"talked about joining the air force when he was old enough and maybe becoming a pilot"

Jimmy has a lot to achieve if he wants to become a pilot in the air force. While the necessary steps have changed over time, if Jimmy wanted to become a pilot in mor emodern times he would need to complete a bachelor's degree program. He would then need to earn commission as an officer. There are numerous tests and training programs that would follow. It's definitely not something Jimmy could decide to do on a whim.

WikiHow: How to Become an Air Force Pilot