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I work fully remote and have "unlimited vacation", but I have yet to test the limits of it. Earlier in April I had asked a day off 3 weeks in a row (i.e, I asked off 3 thursdays in a row) and my boss admonished me not to "let the unlimited PTO get in the way of my work", despite having only taken off maybe 6 days the entire year. When I pushed him to explain what he meant, he started walking back what he said.

Anyways I'm gonna try to ask off for 2 weeks in December, so let's see how that goes!



Yeah, that sounds pretty close to what I’ve seen — more than two weeks off starts to impinge on other team members ability to take time off (assuming you’re on a small team).




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