You could be describing my DDs 1 and 2, except my #2 also has an anxiety disorder, which meant that I really couldn't push her too much or else she would just have a major meltdown and we would go backwards.

DD2, 4 yrs 5 mths now, started kindy this year and I was incredibly worried about how she would cope away from me, and in an environment that I felt would be at least initially completely overwhelming for her. She did really well, although remained quiet and shy for the first term. Now her teacher and TA are telling me how incredibly well she is getting on, she's volunteering to get up in front of the class to sing a song, answer questions etc. She has a really tight little core group of friends but is generally incredibly well liked by the entire class - she was off sick for a fortnight last term and when she went back there was a chorus of "Yay, E's back" from lots of the kids.

She is still very shy in situations outside her comfort zone but I don't push her. If someone in a shop tries to talk to her and she doesn't engage, then she doesn't engage. She is pushed to say please and thank you wherever its appropriate but that's it.

Its taken me a while to get past the point of trying to "fix" her so she is more outgoing like her sister. She is the little person she is and she'll find her own way. I now have the opposite problem with her elder sister in teaching her that it actually not ok to just volunteer any and all information to complete strangers!