I belive that this is some archaic old saying suggesing that the person who this is being suggested to try really hard or something. May have to with college sports. I don't know about you, but when I hear this, this phrase conjures up images of getting piss drunk and staggering home, yet passing out and dying of alcohol poisoning on the patio of your dorm, or scoring with that really hot frat babe and simultaneously contracting scabies...maybe it's just me...