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To persist at a task that one is clearly not capable of.
I let this stupid n00b think he could hack me even though I'm behind a PIX, just because I wanted to watch him push shit uphill.
In Australian idiom, engaged in a hopeless task.
A: D'you reckon Davo's gonna crack it with that chick?
B: Nah mate. He's pushing shit uphill.
Taking another man up the back passage.
Derek likes pushing shit uphill