Instead of just dumping the first thought that comes through your head on us, could you explain why you think it wouldn't work? What issues do you see arising?

It seems to me we go through life with little exceptional circumstances all the time, and go right back to normal pretty easily.

Is it that hard to imagine having a holiday not disrupting the weekly rhythm of your life? For example, there's a group I go to every Wednesday. But since Christmas and New Year's are both Wednesdays, it's being skipped two weeks in a row. On the other hand, if Christmas and New Year's "didn't count" then we could carry on without changing the schedule, getting in the way of other standing plans, etc.

Because that's all I've got and I haven't really given it much more thought than my initial gut reaction. It just seems infinitely bizarre not to have a weekday, and writing about it now seems like it would make synchronizing and automation hell with a day like that.

There's more to life than synchronizing and automation.

That's the least warranted, holier than though sentence I've ever read here on HN. I don't even know where to begin to pick this apart. It's not about enabling automation in the factory making sense, it's about keeping order in our minds and in our software...and having an "oopsie" blank day with no way to logically derive will do more to fuck with your intuition about time and calendars than having everything else around it neatly fit. Even something as simple as counting days on your hands will become wholly unintuitive because you now have to consider something worse than an edge-case.

But go ahead, make this about how narrow-minded my view on life is. Arguments like this are why wishy-washy calendar ideas like the one being proposed got blown to bits and relegated to a single page wikipedia article barely worth the occasional mention.

Come on, I don't disagree with you. But when I was a kid and I first found out about calendar proposals with blank days it all seemed magical to me and it just seems weird to me (with regard to this topic) to think about practicalities.

How on earth is it impossible to logically derive a Leap Day every four years in a consistent spot, especially compared to any other calendaring we already do?

Simple - they don't have a weekday :)

Every once in a while there would be a day called Leap Day.