I met Jerry Craft last week at Avon Free Public Library's Children's Authors Night. Very soon thereafter, Publishers Weekly included him in an article on a book he illustrated that is being published this month by Scholastic.
Here's what I find interesting about this: Jerry self-published his first Mama's Boyz book in 1996. And now he's illustrating a book for Scholastic and getting written up in Publishers Weekly! But it's not 1996 anymore. It's 2014. Jerry didn't go directly from self-publishing to working with a traditional publisher. In between he's worked as a cartoonist on graphic novels for Marvel and Harvey Comics, his cartoons have have been syndicated through King Features, where he also worked in sales, and he was the Editorial Director for the Sports Illustrated for Kids web site. He's also done covers for other authors' self-published books.
My point is, he did not self-publish a book and become some kind of over-night sensation. He maintained creative day jobs while working toward success. To me, this is a great and realistic career model.