First night early bedtime and sleeping in his own bed

A big fat fail.

My son has always just gone to bed when we do, falls asleep in my arms, then sleeps next to me in our bed. Last night we tried winding down early, rocking him to sleep and putting him in his bassinet so we could, for the first time in almost 8 months, have a couple quiet hours together. Didn't work. Then I tried putting him in the bassinet multiple times throughout the night but he wakes up immediately and I have a very hard time listening to him cry.

Any other moms just starting this bedtime adventure? What routine works for you?