I have a similar issue. Kaji is 3 and scared of his own shadow. However, I've only had him since he was 1. What I am trying to do is expose him to everything I can, and it all has to be a super positive experience. He's gotten better over the years, and has his favorite places, people, and play mates. This includes much larger dogs. I just keep trying. My dad gets mad at me all the time because Kaji is stressed the first 15-20 mins of any trip. To me, that is a huge improvement! He use to be afraid the entire trip, and slowly has learned to relax. Not completely, but we're still working on it.
