Pigeon from Mo Willem's Pigeon series--Bus Driver. Obviously. Okay, I had to do this one. Out of all the names on this list, Pigeon's future career is the one I'm most confident about. He WILL be a bus driver.
Dorothy from The Wizard of Oz--Disaster Relief Worker. Anyone who survives flying around in a tornado seems destined to be a great disaster relief worker.
The Boxcar Children--Own and run a bed and breakfast together. 99% of The Boxcar Children is just a love story to playing house and these kids enjoy nothing more than playing house. Hopefully they come up with some different meal ideas before they open their bed and breakfast, though--bread and milk for every meal would probably get pretty old for their guests.
Mars Bar Thompson from Maniac Magee--a crossing guard. As a former crossing guard myself, the need for people who can legit stop traffic is a skill (You wouldn't believe the number of people who drive AROUND crossing guards stopping traffic!). If Mars Bar could do it with just a glare and a mosey, imagine what he could do with a stop sign and a yellow vest.
Max from Where the Wild Things Are-- The dictator of a country. No offense to Max, but when he was the ruler of the place where the wild things are, he was a big time despot.
Female Dog wearing hats from Go, Dog, Go--A dog milliner which is just a fancy way of saying a hat maker for dogs. The party hat at the end of the book was a little crazy for my taste (who puts a mop on a hat?), but the one dog seemed into it, so what do I know?
Frances from Bread and Jam for Frances--A professional jump roper. Is professional jump roping even a thing? A quick google search tells me that yes! This CAN be a career! And not only that, but the average salary for jump rope jobs is $57, 679! I'm shook. Basically this is a real thing that will pay Frances's bills.
The Little Engine That Could--A motivational speaker. The little engine was at the forefront of understanding the psychological benefits of positive affirmations. So not only is he inspiring as all get out, he's a trend setter to boot.

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