You must shelter yourself, too.
The main thing is to use brains. It depends on what the kid is up to. There is no reason that a person should feel deprived, if he is brought up normal. Your child can know that there is a world out there that people do as they wish, and we despise it. On the other hand we show them Varemkeit and Ta’am in Yiddishkeit. They aren’t supposed to be feeling sheltered. I didn’t grow up with access to movies or stadiums, but I did hear about their existence, and never thought that it pertained to me.
I’m aware of the sort of child rearing that gives way for feeling locked in and eventually breaking loose. That is when the children only hear that they aren’t allowed to do this or that.
On Shabbos in order to stop my child from doing a Melacha, I don’t shower them with notta-lattas; I remind/tell them “Shabbos!” emphatically. This is so that they know that they are refraining out of awe of “Shabbos.” When you listen to OTD Yidden rant about how they weren’t allowed to do anything, you can tell that the wrong message was imparted.
The point is that everything is supposed to be in a natural manner. When somebody’s child is r”l already not a typical Yeshiva boy, the parents must not ignore that, and act accordingly. Often times, it is at this stage where they mess up.