Supernatural Headcannons

What if?

Had John left the boys with Bobby instead of dragging them around with him in search of the yellow-eyed demon, they would have been raised correctly, (as seen in a flashback with Bobby teaching Dean baseball instead of shooting, like John had wanted).

This would have provided a safe and nurturing environment for the boys growing up and would have actually made both school and hunting a possibility for both Sam and Dean had Bobby even taught them how to hunt (this balance can be seen with the teenage gang of hunters who go after vampires).

Dean would thereby be going to school and pursuing a career because he wouldn't have been beaten down by his father, which would possibly be something manager-like, given how easily "Dean Smith" was able to fit perfectly into a manager's position at work, without former knowledge of how to do so (that was not placed by the angel Zachariah).