In an office where overworking is a badge of honor — if not a competitive sport — a request for vacation can be daunting, even if vacation time is part of your compensation package. The worry is not so much the request itself, but feeling judged for making it. What if your manager makes it seem like you’re not a team player? Not quite as committed to your work as you could be? Not as ambitious as others are? And what if she says no?