May you have peace!
Problem is... your boss doesn't know how to be a "good" boss. Most "middle management" bosses don't. Most of them think that such knowledge is instinctive... that they automatically morph into a "good" boss just because they've been promoted/got the job. Nothing could be further from the truth. Most of them get the job because those with brains won't take it. And most of them... don't have a clue as to how to supervise. They hand out orders willy-nilly that they themselves wouldn't ever be able to follow.
So, how do you handle it? You've got options:
FIRST OPTION: Talk with your boss. Not TO your boss... or about your boss... but WITH your boss. You go to him and say something like:
"I totally understand that you want me to take more initiative, but I'm not sure what that means to you. For me, it means..."
and then tell him what it means to you. Then say:
"But I'm not sure it means the same thing to you because when I... you responded... and that made me think that perhaps we're not on the same page. Am I missing something? I'd really like to do this the way YOU need me to, so any input from you would be really appreciated."
Then... listen. Don't assume what he's going to say. And don't take anything he says personally (especially if he's really a jerk - in that case, you're no one special to him and he'd probably respond to anyone the same way).
LISTENING may require (1) that you remain silent until he has finished, even if you're chomping at the bit to say something; (2) that you don't indicate (with your body language) that you know what he's "going to" say... even if you already know; (3) that you don't anticipate what he's going to say... if you don't know; and (4) that you "reflect back" what you believe he's saying (for example, "Okay, what I hear you saying is..." and then ask "Is that correct?"
And then LISTEN again. Let HIM tell you what he wants, specifically.
If you do this, one of two things will happen: either he'll get more specific and clarify what he needs and is looking for OR he'll realize you're smarter than he thought you were (and, most probably, smarter than him!)... and get off your back. Either way, you win.
The ONLY way you'll lose is if he's an anal retentive blow-hard, who really doesn't give a hoot how his deficient supervisory skills are affecting his subordinates. In that case, my advice would be to consider the SECOND OPTION:
Put in for a transfer... or change jobs. Because bosses like him don't change.
I bid you the greatest of love and peace.
Your servant and a slave of Christ,
SA