Digital Déjà Vu: From Dot-Com to AI, A Designer’s Tale of Two Revolutions

History Echoes

Remember those wide-eyed print designers of '99, clutching their well-worn copies of Photoshop, staring bewildered at their first HTML editor? They were artists in a familiar medium suddenly asked to paint with light and code. Their precious picas and crop marks were being replaced by mysterious concepts like "viewport width" and "cascading styles."

Sound familiar?

Here I am, a design leader in 2025, watching history rhyme. Back then, we struggled to explain to clients why a website couldn't be an exact replica of their brochure. Today, I'm having eerily similar conversations about why AI interfaces can't be as predictable as traditional apps. The parallels are uncanny: In '99, we debated whether every business really needed a website; now we debate whether every product really needs AI. We once agonized over whether to organize our teams by print versus web; today, it's traditional UI versus AI interaction design.

The Familiar Sound of Uncertainty

The whispers in design leadership circles echo those of the dot-com era with stunning similarity: "How do we hire for skills that don't exist yet?" (Remember hunting for that rare unicorn who knew both print and HTML?) "What does an AI design team structure look like?" (Just like we once wondered how to structure web design teams.) "How do we balance innovation with reliability?" (The same question we asked when deciding between Flash or HTML.)

And of course, designing for AI in its infancy has its usability challenges for designers to help work out the kinks. I think this is well explained by usability pioneer Jakob Nielson: “ChatGPT is just like one long scrolling list, with no option to point or click on the bits you want to change; you have to describe what you want to change in another paragraph. This is history repeating itself, because when the web first came out, all the things we knew about good design went out the window.”

Meanwhile, venture capital flows like champagne at a Silicon Valley launch party, and every startup adds "AI-powered" to their pitch deck, just as they once crammed ".com" into their names. Even the job titles feel familiar – replace "Webmaster" with "AI Design Lead" and you'll know exactly what I mean.

And yes, the bubble might pop. Some AI startups will vanish like pets.com and its sock puppet mascot. The hype will settle, valuations will normalize, and some will declare "AI winter is coming." But they'll be as wrong as those who thought the internet was "just a fad" after the dot-com crash.

Leading Through Change

Because here's the thing: Those design leaders who embraced the web, who helped their teams think in links and flows instead of pages and spreads? They didn't just survive – they helped shape the digital world we live in today. They guided their organizations through table-based layouts and Flash intros to pioneer responsive design and dynamic content systems. Some of the best digital designers I know started as print designers who were brave enough to learn HTML when others dismissed it as a passing trend.

Now it's our turn. We're not just designers but design leaders pioneering human-AI interaction, sketching the first maps of this new territory while bringing our teams along on the journey. Every prompt pattern we craft, every AI interface we design, every failure we learn from – it's all groundwork for what's coming. And unlike those early web design leaders, we're not just building static websites; we're creating dynamic systems that think, learn, and grow.

I can't help but feel a surge of excitement every time I meet with my team to tackle new challenges. Each day brings opportunities to mentor designers through uncharted territory, to establish new best practices, and to shape how humans and machines will interact for decades to come. Sure, our prototypes might look as quaint in 20 years as those first websites do today. But that's exactly why I love this moment – we're writing the first chapters of a story that will transform design forever, and we're doing it together.

The Dance Begins

The machines are ready to dance, just as the internet was ready to grow. Time to choreograph some new steps.

And you know what? I couldn't be more thrilled to be here, right now, at this inflection point. Every morning I wake up eager to dive deeper into AI design with my team, to experiment with new interaction patterns, to fail fast and learn faster together. This isn't just another tool in our design toolkit – it's a fundamental shift in how humans and computers interact, just as seismic as the shift from print to web. And I get to be part of shaping that future while helping other designers find their footing in this new landscape. How incredible is that?

Let's embrace the chaos, learn the new language of AI design, and create experiences that would have seemed like science fiction just a few years ago. After all, in 1999, the idea of carrying the entire internet in your pocket seemed pretty far-fetched too. The canvas is infinite, the possibilities endless, and my team and I are just getting started.

Top image by Milad Fakurian