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How do I get my baby to sleep by himself?

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I have a 2 mo old. He sleeps with me in bed and want to have him sleep in his bassinet or crib. I put him in it for his naps and he wakes up within 20 min and wants to be held until he falls back asleep. This goes on for a while. At night it's a hit and miss of him sleeping in it for up to 2 hours at a time. I put him in it "sleepy but awake" and that just makes it worse. He won't go to sleep for at least another 30 min. I don't have patience for it so I end up being lazy and let him sleep with me. When is it good to let him "cry it out" ? I find that I can't let him scream, my instinct is to tend to his needs. Help. I'm a first time mom.

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