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I never broke through, and it wasn't for lack of trying. I think the easiest way is to get employed at the low level accounting, marketing, or similar, put in 7,8, 10 years or whatever, then make a move for project lead, management, HR, etc.
I had similar trouble: too much retail experience and a choppy school record. I had to go blue collar in the end; too squirrelly for middlle class white collar.