My son is immature for his age, but academically, age appropriate. The problem is that he doesn't seem to care about the work that he's producing...his writing is sloppy and almost unreadable, his work is rushed through and directions are not followed. He is in the third grade. This is the first year that he has received D's and F's routinely. In second grade, he ended the year in the top 5 of his class. I know that third grade is hard for some kids to get used to, and he is finally starting to show some improvement, but it has been hard fought with A LOT of support from me, reviewing his homework and having him do a lot of corrections. We are considering holding him back and having him repeat third grade. I would appreciate any insight or advice from parents in the same position and hearing what criteria you considered when you made the decision to hold your child back or what encouraged you to not hold them back (if you were at that point of having to make that decision). I would also love to hear some advice from parents that did hold back your child, what you said or did to keep encouraging them to move forward and not hold any resentment or have feelings of disappointment in themselves.
edited to add, in response to comments
I do volunteer in his class once a week and do notice that he is easily distractable and has a hard time sitting down and paying attention like the other kids in his class. I must make note of the fact that he was born at 29 weeks and my father is convinced that prematurity does extend past the age of 2 years old. His birthday is in May and he was just shy of 5.5 years old when we started him in kindergarten. I will say that his teacher has a notorious reputation for talking down to the kids and yelling in class...but he has repeatedly assured me that he likes his teacher and is not afraid of her. She does have a much different teaching style than the other teachers that he has had before....she's much less organized and does expect the kids to "get it" without much explanation (her attempt to encourage independent thinking). I am also not just focusing on his grades...he seems to be failing a lot of tests and classwork just by not paying attention to the directions or completing timed tests (which he used to ace). His teacher has mentioned to us that she thinks it would be a good idea to hold him back due to his immaturity (lack of pride in his work, failure to follow directions, unable to sit still in class, sloppy penmanship, trouble with comprehension when tested on stories that he's read, etc.). We definitely do reward his improvements...he gets to go dirt biking with Daddy for one-on-one (his most prized possession is his dirt bike) when he has good weeks at school and he just earned his first weekend out. He also gets extra x-box time, extra online computer time...both of which, he lusts after. We restrict or take-away all of his time on x-box and the computer when he has bad weeks.