Work that pole... was a creative fluke produced by someone who could not/cannot/will never be able to draw, Katie Mercer.

One night while doodling, she found herself laughing at her "drawings." This laughter was a product of disbelief that she could make out what it was that she was drawing and the realization that the drawings were actually a bit humorous.

Work that pole... is her attempt at spreading the humor.

All of the drawings in this series [including the logo] were hand-drawn without the use of a ruler, obviously.