Apple at 50: My journey to the Mac
April 1, 2026
Growing up, I hated Apple the way only an arrogant teenager could. Who in their right mind would buy an overpriced toy instead of a “real computer”? Here’s how I switched to the Mac, and haven’t looked back… despite some recent reservations.
My family’s first real computer was a 286 PC compatible that we got in 1991. Everyone around us who was geeky enough to have a computer at that time was also using PCs. I was too young then to know what the options were.
We had previously borrowed a VIC-20. I threw myself at BASIC, but quickly hit a limit. It was enough to convince my folks that I might go somewhere with this computer stuff, though. The 286 came with MS-DOS 5.0, GW-BASIC, and most importantly a hard drive. It didn’t hurt that it had a VGA card and played many excellent games.
Fast forward to 1994: my family finally gave in to my pleading for an upgrade. That summer we got a 486DX2 running at 66 MHz and loaded with 8 megabytes of RAM. I loved this machine. It ran Doom!
Around this time I started to learn more about the wider computing world. I would beg for PCWorld magazines whenever I saw them, and watched Computer Chronicles religiously. I was in awe of Sun and SGI machines. There was also this NeXT company that seemed incredible. Turns out, John Carmack used a NeXT machine to build the Doom engine!
At this time, I also learned a bit about Apple’s computers. They didn’t impress me. Real computers, you see, had a command line. The most exciting computers ran some flavour of UNIX. These Apple machines seemed like fragile toys. I flippantly dismissed them as overpriced junk for people who didn’t understand computing.
Turn forward the clock a bit further and I got access to a VAX/VMS server through my father’s school. I used a text-only version of the web for the first time, and built a “hello world” page (also text-only). I got a summer gig being a junior IT person and helped maintain a Novell NetWare cluster. I got a real job building web sites, and configured web servers running Solaris and Linux.
I didn’t really think about Apple again until a few weeks before Y2K. Steve Jobs (who I mostly knew of from next NeXT at the time) was back at Apple, and the next major version of Mac OS would be based on NeXTSTEP! At this time, I was dual-booting between Windows 98 and Linux on my work machine. Imagine being able to have Photoshop and a local terminal next to each other!
It took a bit longer, but in 2002 I bought my first Mac. It was a Power Macintosh G4 with dual 867 MHz processors and mirrored drive doors. I still think it’s one of the most beautiful objects Apple has ever built. I distinctly remember the “Switch” ad campaign being a deciding factor. The one with Gianni Jacklone spoke to me directly. The one with Ellen Feiss is still a meme.
For the first couple of weeks, I worried that I’d made a terrible mistake. The machine was gobsmackingly expensive, and Mac OS X was still very new. Yes, it ran Photoshop and Microsoft Office, but it took a while for me to find replacements for some of my Windows apps and to get a feel for the OS. David Pogue’s Mac OS X: The Missing Manual helped a lot.
But man, what an exciting time. Mac OS X felt like the platform for building the web and dealing with servers. This was just a bit before the web entered its “2.0” era. I started reading Daring Fireball just as John Gruber launched it. I followed VersionTracker and MacUpdate to learn what new OS X software was available. I found out about Panic and the great apps they continue to build. There was a real sense of community and everything felt possible.
I still love Apple’s products today, but there are new caveats. I’ve been complaining about some smaller-stakes areas where I feel like they’ve lost the plot recently. But they’ve also stopped being a plucky underdog on the brink of bankruptcy, and started being a world power making a series of terrible choices. I think their products are still the best fit for my needs, but I can’t love a megacorp the way I loved an upstart.
I’ve been rooting for Apple for just under half their existence, and I am still rooting for them. I can’t help but be excited for what happens next. Here’s hoping the next 50 years have even more of that early-2000s magic that made me switch.