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.
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Year 2038 says hi.