So, Wren... if I read this correctly, you were bold ("off the charts as a risk taker"). And your child was bold. So maybe you guys have the "bold gene", more than it is a nuture thing.

I often think that people who are not shy really don't "get it". It is like telling someone with dyslexia to 'just read' to tell someone who is really shy to just go and perform/talk in public/etc. I was a pretty shy kid, so I know how hard it is.

OP, we have taken small steps over the years. One of them was making a rule a few years ago that D has to order for herself in a restaurant. If she can't talk to the waitress, she can't eat. I am happy to talk over the menu with her and help her decide what to ask for, but she has to make the actual request. This was sooo hard for her. But now she does it. Babysteps...