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You need to read "Summerhill" by A.S. Neill as soon as possible.
Summerhill is/was a "free school" in England for children. The basic idea is that you should not be punishing, nor rewarding, nor forcing your children to share, nor forcing them to do pretty much anything assuming they will not be in danger. This includes going to school and drinking milk.
Obviously the anti-traditional school part will be a big problem for most of us since most of us are not able to homeschool, and even if we could, children need (?) to socialize. But just employing these parenting principles in your home should be enough to lessen the harm that regular school does.
Note that this has nothing to do with letting your children walk over you. You can tell them not to track mud on the kitchen floor, but they can tell you to stop playing with their toys or to get out of their room, and you have to listen. Equal rights.
Your description of your current social skills makes me think of "children should be seen and not heard". If as a child you were brought up to only speak when spoken to and to keep it short, it should be obvious what effect that would have on you as an adult.
The biggest positive thing about children raised as "Summerhill" kids is that they are supremely confident. They have no insecurities about authority figures and no social awkwardness. Supposedly when they go on job interviews as adults, the interviewers remark that they have never seen such a confident interviewee.
This is an updated version of the book, not the one I read, but I'd imagine it's as good or better:
http://www.amazon.com/Summerhill-School-...6542&sr=8-1
It's possibly the most important book I've read, whether I ever have kids or not.
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I remember a psychologist saying her 8 year old son still wore diapers day and night and regularly pooped them. She said he would decide himself whether that would ever stop being a good idea, and she didn't want to hurt his self esteem by being judgmental about it or applying any kind of pressure. She was very sure that he was much happier and better adapted to his social environment this way, without any "unfair" pressure from her.
I think these things can go too far, and very easily.
I also think they are often a cop-out on the part of parents who don't want to do the sometimes emotionally trying, harder work of being parents, and cover it up with blather about love and freedom and encouraging self-confidence and refusing to terrorize their children with unfair demands.
It's a hell of a lot easier to be the "nice guy" parent and pass it off as enlightenment than to take responsibility for your kids and risk them giving you a sad face or having a cry.
Some of the long-term effects of this sort of thinking and this way of raising kids seem quite a bit less than rosy to me.