Tech Used To Be Magical. Why Isn’t It Anymore?

I’ve been pondering something for a while now, but have held off “thinking out loud” about it because I was worried I might sound like a guy yelling at the kids to get off his lawn. But f*ck it, this is my site, and I think it’s time to air this one out: Technology isn’t delivering on the magic anymore. Instead, it feels like a burden, or worse.

For decades, digital technology delivered magical moments with a regularity that inspired evangelical devotion. For me, the very first of these moments came while using a Macintosh in 1984. Worlds opened up as that cursor tracked my hand’s manipulation of the mouse. Apple’s graphical user interface – later mimicked by Microsoft – was astonishing, captivating, and open ended. I was a kid in college, but I knew culture, business, and society would never be the same once entrepreneurs, hackers, and dreamers starting building on Apple’s innovations.

And build they did. From that point onward, the magic continued, sometimes in massive leaps (like the Mac itself), sometimes in smaller ways that built upon those leaps. One such example was my first interaction with desktop publishing software, in 1987. Learning how to work with that software turned me from college hack to professional media creator, and I never looked back. What I didn’t imagine was what the tech industry would do to the media world I was so eager to be a part of – but that disruption was still decades away.

My first login at the WELL, an early online service, was another such milestone of the late 1980s. Staying up late talking about random Grateful Dead shows with people based all over the world made me realize how powerful “social networks” were going to be. I almost felt like I was getting away with something – like I had a secret shared only by a few thousand others. I imagined a day when services like the WELL would sport robust graphical user interfaces and unlimited bandwidth. But again, what I didn’t imagine was the centralized, algorithmically driven models of Facebook, Instagram, and TikTok.  The WELL – a command driven, text-based service – was social media at its best, a funny thing to reflect on given all that’s come since.

Then there was the web.  Those of you who came of age after the web became commonplace can’t imagine how mind-bending it was to be one of the first people on earth to load a web page and jump from link to link. In 1993 I downloaded an early version of the Mosaic browser and began a lifelong journey. But back then, most of the sites were earnest, information rich, amateur, and just plain fun. Yes, the early web got super crowded, super fast, but that’s when another piece of magic broke through – Google.

Google in 1998 was a magic machine equivalent to the Mac in 1984. You put in your question and *boom* – nine times out of ten you ended up where you wanted to be. It was captivating, liberating, and incredibly useful. It also sparked the rise of the independent web – an early (and mostly lost) version of the internet that was driven, for a few years, by a relatively pure signal called backlinks.  Which leads to the tech’s next magic moment….

Blogs. I know, just typing that word kind of makes me cringe, because I’ve always hated the term. But from about 2001 to 2008, weblogs formed a truly magical ecosystem where respectful debate and true conversation took place. Blogs formed the spine of the Internet itself, giving shape and substance to Google’s growing index (and dominance).

Tech offered some non-internet related magic as well. If you’ve never used a Tivo, then you unfortunately missed out on television’s most singular moment of product-market fit. From 1999 until the mid 2000s, Tivo worked like a blanket digital recording device that swallowed all of cable television and re-ordered it in a way that you, the consumer, controlled completely. You could record whatever you wanted, time-shift your viewing habits, and skip the ads with a few clicks of your thumb. It completely changed what I expected from television – and since Tivo’s demise, my TV viewing experience has only gotten worse, despite moving almost entirely to streaming. The reasons for this are myriad, but in essence they come down to this: The television industry didn’t want Tivo to dis-intermediate its relationship with consumers. Funny what happened instead: Apple, Google, Amazon and Netflix stepped in and did it anyways – and far less well.

Tivo makes me think of another brief moment of tech-driven magic: Early Spotify. It might be hard to imagine now, but in 2008, when Spotify launched, most music fans had large collections of compact discs – CDs – and most computers had CD-ROM drives. That meant you could take your entire music collection and rip it to your computer, then upload it to Spotify, which offered a robust interface for managing and playing your music. I used to buy new music on Amazon, tear open the box, toss the CD into my Mac, rip it to Spotify, and listen to my new tunes over and over. It was just like buying a new album, but the digital interface gave me new superpowers like playing music on my computer, searching through music based on keywords and playlists, creating “mixtapes” on the fly, and much more.

There are many, many more such moments – Skype, the first Kindles, early usenet, hell, even early Facebook, early Snap, and the first iPhone – but I’m going to stop now and think out loud a bit about all of this. What all these moments of tech magic have in common is the power and control they gave to the average person. Early tech gave us agency over parts of our lives that were previously hobbled by physics and economics. The Mac gave computers a physical interface. Desktop publishing allowed us to leap over the physical and economic limitations of the printing press. Early online services, then the web itself erased boundaries of geography, information access, and culture. Google, for a brief and wonderful period, helped it all make sense. Services like Tivo and Spotify gave us agency and elasticity over media.

But..I no longer feel like Google, or the web, or television, or Spotify are in anyway magical. In fact, they all kind of suck now. Why? Yes yes, the ad model and surveillance capitalism, but honestly, I think it comes down to our society’s cardinal sin of favoring convenience over agency. Turns out it’s just easier to let Spotify or Netflix or Instagram feed us media that, while perhaps not our first choice, seems consistent with things we’d likely choose if we actually decided to make a choice in the first place. The magic that we felt when tech was young has been replaced by the dark art of the hidden and inscrutable algorithms busily feeding us stuff we never would have thought of engaging with otherwise.

I fear this model – where our own agency has been sacrificed at the altar of convenience – will serve us poorly should artificial intelligence become the next framework for how we engage with computing going forward. And there’s no doubt that Nearly Everyone In Tech wants generative AI to be The Next Big Thing, proof that tech can, in fact, bring back the ol’ magic of yore. I’ll expand on this idea more in future posts, but in short: If we don’t take our agency back when it comes to “the agentic web,” I fear this entire AI revolution will come to naught. And we’ll have wasted billions – and a helluva a lot of our collective time – in the pursuit of it.