8 year old

If you limit the amount of 'stuff' he has to deal with, maybe it won't be so overwhelming. For clothing, have a shirt drawer, a sock/underwear drawer, a jeans/pants drawer. If something needs to be hung on a hanger, can he reach the rod to hang it up? If not, it will be harder for him to help keep his room clean. For toys, shelves keep things more organized than toy boxes...whatever toy they want is always on the bottom, so they end up getting everything out! But if you have shelves, with little bins for the small stuff (clear plastic shoe boxes with lids work great for this) then he can see what is there, get only what he wants to play with. A routine is important too - if he gets in the habit of making his bed first thing when he gets up, then he doesn't have to think about it any more the rest of the day. You can make that easy by just giving him a comforter instead of sheets, blankets, bedspread....then he will be able to just put the comforter on straight, add the pillow, and be done. You can make some guidelines for him, like 'All toys have to be put away before you leave for school. If there are toys on the floor, they will not be there when you get home, and mom is keeping them for a week!' You can have that same rule for bedtime too - that all toys have to be put away. If he has things he wants to do, like play on the computer, you can tell him "After your room is picked up, you can play for ____ (the amount of time that's appropriate)". If you say 'You can't play until you pick up your toys." it is more negative, and may make him think of it as more of a chore. It's also important to be really specific about what you mean by 'clean room'. He may think he can just stuff everything under the bed, and be ready to go...you may have to give him a checklist, and then use the checklist to approve his room. You could have things like: all clothing put away properly all laundry in the hamper toys put on shelves neatly small toys put together (all the army men in one bin, all the hotwheels in another bin) bed made neatly etc. Hope this is helpful - good luck!!

What I've done recently with my 7 year old is take everything out of her room that she won't keep picked up. For a bit that included her dresser, we brought it out into the living area and she had to get her clothes from there and be watched with it. She still doesn't have a lot of her toys back, as I'm trying to figure out what she'll actually keep up with and what needs to stay packed for now.

My 11 yo can't keep anything picked up either - lol. How about using a reward schedule. you get 1/2 hour (or whatever) on the computer AFTER your room is clean... I've also labeled the drawers with pictures of what goes inside. That didn't work so I took out the dresser and just have a set of shelves in the closet. This works better because he can see where things go (and it then only takes me one minute to go and straighten once in a while) He is very visual and also has poor motor function, so I give him some help with that. But I still do try and put some of the responsibility on him.