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I’d rather know exactly what the issue is with you taking it. Either a lot at once, the timing, etc. If they are going to give a hard time every time you try to take the PTO, that is something that would tempt me to look around.
How much time? Week or so and I'd say he's out of line since everyone takes time off around the holidays. 2+ and it's kind of on you, assuming you just made the request. Mine wouldn't be thrilled about that either. You should be making these months in advance.
I’d try to have a conversation about the angst with my manager first, but yes. If this is a deal breaker for you, definitely time to start looking
Totally up to you, but I wouldn’t wanna work for a place like that!