J.P.
My son will be 3 in April, and when I had problems keeping him in time outs, I would just hold him there and tell him he would have to sit until he settled down. I always explain to him that his choices cause the time outs. He does understand that. I would keep sitting him back down consistently until he just realized that it wasn't worth it to get back up. If he is crying about having a time out, I tell him he has to settle down, and I don't start his 2 minutes until he stops crying and settles down. I explain the reason for having a time out and that he needs to sit nice and not scream every time he has one, so that he understands. He seems to really understand, and it is not often that he even needs time outs anymore. If he gets a warning, usually he stops whatever he is doing (or does what I want him to do) right away. I always give him a chance to avoid the time out by listening first, so that he knows it is a consequence of his choice and not mine. The last few months counting to 3 has also started working well, if I get to 3 and he doesn't listen, he gets a time out. Now when he gets a time out, he always says he wants to listen, but I always give him the time out first and tell him it is too late, you have to listen when you are told, not when you are in a time out for ignoring me. He was doing great, but the last few weeks he has had a lot of change (started preschool, potty trained), so he is going through a phase of not listening well again, but I know that if I stay consistent he will settle down and do better when he gets adjusted. Good luck! I know how frustrating a 2 yr old can get, especially when you are the only one doing it, and working too!