For some children, time out's just do not work. If you feel that this is the case then I would try implementing a different consequence for his behaviour. I have a 3.5 yr old dcg who was like this. She didn't care if she was in time out or if she was in time out for a long time. She would take her time out and within minutes be back in one. I have pink and green chairs and the pink is her favourite so now her consequence is if she doesn't behave all day she doesn't get to sit on the pink chair at afternoon snack. This has worked MUCH better and she is now in timeout 1-2x a week instead of 4-5x a day!! I will also not allow her to play with her favourite toy if it is really bad behaviour. Some children need a more visual and concrete consequence than just being on time out.
She is also very spoiled at home and I would tell her parents every day about her behaviour and why I needed it to stop especially after the younger ones were copying it. Dad was on board but it took mom awhile and they now give her more consequences at home as well. Her parents are very intelligent and know what to do but they aren't the greatest at following through. Mom admitted she spoils her children and finds it hard not to do. I think by me telling her over and over every day about the negative behaviour she finally realized that she wasn't helping her daughter by not giving consequences. She is still a handful and mom still has a long way to go IMO but it is much, much better!!

































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