This seems to reiterate some of the other postings. We have a 19 month old who does excellent both going to sleep and when waking up in the morning. He sometimes talks and plays by himself for up to an hour before falling asleep or before expressing an interest to get out of his crib in the morning. Our nanny says it is the easiest sleep process she has seen and we do fear it won't be like this for any second kid. Maybe some of what we did can be helpful or maybe it is more about the personality of our son than our parenting ideas. Take it for what it is worth.
Here are some things we did or do:
1. When he was an infant, we always put him to bed BEFORE he fell asleep. I don't advocate the book due to other serious issues but On Becoming Baby Wise did give us one excellent gem - the cycle of feed/wake/sleep cycle. To not feed/bottle your child to sleep and not waiting until they were asleep to lay them down. Putting them down when they are tired but in their awake/drowsy stage which helps them learn to sleep on their own. This may be a little off schedule for you now but it may be helpful for your next one.
2. Routine is very important as well, even more so as a toddler. Evening baths and books are great. Our son understands change and we help him with transition by saying we have two books left to read, now one book. We don't pretend bed time is not coming, we embrace it. We always touch the wind chime before we put him in the crib. He has a night light, a CD playing softly in the background, and now at his age, a few items/toys he can play with until he falls asleep or when he wakes up. We say good night, sleep tight. He says it back. We blow kisses as we leave the room and he watches us. We keep it light and positive because he will read our faces and emotions. It was hard for us to know he was about to cry but we did not want him to see that in our faces or sense it in our actions.
3. We never put him in the crib if we are not ending on a good note (book, sippy cup, playing cars, cuddle, etc.). I may be tired but I don't want him to associate the crib or bed time with a negative feeling. Sometimes when he is tired and we are reading, he even gets his blanket and tries to put it in the crib and asks us to lift him up and put him in. Quite amazing to us really.
4. We did not like or want to have him "cry it out" (thought I did before becoming a mommy but promptly changed my position once I could feel the crying in my soul) but also know that sometimes the crying is just their only language. It is my responsibility to love him but also teach him and guide him. To help us learn a little, we used a kitchen timer set to one minute or two minutes or 5 minutes to know how long it really was (i.e. two minutes) instead of how long it felt (i.e. eternity) that he cried. If we first set it for two minutes, the next time it was three, and then four. This took several days to get going and may have taken longer than a full "cry it out" session but easier on us, and likely on our son.
5. As a toddler today, most nights, about 10 seconds after we close the door, he does start to cry a little but it only last 30 seconds to maybe 2 minutes. It is not a full wail but if we listen and think, it is a soft routine type cry and is his way of saying to us he is not excited about this recent development. But then he amazingly starts to talk to himself, play, or goes to sleep. But that is his routine and he does it every night. We asked ourselves how would we feel if he did not cry each night when we put him to bed and closed the door. If he did not cry, would that mean he did not miss us, did not care that we left, was fine with being alone? That made us think about what his little bit of crying meant to us and it was ok. It made sense.
6. Most importantly, we listened and used our natural parental instincts (even my husband developed them). In the beginning as an infant (6-9 months), he might cry a few minutes. We did go in and console but did not usually take him out of the crib to do it. e did take him out if he was extremely upset, distraught, etc but that was less than 10 times in his little life. Then and now, if the crying is different than normal, (louder, deeper, longer, etc.) we do go in and console him. If he cries for more than about 4 minutes, it is not normal for him. Sometimes this cycle is 3, 4 or 5 times. But eventually he does settle into sleep. Most nights he sleeps through the night, in bed around 8:30 pm and out of bed at 8:00 am.
7. We got a used video monitor because it made it easier for US to be able to see him while he was crying because we could see he was OK and not hurt or something. Sometimes you can even see it is a test and now you know not to play into it. This was one of our best purchases. Find one on ebay used.
8. Ask your pediatrician and check out the American Academy of Pediatrics website at www.aap.org as well. If your pediatrican is not helpful, consider switching to one who is.
Sorry this ended up long...hope any of it is helpful. Good luck.