Y2K is especially interesting because the fact that the year 2000 would one day occur was entirely foreseeable, and no less probable in 1990 than in 1999. I can hardly think of anything with closer to 100% probability of happening.

To be fair, there was a non-zero chance that society could have ended (or your company, or the tech became obsolete) before 2000, which would be higher the earlier before 2000 you were.

The tech being obsolete is why Y2K was a smaller problem than it would have been otherwise. Most places were no longer running much COBOL code. But banks are famously slow to upgrade their tech, and for good reason much of the time, so most of the world's remaining COBOL code (and other code too, COBOL is just what I'm most familiar with, not that I'm all that familiar with it) was in banks and other financial institutions.

Year 2038 says hi.