I mean this in the kindest way possible, but I am honestly exhausted by your expectations just reading this post.
You have a clear and fully-defined view of the pathway forward, but your DS does not seem to be complying. You're trying to think up Plan B and C and D, but they are still deeply embedded in the Plan A vision. I get this, I really do. These kids are so challenging and confusing, when you think you’ve finally figured out what you are doing, it’s hard to let it go. But I think you really need to let this go.
I came into parenting with a ton of plans about how to make sure that my kids did not have to live through all the things I hated about school. But my kids are so completely unlike me that those plans ended up being pretty meaningless. I learned the hard way that sometimes as a parent I really need to just stop, step back, take a deep breath, and try to take a new look at my kids and their environment, one unclouded by prior assumptions and what worked for me, or worked for my other kid.
What might you see with a fresh set of eyes? As a complete stranger who knows nothing more than what you've written, here's what I see:
* An extraordinary young man, successful and high-achieving in life. He's happy, has great friends, and is himself a great friend to others. He’s kind, helpful, loving and lovely.
* He's a hard-working and ambitious entrepreneur, creating businesses that involve making plans, putting in the big effort and carrying through. He gets a lot done.
* He’s creative and innovative, and marches to his own beat. He finds opportunities and comes up with good solutions, and they aren’t the way other people would do things.
* His school environment is a bad academic match, and doesn't come near to meeting his needs.
* He has (remarkably) tolerated that lack of learning and make-work well, and still got high marks every year up to now. Currently, however, he is giving school the level of effort it calls for.
* He is what, about 11, 12? This is an impressive young man!
* He is not his siblings.
The best advice I can give you is, if you want him to work hard, give him hard work.
If you haven’t read “Is it a cheetah?” lately, the words “zoo chow” are echoing loudly in my mind. Your son sounds like a kid who desperately needs some antelopes and a wide-open plain.
http://www.stephanietolan.com/is_it_a_cheetah.htm Some kids can brush off the make-work, just jump through it and quickly move on. Others find it soul crushing, and just. can't. do. it. (And some kids with ADHD are genuinely incapable of keeping their attention on meaningless work, no matter how hard they try.) Note I said *can't* do it, not *won't*. This doesn't sound like a discipline problem, it sounds like a bad school-fit problem.
His siblings thrived despite a poor-fitting academic environment. They were able to comply while finding their learning and challenge elsewhere, outside of school. Some kids can do that. Others just can't. It's not a matter of trying harder, it's about not being able to function well when your basic needs are not being met. So what kind of environment could better meet your son's needs? Is there a schooling option where he could get much more complex, engaging, challenging, motivating, harder work, sooner? What school and/ or activities would value and feed his entrepreneurialism and creativity, and love the energy and passion he brings to them? (I am guessing from the way you describe his school that these strengths likely get seriously in the way of his current school work).
I would be cautious about approaches that will almost certainly, as aeh wisely notes, exacerbate the problem by increasing the bad fit of his academics. Running his zoo chow through the blender to make pablum is not going to make him run faster. Easier work and grade repeats aren't going to provide challenge and engagement, and may just feel punitive, too.
Instead of thinking of ways to make this child look like he is on the same pathway as his siblings, what are the different kinds of pathways that could work for him?
