I agree, crying it out is really hard. I tried, and couldn't do it - and besides, my son would start crying so hard, he'd go hysterical and wouldn't be ABLE to calm himself down. What I ended up doing was a 5-10-15 minute thing. Put your son in his crib. Set the timer. DO NOT go back to him before 5 minutes. Go back, spend about a minute calming him down, whatever works. Put him back in the crib. Set the timer for ten minutes. If he's crying at 10, go back, settle him down, leave the room. Set the timer for 15 minutes. Lather, rinse, repeat, adding five minutes every time. (I never had to get past 20 minutes.) I also agree that having a rock-solid bedtime routine helps. It might take a few days to discover that one book works better at bedtime than another, or that one lullaby soothes while another agitates, but once you've got it set, don't deviate from the routine for the first few weeks. I swear, I've put my otherwise non-sleepy toddler to bed successfully just by starting the bedtime routine. Good luck!