A few ideas popped up right away. The boingboing mascot, jackhammer jill, seemed like a good jumping off point.
My first idea was to have jill repairing something, off in the distance, with sparks flying out of her welding or soldering equipment. This is a cliche of broken pages, insert mascot with toolbox and welding goggles. Also, since the site was not technically broken, just a page which did not exist, I scrapped her working on fixing something.
Another idea came from her resemblance to a lumberjack, which brought to mind john cleese's song about being a rather odd lumberjack, dressing up in womens' clothing and eating scones with tea. So I had her taking a tea break, considering the message: "ERROR 404: you have walked into a tea party, what will you drink?" with an image link back to home page, options being tea or to leave. Tea always makes me thing of the psychedelic tea party ritual of the mad hatter and the march hare, with that poor effed up little doormouse in the tea kettle, zonked out of his gourd. So, I wanted to animate a simple gif of the little guy popping out of a tea kettle occasionally. This idea was a little too much of a tangential stream of thought, so I cut back on it a bit to simplify.
I thought, Jackhammer Jill is out there, putting holes in the ground, she must be a member of a worker's union!( Especially with the left-y writings of the staff), so, keeping the break for a drink idea, I put her on some I Beams with a thermos and a mug, a classic symbol of union breaks, right after guinness. The text will read, in a digitized font in going with the style of jill's rendering: "ERROR 404: UNION BREAK: This page has not been worked on."
