To Enable or Not to Enable...That is the Question

One of the questions that has dogged me throughout my son's 15 years--even before we knew he had ADHD--is whether I am helping or enabling him. He has a very difficult time keeping track of ANYTHING. So does his dad. So do I. So I feel bad for the poor guy. After all, most of his friends have those hyper-organized mom's that keep track of everything and the boys either got their genes or are benefitting from them. The odds were against my kid from the beginning.

In middle school it was books. It didn't matter what we tried--rewards, punishments, organizational "tricks," this kid could not keep track of his school books. Eventually, in 8th grade, we just bought him a second set. My feeling is that it's a big enough struggle just trying to get the work done and missing books does not help! The question is, is that enabling his behavior? Perhaps if I just let him flunk all of his classes, he might remember the books? Even though past experiences tell me that, no, he'd probably just flunk and still lose books, I wonder. I know I am guilty of not letting him fail.

This year, in 9th grade, it is clothing. He is going to a very challenging college prep school and we are doing all we can to keep his head above water. We are still trying to get meds right; we've had some success but the side effects have outweighed the benefits. Here it is the last two weeks of school with football practice starting, finals coming up, and his grades are dropping again. So, for football they were given (we bought) 1 grey shirt, 1 white shirt, 1 black short, 1 red short. First week--lost the grey shirt. Creatively, he started borrowing them from other guys...however, now he's lost another guy's grey shirt. If they show up in the wrong shirt--the whole team pays for it with up-downs. Who wants to be "that guy?"

I inquired about getting more shirts, but the response was "no, because the coach wants them to learn to be responsible for their things." I'm thinking, yeah, that would be nice, but if that's the case, ain't gonna happen for my kid, right now. Maybe down the road. Maybe with practice and maturity, but not right now. So, here's the deal--I scanned in the graphics, got iron on paper, and am working on making two shirts (the other kid needs one too--he shouldn't have to pay for Brad's mistake). So is that helping? or is that enabling? I can't decide, because I feel like, despite humiliation from his teammates, it's unlikely to help him keep track of a shirt.

On the other hand, he has a $2500 laptop that he's kept track of all year...