Our solution has been to set specific parameters and guidelines for tough situations for him:
1-When it's OK to disobey (If someone asks or even demands that you do something unsafe, unkind or hurtful to you or anyone else, you have every right to say 'no way!'),
2- What is the appropriate way to ask mom or dad or other grownups in charge "why do I have to?" (You may ask 'why?' as you are moving in the direction of obedience OR you may ask if it's OK if we talk about it first- but you may NOT hold your obedience hostage by standing cross-armed until you get a satisfactory reason. You need to trust us.)
3-When immediate obedience, no questions asked, is required. If mom or dad say something is not up for debate right now, you must trust that we have your best interest, safety and well-being in mind and believe that we will help you understand later (the middle of the road is not the time to ask why we have to hurry across!)
These specifics have been helpful for our little analytic guy, but they don't cover every situation and they don't always take away all sting of an answer that he doesn't understand, doesn't agree with or is simply disappointed by. The grey areas, where I am tempted to simply say "because I said so" can be the toughest. He is smart, he knows what he wants and he doesn't want to be stopped. It is tedious to have conversation after conversation about what feels to me like the same issues, but I am convinced that it's essential to the type of mother I want to be and the type of son I want to raise. I want him to know that his trust is valuable and it is to be given where deserved. I want him to know that his desires matter and that in any relationship he enters into, who he is, what he thinks and feels should always be part of the equation. I want him to know that sometimes, not getting what you want doesn't mean you are unloved and that being angry at someone doesn't mean you don't love them. I want him to know that there is always a chance to turn around, say you're sorry, try again.
And so, when all of the above tools failed last week and I had to firmly say, "I'm sorry that you don't agree, but I have heard your point of view and I am still choosing to say no for reasons A,B and C" he was angry. Angry enough to say something hurtful. Angry enough to say "I wish I never had parents, just like Huck Finn! That way no one could tell me 'no' all the time!" (note the literary reference in his fit of rage). I took a deep breath, I let myself be hurt, I let him see that he had hurt me and chose to respond kindly and honestly, "That's an unkind thing to say. I think you should think about if that is really true. I love you but I am not happy with how you're responding to my decision and I don't like the way you are treating me. I'm going to go finish my work now, but when you are ready, I think you'll need to ask my forgiveness for those words." He looked sheepish and somewhat embarrassed, but he did not apologize right then. He went to his room to work on some lego project while I went to my office without another word.
I wondered if I had failed, if I should have punished him for those disrespectful words, if I should have demanded an apology right then and there. I tried to remember my hope for him. I prayed and I waited. That evening, I walked into my room, spent and empty, to find this little note on my bed and I was reminded of the grace that can enter in when we make room in the broken places.