I used to ridicule J.J. as much as anybody here but as I look back on her storyline decades later I see how the deck was stacked in comparing the lives of the two exes. J.J.’s story was a partial parody of the Bridges of Madison County if Francesca had really run off with the Clint Eastwood character (and if that character were more of an idiot). Trudeau likes to ridicule her artwork but she did get commissions and also drove a cab to help make ends meet. Before she left Mike he was wallowing in a depression and not doing anything to try make changes.
In the flip side of the story, Mike, a conflicted, very depressed ad man selling his soul to flog the Mr. Butts campaign among other things, has a series of summer fantasy dreams magically come to life to change his circumstances. With no effort on his part he is whisked to a great home in Seattle with a great paying job provided by an old college friend, and has a very young trophy girlfriend (her joking words later) dropped in his lap. As J.J.‘s art is parodied (I think just by being art – for some reasons cartoonists love to ridicule art), Mike and Kim’s startup will be very successful but essentially providing a product that does nothing (which was part of the parody).