Sleep Baby Sleep

When did you start letting your baby cry themselves to sleep? My baby will be a year in a few weeks, and he is a terrible sleeper. It is hard, cause it seems like he was waking up so much because of his ears. Now he is so used to it that he doesn't know how to sleep through the night. I know I need to let him cry, but the problem is that he is in our room. We only have a three bedroom house, so he's with us. This week, I want to put him in with Ellie, then I'll let the crying begin. I am so ready for a full night sleep.