How Do I Know If What I Am Doing Is The Right Thing To Do?

I am struggling with homeschooling. I don't know if what I am doing is the right thing to do.

How does one make a student CARE about his education? My son has been doing his typical mediocre work, where his studies are concerned. How do you motivate a person to do his best and take this seriously?

At this point, I am making him review his DVDs and retake quizzes UNTIL HE PASSES THEM, no matter how many times it takes. Is this the right venue? How will he ever be a self-sufficient person if I have to constantly follow behind and see that his work gets done? How will he ever feel "smart" enough, if I don't keep at him to LEARN these subjects that we have before us now, in order to lay the proper foundation for what is to come? This lack of knowledge will only exascerbate his difficulty in his future studies, if he does not master the material that is presently before him.

I don't know if I am enabling him to fail by staying on him to get this in his head or if I am dooming him by letting him fall short of what I know he needs to learn.
If I make him repeat this work, am I keeping him from maturing enough to do things on his own? Or, am I failing, as his teacher, by letting him fail and suffer the consequences?

I find myself at a loss and that is a place that is unfamiliar to me. I am so uncertain which is the proper path to take. If he doesn't clean his room, that will affect him for a time, but it will not alter his entire future, so I don't sweat that. If he fails, yet one more time on this school work, it could damage him in so many ways...both psychologically and physically, it can skew his future into something that he, nor I will be able to accept.

I am reminded of my English/Lit. teacher from high school. He would answer every question on our study sheet. He would give us the answers as he expected them to be, verbatim. There may be 100 questions on the study sheet and only 50 on the exam, itself. We HAD to learn all the answers in order to pass the exam, because we never knew which 50 we would find on that paper. If we did not make an acceptable grade, he would keep us in at P.E. or studyhall to repeat the test...until we passed with a grade, he thought appropriate. He FORCED us to learn the material or pay dearly for it in time spent taking the same test over and over. He is my inspiration for my theory of drumming this material into my son's head. But it was a different time then and I don't know if I am impeding my son's progress by holding him where he is, until the subjects are understood and remembered.

We are behind in his studies, but I am diligently working to get caught up. This has not been the school year either of us envisioned. He is even talking about the possibility of going back to school next year, so I know I am doing something right. By that, I mean this year has not been the piece of cake he thought it would be and that is encouraging.

I just wish I knew how to make him understand how this will affect his future. How it will impact his choices for further education, how it will make a difference in what career opportunities he will encounter, how it will matter to him someday, when he has a wife and children to support.

The one bright spot is this...I have learned from my shortcomings with my son and I am not repeating them with my girls. I no longer "do" projects for them, I no longer run home to get what they forgot to pack for school and drive the 13 miles, one way, to take it to them. Those days are gone and I know, they will be all the better for it. They are allowed to suffer the consequences of their actions and I am the soft place for them to fall, when things get hairy...the way it should be.

I don't think it is a parent's place to meet out punishment and discipline as much, as children grow older and become closer to plotting their own course in this big world. I think that the consequences they suffer at the hands of life (within reason) is usually all that is required. If the price life requires is painful enough to change their behaviour, then I am happy to be there to help them pick up the pieces and put it back together again. If life's consequence is too easy to overcome, discipline will be exacted by their parents.

My biggest fear is that I have coddled my son into a complacency that he will not be able to overcome. I pray that my wisdom has not come too late to be able to benefit him in the long run. That will be a difficult pill to swallow, indeed.