Can I raise a rebel?

My son recently started going to a Montessori pre-school. It's a great school and I have nothing but great things to say about the teachers and the administrator. 

They perform various activities in class which starts with simple things such as cleaning a set of wooden blocks, then building shapes from it etc. The idea is to learn from the larger community of fellow students and learn how to behave in his community (his classroom). He is taught good manners such as covering his mouth when he coughs, conflict resolution and sharing. It is working remarkably well. I've noticed that he now waits his turn to play with a toy instead of grabbing it from the other kid or asks the other kid if he could play with it when they're done. I beam with pride when he does that. 

But I've often wondered if it is the right education style for him. The Montessori principle as I understand is that the kids learn through work. It is a very disciplined system and I've often heard guides (teachers) say phrases such as "No, that is not an option" when the student tries to test the boundaries.

I am of the opinion that "Well-behaved kids rarely make history". I love the fact that when I ask him "Would you like one pancake or two?" he answers "Three". He reminds me of Calvin and Hobbes. 

I wonder if the classroom is training him to fit well in his community thus training him to be a sheep.

I definitely don't want my son to grow up to be a felon, but at the same time I don't want him totally domesticated either.

I trust the teachers in his class to balance the discipline with creativity thus helping him grow as a well-adjusted individual whose creativity isn't extinguished. 

As a parent how can I do to help them achieve this goal? Are there measures that I should follow to check his progress in both lanes?

How can I encourage him to push the boundaries without burning himself severely? Can I test his boundaries by suggesting rule breaking? 

I would love to hear the thoughts of fellow parents or teachers. 

If you have suggestions please get in touch amjith.r@gmail.com or twitter: @amjithr

ps: I should point out that this is my own opinion and Yoshi (my wife) doesn't quite agree.

1 response
Random thoughts: We've often joked that we named our son C because when given options A or B, he'll inevitably choose option C. (And he started Montessori school at the age of 3 months.) My impression of Montessori is more along the lines of "follow the child". It encourages a child to be self-driven, independent, and trusting oneself. Children don't need to be told to test boundaries, because that is simply the nature of children. Montessori is very much about "freedom and limits", and balancing those. Because you really *don't* want a felon, LOL.