This dream was about teenage Kirk. His mother was nuts. She kept calling him William Shatner. He had lots of brothers and sisters. In the dream, he had broken his leg playing some sport. It wouldn't heal properly so he was laid up for a long time. Having nothing else to do, he got way ahead on schoolwork. When he was finally able to go back to school, he was so far ahead of the other kids that he only had to take one class to graduate and that's how he got into Starfleet Academy so young.
On the day he went back to school, it was Dress Weird Day. His dad yelled at him for dressing normally and made him tie his sweater around his waist upside down and inside out. His mother was still calling him William Shatner.
I bet he was really really glad to go to Starfleet Academy even if he did have to put up with Finnegan.