Boss: How long will it take to finish the project?

Me: (Gives date for finishing dev and deployment.)

Boss: great, sound reasonable.

Me: ...

Boss: wait. Aren't you on vacation the two weeks after that.

Me: jup.

Boss: yeah we are not doing that again. Client can wait another two weeks.

Before someone says no Boss/PM is like that, he was/is a developer too so discussing deadlines and efforts is usually pretty relaxed since he knows our codebase and how long it takes to do things.

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    As much flak as I give my bosses, I’ve never had one that would say you can’t go on your already scheduled time off due to a client deadline. It’s your time off, you earned it, they can find someone to fill in or wait.
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    @EstrnAdventures Same here, thats why he said we will just wait with deployment until I am back. Last year a chain of unfortunate events and a deadline set by our clients client resulted in a situation were I had to make a hotfix during my vacation. This time we are just replacing an old API with a new one. There is no real deadline since the old API is working fine. It just became an unmaintainable mess over the years.
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