creates opportunities for the web to get strange again.

Kottke is equally optimistic: “People will get tired of what’s going on right now,” he stated. “If it feels like web design is stuck, maybe in two years that won’t be the case. You think society has painted itself into a corner, and then it finds a door.”

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