June 2, 2026
Finding Nostalgia in a Windows 95 CD
Found a stack of Windows 95 disks in an IT closet today. Couldn't throw them out. Here's why.
I found a stack of Windows 95 installation disks while cleaning out an IT closet at work today, and I couldn’t quite bring myself to throw them all out. So I’ve had one sitting on my desk for half the day, making me smirk every time I look at it.
It’s completely worthless. You can download Windows 95 from some random corner of the internet without much effort. Yet I held onto it like it’s some unearthed piece of antiquity.
Isn’t it interesting how we associate memories or feelings with things?
When I look at this CD, I think back to that old Windows 95 startup sound - the one I’d panic about going off because I was sneaking onto the computer and my Mom had left the volume on max. It brings back memories of Yahoo! Pager (yes, I’m old), ICQ, and IRC. Spending late nights in Yahoo! Chat rooms talking about Star Wars or playing trivia games with people from all over the country - or even the world.
The internet was so raw and untamed back then. Maybe it’s nostalgia speaking, but it felt like we were experiencing something grand. Finding cool new websites, clicking through a Webring that kept you jumping from Boba Fett fan pages into the late hours of dawn. Yes, dawn. Heh.
Then there were MUDs - basically Dungeons & Dragons meets chat rooms. Fully text-based RPG games, online, before that was really a thing. An early precursor to games like Lineage or eventually World of Warcraft. The internet was new, crazy, and unprotected, and every day was an adventure exploring it. Sometimes to my detriment. I’ve seen things.
Today’s internet feels highly curated. We’ve lost a lot of that organic community, and when you do find it, it’s often an echo chamber. Ads were there back then too, but they weren’t so aggressively targeted. There wasn’t the constant political, societal, or data-privacy anxiety about how much information is being collected and where it’s going.
It was freedom, as silly as that sounds.
So maybe I’ll keep this silly CD on my desk for a while. It takes me back. Can’t say I mind it.
What’s your favorite memory of the early internet? Join the discussion on LinkedIn.