The end of the year was filled with an extended series of video gaming sessions when Jim was available, and comic-book reading when he wasn’t, with a foundation of loud music playing on my stereo and a general freaking out over being unable to do the job for which I’d been hired.

Also, depending on who you believed, there was a non-zero chance that the world as we knew it might end. It would end, of course, as worlds are prone to do, but we had some time yet.

Still, while most security people were telling me that critical infrastructure had been thoroughly assessed and all possible instances of what was called the Y2K Bug had been assessed for their risk and everything looked fine, as far as anyone knew, the fact remained that this was still only as far as anyone knew. As I’d find out in my adventures to come, there were a whole lot of old systems out there, and some of them were stuck in closets where an entire generation of staffers had passed by every day without ever once logging into them. Crossing over to the year 2000, and rolling over all the digital calendars from 1999 to 2000 was anxious-making for people who knew what shortcuts computer programmers tend to take, especially those from decades back when you were starving for bytes, and the difference between “1982” and just “82” could make a serious difference to the amount of data you could hold in memory at one time. Some people wanted the extra data and performance and figured that their apps surely wouldn’t still be running in 18 years, so they didn’t bother logging the whole year, just the two left numbers.

The fear was over what would happen when the year in a two-digit calendar suddenly rolled over, like a 1980s video game score, going from 99 to 00. Computers had not famously behaved smoothly when faced with unexpected inputs — especially memory-poor systems, which were least likely to have cluttered up their code with tedious things like checking the format of every input and planning out reasonable responses to error conditions. The practice of building and managing computers had been a regular roll of the dice for many years, to some extent, so it wasn’t like this had been computing’s first chance to screw up a civilization. But it was computing’s first big, “The World Is Watching” kind of test as a critical infrastructure.

The Internet had been designed in the paranoia of the Cold War, where you had to design around an arbitrary chunk of your country simply disappearing in a rush of thermonuclear holocaust, so the network itself didn’t seem to be a worry for most people. People like Jim had no concerns about Yahoo’s ability to stay online come January 1st of the year 2000. It was the old and unnoticed box in the closet at a power switching station, or at a fuel processing plant, that kept people up at night.

The East Coast long-distance phone system outage in January of 1990 was never fully explained — we know the mechanism, but we still only have suppositions as to what kicked it off. We only know that some unexpected inputs crashed half a nation’s worth of computing infrastructure. As relatively minor as that had been, it had led directly led to the Hacker Crackdown, and while it’s possible that it could’ve been a hacker messing around with a switch that caused the cascade of failure, it could’ve just as easily have been a flood of traffic and an unexpected crash-level error condition that hadn’t been anticipated. Even in the heart of Silicon Valley there were “Y2K Disaster Supply” stores, where people were clearly stocking up on prepackaged meals and camping supplies, hedging any bets against apocalypse.

On New Year’s Eve, 1999, I hung out with the Kroll accountant and some friends of hers. She was three years older than I was, and intimidatingly attractive. I had a crush on her as deep as the ocean, but I was too afraid for my professional life to have room for a relationship. I figured I could lose my job soon, and if I was going to spend time with someone I’d rather it be for the long term. So when she stood and said, “Let’s go outside,” and we all stared up into the clear starry sky, holding our breaths as the clock changed over — listening; no explosions, only distant cheers in the night — I did not try to hold her hand because I could only embrace so many fears at the same time. They were like pins, pressing me back against cool black velvet.

But even though our president had the military on high alert, calling up the National Guard and sending choppers cross-crossing states, it would still be a little while longer before the end of the world.