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I haven't had to push him with regards to academics and I haven't had to "craft" his extracurricular path since elementary school in large part because of him internalizing the values of his peer group.
I still feel guilty that when my kids were in elementary school that I didn't advocate for them more. It all worked out in the end but only because they "lucked" into alternative programming, though it had quite a detrimental affect on my younger son's self-esteem that he has only recently in high school begun to overcome
I told D18, when she was home for college break a few weeks ago, how fortunate we were to have her as our kid. I guess we were "permissive" parents (I didn't read the article but that's what she told us compared to her friends) because she never gave us a reason to be otherwise.