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For me experience will almost always trump theory. It certainly depends on the job but the Jack of all trades, in most circumstances, will be money well spent.
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That definitely depends on the subject -- construction, I'd def. take the experienced one.
I can't imagine a field that I would hire a book educated over a jack of all trades. The Jack of all trades gets my vote!
Jack will always win! But don't drop out just because I said that!
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