Each child is different and I can only tell you what worked for me. Some people might not agree with my tactic for philosophical reasons but it worked for us beautifully. I started letting ds (27 months) fall asleep on his own about a month ago (because I am pregnant too). Basically, I explained to him as we went into the bedroom one night that we would read a book, say a poem, say our prayers, and sing a song, and then I was going to sleep in Daddy's bed. He understood completely. We went through our ritual. WHen I told him I was going into Daddy's bed, he begged me to stay but I bribed him with a cookie ("If you stay in bed and go to sleep by yourself, you can have a cookie tomorrow"). He brightened up and went to sleep without a peep and the next day I praised him and bragged about him to dh and gave him his cookie. I had to promise him a cookie for about a week, then stopped bribing and he has done marvelously. After we talk and sing a little, I simply tell him where I'm going and that I'll see him in the morning and we'll make oatmeal. I think the biggest thing was that he could understand what I was saying and he could comprehend the idea of tomorrow. If you are sure your child can fully understand what you are saying to him, then you shouldn't fel guilty about teaching him to sleep on his own. It might be a little frustrating to him if he's slow to embrace change, but that should be the extent of the negatives.