We know of a sixth grade teacher who announced to a group of aghast parents on Open House Night, “This is a good year for your child to fail.” You could hear the jaws drop. Most of the parents didn’t think that any year was a particularly good year for their child to fail. Now, I think I know what this excellent teacher meant. His point was that most kids who are left to sink or swim will sink once and vow that it will never happen again, and that middle school was a good time for that to happen—before it shows up on their college record. Indeed, most kids do learn by sink or swim when it comes to organization—except for those whose brain can’t help but sink when left without a life jacket.
My suggestion is to be the child’s safety net. Monitor the child’s progress while standing by closely in the background. If the child does the needed task (e.g., puts her homework in the homework folder), there is no harm to the child’s learning curve that you double-checked. On the occasional time that the child forgets to do the needed task, then fortunately, you are there to be their safety net and provide a softer landing for the child’s poor executive skills. It’s not fair that the child fail math simply because he is disorganized.
Safety nets are how they do it in the Olympics. The spotter steps in to monitor the athlete’s dangerous maneuvers, and no one accuses the spotter of interfering with the athlete’s need to take her own skills seriously. Most of the time, the spotter is not needed; but when they are needed, thankfully they are there. Be your child’s safety net. Allowing severe failure does not teach skills.