Oddly enough, I think I'm the one who's been too accepting of my own personality traits. Both of my parents and my older brother have always been very outgoing and extroverted. I was always much quieter and have trouble in large crowds or groups. For awhile, I just sort of accepted that I wasn't going to be the outgoing one in the family. Once I moved away from home after college (and stopped feeling like I was always so-and-so's daughter/sister), I had to learn to be more extroverted and I think it sort of paid off. As it happens, my mother (one of the most extroverted people I know) always tells me how painfully shy she was as a child and young adult. And when I stare at her in disbelief, she tells me she had to make herself be more outgoing until she learned how to do it naturally. 

I think sometimes we need that (gentle) push to at least try something different b/c some of us (like me) wouldn't necessarily try to do things differently unless we had a reason to. 

(Side note: the image of you at the parent-teacher conference made me laugh. My parents always told me they would listen to my teachers praise me and then look at each other and wonder, "are they talking about the same Meredith we know?!?")