I want to back up a little bit...mainly because I believe transitioning was really easy due to how we got him to sleep in his crib when he was a baby. Zane started sleeping in his crib between 2 and 3 months old. We started by rocking him to sleep and then slipping him into his crib to finish his nap. He got more comfortable being in his crib that way. As time went on, we would just put him in his crib awake and turn on his lullaby music. If you have read my page about "mommy must haves" you will remember this little device.. It is one of my all time favorite things we have for Zane. 
It plays several different lullabys and also shines a light with pictures on his ceiling. It has a timer as well.
We are "those" parents that let him "cry it out" is his crib when he was younger. And we are not ashamed of that... This is NOT easy... But for the sake of him transitioning well and our own sleep as parents, this was the best way for us. It didn't last long... He leanered quickly how to self soothe. He has always used a pacifier and I think that helped a lot and also his music helped.
If you are in the middle of this transition and you find yourself having to go into their room, DO NOT pick them up. Instead, rub their back/head/tummy, (whatever you like) and try to soothe them by not taking them out of their crib. We never started bringing him into our bed so fortunately enough, we won't have to "break" that habit. Of course he has ended up in our bed here and there throughout the past 20 months.. But by no means is it an every night thing. However, I will say that when you start it, it's easy to continue it and harder to break the habit. Zane had a few "bad" nights one week where we would bring him in our bed and it was starting a habit. We quickly noticed it and stopped it immediately. Zach and I need our bed for us. This is just our personal opinion obviously and it is what has worked best for us.
When it came to transitioning him into his "big boy bed" we did a lot of the same techniques. We started by buying him a new bed (his crib will be going to the new baby). We made it a BIG deal with him. He helped assemble it with dad and I made it seem like the best thing ever. I would say things like "oh, you get to go night night in your comfy bed!" "You're such a big boy!". I also made it as comfy as I could. I bought him a comfy pillow and comforter.
We started by taking nap in it. To make sure he would stay in bed, I would turn on his music and pat his back to make him fall asleep. It went well. If he would wake up too early, I would walk him back to his bed and do it again. It took patience some times.. He didn't always fall asleep right away.. But I was consistent and that's what matters. We did this for a couple months. We weren't in a huge rush. Again.. Consistency is key!
When we decided to transition him completely, we put up a baby gate outside his door to make sure he couldn't get up in the middle of the night and walk around the house without us knowing. We again started with laying him in bed, putting his music on, and patting his back. I didn't want to just place him in his bed after he was asleep because he wouldn't know where he was. The first night he woke up at 5 but went back to bed. Every other night, he slept until his regular wake up time.. Around 7 or so. It has been a week now and for the last couple nights we were able to just tuck him in, give him kisses, turn on his music, close his gate and he would fall asleep on his own.
Zach and I are so proud of him. He has acted like such a big boy and made the transition incredibly easy on us. The best advice I can give is to stay strong, determine the "rules" between you and your significant other so your on the same page, and follow through. If you teach them that if they cry or do "this" or "that" to get their way, that is what they'll do. Kiddos are smart and they know how to manipulate us parents. Also, start early. I knew that he was fully capable of sleeping in his own bed, so I went with it and he did great. Not every child is ready at the same time though. You know your little one and what is best for them.
I guess there really wasn't much to it for us.. Probably because it was something we started months ago and just now decided to complete the process. If you have any tips/tricks, please share!!
Oh, and we are still waiting on Nash to arrive. Currently at 39 weeks.. Today (may 17th) is the second due date they gave me... The 21st is the original. Come on, little guy!!
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