CCN...

I see a lot of kids in my practice with this very "cautious" disposition...and it does usually get better with age. But parents are usually beyond frustrated by the time they come see me (eg: a child begs and begs to take a karate class - parent finally caves and signs child up - child refuses to get out of the car on the first day of class). Mental rehearsal can be invaluable (I had to do a lot of that when I first learned to drive) .

The advantage a parent has with school vs. an activity is that the environment becomes much more well-known to a child (daily attendance vs once a week for an hour) . The other benefit is that a child can form a bond with their
teacher(s). Then the teachers can help the child work through any remaining anxiety as the day unfolds...

IF a child is lucky enough to have an invested teacher.