I had the same exact problem with my 10 year old daughter and 12 year old son. I tried helping each of them, going through their respective rooms, showing them places to put things. Bottom line is that they never stayed clean and when they were it was because I did most of the work. I do not expect their rooms to be spotless always but I do expect them to be decent. Firstly, there is no eating or drinking in the bedrooms, period. This isn't only to minimize trash, it's a sanitary issue as well. Secondly, I bought each child a trash can. If I come accross trash in their room in any place other than the can, I take something away for 24 hours. I put their clean clothes neatly on their beds and they are expected to put them away the next time they enter the room. After homework, they are to put their books and shoes away in the correct place. Their dirty clothes must be kept in the basket. Out side of this, their are no other guidelines for everyday cleaning. They are to do these things before any video games, tv or computer can be used. If they break this rule, they are punished from those things for 24 hours. Now on to how I got them to keep their rooms clean all on their own. I created "weekly chores". They get paid a certain amount for each chore. Deep cleaning and vacuuming their bedrooms were included in this, every other Saturday, but with no monitary value. The catch is that they can only get paid on that Saturday and after their rooms are cleaned. No clean room, no allowance. I also do not buy my kids everything they want, just their needs a few wants outside of birthday and holidays. They are expected to save up and purchase many of the things they want. This motivates them to earn the allowance and in effect clean their rooms to do so. After the first few Saturdays, where they spent 5 hours cleaning, I explained to them that they could have their Saturdays back by picking up a few things a day. It took a few months but now their rooms are decent most of the time and they spend an hour tops deep cleaning and vacuuming. The best part is I don't have to nag them. They do it without even being told (and them remind me it's payday!) Hope this helps.