I used to sit on the floor and hold my daughter's hand until she fell asleep. This worked much better than the "let them cry it out" way...i did that once and it broke my heart, and i ended up going in her room anyway after 2 hours of her screaming! Anyway, i started out holding her hand while i was sitting up so she could see me, then i moved to laying down as she could not see me but i was still holding her hand. After a few nights of that, i then would sit in her room across from the crib. Eventually i got to the point of when i was sitting across from the crib, that was when we would do nighttime songs, and when the songs were over i would leave. It took a couple of weeks for each transition, but the assurance that i was there for her made it easy. I never refused her hand if she held it out, but i didnt have to crawl in bed with her or pick her up. If she called for me at night, i would go and assume my nighttime position until she fell asleep again. Have patience. Dont let him cry it out, that will only upset you and him. Remember this is a huge change for him. Let him know it is happy and safe in his own crib. Good luck!