Suffer with a Case of "The Almosts"

Here we are again. Maddie is putting books under her backpack instead of inside it. Then I get sweet emails giving me a "gentle reminder" to please return the daily reader and homework pages. Her teacher reports the "almosts" are a big issue with her.
Ben is doing the same thing at the house. His clothes almost made it in the laundry basket last night. Just two inches short. Why? Why not just put it in? And hanging his nice church shirts. He knows that isn't gonna cut it. It's that last step he just can't get done. He hates to make them straight so then they fall on the floor, which isn't an issue in his head but he knows it is for mom. His new solution is to thread them all wadded up through the hanger.

How do we medicate this situation? On the up side he's made a mental breakthrough that makes me happy. His teacher said Ben is struggling in math and to complicate things he's not getting enough practice time during class because he's too chatty and won't focus during partner time. He just can't ever finish the lessons. Yesterday he said, unprompted, that he can't get things done in math so he decided to just work independently from now on.