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I personally don't think time outs work at this young age but I think it is good to start the process. Right now my 26 month old thinks it's funny to put others in time out. I just don't think the connection is quite there yet as to why or what time out means. I try mostly re-directing the bad behavior when possible. I also don't keep him in time out for long because again I just don't know how much of the connection to the bad behavior and the consequence there is just yet.

I think holding him in time out is working against you. I understand the dilemma, but you may have to do a couple hard days of returning him to time out (even if he immediately leaves it) over and over, with no talking to reinforce the point that time out is separation from you and the behavior (he hits you, so you need to be away from him to be safe).

I started time-outs a little past one with a quick separation. I just carried him to another room, set him down, and walked away. He immediately followed me, which was fine, and then I explained why I didn't like the behavior. When he hit two, we had a time-out spot, and it only took a day of putting him back in his spot for him to get it. He rarely visits time-out these days (and it's not my first move), but I do think it's an important tool for us.

@Jess1483: Yes! I forgot that we had to do this early on as well. He would follow us initially until we had to put him back. That did seem to do the trick!

@AggieDaze: If I catch him in the act, I will sometimes say very sternly, "Excuse me...we do not hit. Mommy and daddy do not hit you, and you should not hit other things (or us)." I will pick him up away from whatever it is that he hit, hold his hands and explain why we don't hit.

Just wanted to chime in and say that 21 months was the same age that Xander started acting out more and he started doing things just to be put into timeout. And then shortly after that, he started putting his stuffed animals into timeout for random things. But it was a short phase that he went through because even a couple months later, he wasn't acting out as much.

A lot of kids need rehearsal and repetition to process new things liked time outs, so it's possible that your LO is asking to go to time out and doing things purposefully to go to time out just because he needs the consistent practice with this new thing. I would expect that after a few days of it, he would go back to thinking time out is aversive. But I agree that you should use the crib instead of holding him because the whole point of time out is the lack of attention. You don't want it to turn into a power struggle of having to make him stay in time out.