Title: Throw Your Hat Over the Wall

Description: One version of the origin of this proverb traces back to an event regarding JFK's grandfather when he was a child in Ireland. One day while walking home from school his friends dared him to climb over the imposing wall of an estate. He threw his hat over the wall as a committment to the challenge. Since his hat was a necessary part of his school uniform, coming home without it would have had severe consequences.
The manically determined older gentleman in my illustration has a humorously low wall to scale yet he is ridiculously over prepared with hardware and skills exhibiting outdated technology.