elh,
I was your son and I have your son. And you mentioned as well that your teachers would be surprised to find you in such a detail oriented/organizing type of position.
I have had many jobs requiring organization and attention to detail (think bookkeeper) while at the same time I NEVER remember to pick up milk on the way home and had to get checkbooks with duplicates since I often forgot to enter checks written.
I think you are right to back off on him. I know my son (5th grade) began to get more on top of making sure homework assignments came home and went back on time when they were told that a missed assignment was 50% one day late and no credit for day two. He understood that it would impact his grades and that mattered to him. I also set a restriction that all chores/homework had to be completed before anything electronic was turned on. Just these two very basic things have helped immensely and the best part is that he is self-motivated now.
Of course we still have the homework folder with papers spilling out and the organizational binder with the springing part halfway pulled out, cover ripped off and pages stepped on and missing but apparently nobody is grading on that! :-)
My son has ADHD and I felt how you felt when hearing about your son's disorganization. I had to hear about how he taps his pencil and sings and blurts out answers. During his parent teacher conference this year however one teacher told me that they were not terribly concerned or upset about this behavior. His science teacher said that DS replied "I am just being me." and that is how they see him and I have decided that from now on that is how I see it also.
We each have wonderful sons who are who they are and we love them. That is better than good enough. :-) When they find the thing that they really want to do in life they will make sure they have the skills to do it.
