Oh, I’ve got a good one about this.
Back in 2000, I was living in a new city, and cold-calling graphic design firms. At the time, most of the web looked like utter ass, and my feeling was that it made more sense to try to be the in-house developer for designers, rather than try to bring design to web development firms.
So I put together a resume with my personal URL placed prominently across the top, and knocked on the door of every graphic design firm in Portland. I met a bunch of confused designers, and didn’t get a single call or email back. I noticed in passing — and importantly to this story — that the whole industry was still wedded to Macs running the non-memory-protected OS 8. Months passed and my savings trickled away.
Eventually out of desperation I took a job at a shipping company that was rewriting their in-house software suite. I noticed that they had a couple dusty Macs in the corner for browser testing that they never bothered doing, and thought it might be amusing to see how my site loaded.
It turned out that there was an error in the CSS engine in MSIE Mac that crashed the system. Not the browser, the entire computer. Click, smash. I realized with horror that I had spent months crashing the computers — along with the unsaved work — of every graphic designer in Portland.