Rane didn't join the military, he flew for himself. He took jobs from various sources, although it wasn't easy due to the Empire's restrictions on travel and trade.
His younger brothers later decided to become pilots just like Rane. Unlike Rane, they thought they would be better off by joining the military to get "free" pilot training. But they didn't check with one another before joining, and soon discovered that one brother had joined the Imperial Navy and the other the Rebel Alliance Navy. It came to heated arguments as neither of them wanted to leave his organization to join the opposite faction while Rane tried to help both his brothers.