DS (currently a freshman at an SMC) was homework-challenged starting in 3rd grade. By the time he was in 7th grade, I decided the best course of action was to let him learn from his homework mistakes and make his own decisions, hoping that he would see that not doing homework on time or not completing big projects on time would cost him on grades. It cost him big-time.
By the time he DID learn from his mistakes, it was too late -- his grades were in the tank, he had developed bad study habits and he suffered through 9th grade not really prepared for high school work. He's naturally really smart, and once he buckled down academically and started completing projects on time, his grades skyrocketed. But by the time all of that came together, it was 2nd semester sophomore year and by then it was too late and his GPA and class rank would never recover.
He is very smart, having tested 4s and 5s on every AP exam, getting college credit for 5 core college classes, so I think he probably could have been competitive for academy admission. (He had all the other stuff -- leadership, sports, physical fitness, and most importantly, the desire to be an Army officer dedicated to doing whatever it takes to serve his country.)
Now he's doing great academically, physically and mentally at his SMC, and he's on course to go AD with a high GPA, leadership positions and great PT scores, but I kick myself every day for not pushing him more when he was in middle school. He would be killing it at WP, happy to be occupying a spot Haleym says is taken by some guy who doesn't want to be there.
Some middle school kids have it all together and don't really need to be pushed -- they thrive on making all their own decisions. But some kids need more direction. I wish I had pushed my son more.
DS2, a current 7th grader who, if left on his own, would choose never to do homework, is the beneficiary of his older brother's mistakes. Not a day goes by when we don't look over his class requirements, grades and homework assignments together.
Will DS2 be prepared for high school work? Will he graduate with the highest possible GPA? Who knows. All I know is, there's no money for college, so I'm doing what I have to do to help him be competitive for scholarships or admission into an academy if that's where he wants to be.