Sorry - you are on a tractor board and your boss isn't, so I'd like to take your side... BUT...
I've made a good living fixing dysfunctional work groups. I've seen it all.
Your sending up a big red flag to me by saying you don't like to schedule your projects... AND you're wondering why you don't get your vacation time.
You have to look at yourself - not your boss. YOU have to get more type A in you.
If you want to work in a business world, you've got to adapt to it, not the other way around.
Free and loose works great when you're a creative genius, top level programmer at microsoft. But assuming that's not the case (no offense intended) you've got to embrace the power of documentation.
Have a plan.
Take some project management courses.
You'll find there are good ways to manage projects that are flexible. Get better at estimating and anticipating typical changes.
You'll see the light once you get good at it.
You're not getting your vacation time because you're not managing your time properly.
If your boss were doing your job, I'd guarantee he'd find a way to schedule his vacation time - I don't even know the guy, but I know I'm right.
Ask yourself why your boss is in his position and you're not.
If your answer is along the lines of "because he lies and he knows this or that person - and he shouldn't have the job because he's stupid" you're not a very upwardly mobile person.
If your answer is more like "he has a degree in X and is good at Y, speaks well, gives good presentations, etc..." it's more likely you're the type that will succeed in the business world.
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Today's Featured Article - Listening to Your Tractor - by Curtis Von Fange. Years ago there was a TV show about a talking car. Unless you are from another planet, physically or otherwise, I don’t think our internal combustion buddies will talk and tell us their problems. But, on the other hand, there is a secret language that our mechanical companions readily do speak. It is an interesting form of communication that involves all the senses of the listener. In this series we are going to investigate and learn the basic rudimentary skills of understanding this lingo.
... [Read Article]
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