Wrong slang. It's supposed to be "I couldn't care less" - because I have no interest. "I could care less" means there is some interest.
"Leaving? I couldn't care less."
Making your way with just what you have on you - out of what's in your pocket. Being without one's usually available resources.
It's always used ambiguously - which is why everyone's forgotten what it means. "I'm out of pocket" or "He's out of pocket for awhile".
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