I'll counter; this sounds like me too, and I wish my parents had been more proactive. Being unchallenged but happy at the time is possibly better than being unchallenged but unhappy at the time, but the two are equivalent in the deleterious long term problems they cause. [ETA: I probably would have been good at self-advocating, too, if there had been anything to self-advocate for; there wasn't. I was often bored, but I didn't complain because, well, because that wouldn't have been well-behaved, I suppose. Besides, there were interesting things from time to time - interesting facts for example - there just weren't any hard things, and I didn't know that was a problem until much later. I think it's OK to assume that if the child isn't complaining there isn't a problem while they're very young and playing is what they should be doing, but later than that I think that's a huge mistake.]
ITA with the above.
I just read the book The Curse of the Good Girl. I think applicable here. Girls (esp. polite, teacher pleaser, perfectionist girls) are at great risk of being oversocialized to their detriment, IMO. I don't really know the answer. My dd11 is starting to have some strong opinions (usually politely expresses, but passionate and loud!) that my dh (I think it is a family of origin and cultural thing with him-German) doesn't think are appropriate in a child. I disagree and want her to be comfortable speaking up respectfully and having her voice heard. I don't know what the answer is for the OP, but I think it is a good question to consider.
