User blog comment:Katat0nyx/Determinging the difficulty of contractors/@comment-5261432-20130421140559/@comment-5180808-20130604232137

I think by "get ahead" he means sending extra trains that aren't needed by any current contract, so that you can build something instantly once you complete the earlier contract that blocks it. This becomes a useful strategy if you've got lots of international slots and not many contractors to complete (so you'd otherwise be leaving the international slots empty or sending trains to friends only).