I think if we reach that point, we would probably look at the Earth calendars the same way we currently look at the Latin language.
Please don't do a tech reinvent / reimagine of calendars to exactly how they are now but with ads and a monthly charge.
Other than that, I don't think Gregorian calendars are going anywhere. Traditions have a way of overstaying their welcome, especially once they are automated.
If you don't pay, you will not get the new day.
It'll be crept in through a Total Recall style augmented sleep where a week long holiday seems teally only takes a night's sleep.
When normalised, leisure time will becme a subscription service.
incomingpain•8h ago
Next century, so not near future, the leap seconds and leap days will break everything forcing a major calendar reform.