One of my first assignments at Exemplars inc. was to to replace all the clip art used in their professional development courses. As a joke, I replaced one of the images with a cartoon of my boss. After word got out of the image, consultants were asking me for their own cartoon portrait. Now our various products feature cartoons of my coworkers and our consultants.
I also had the fun experience of designing my own emojis for an Exemplars publication. I based them off the Apple set but added my own style.