What type of temperment is he? Where does he take his naps? Are you planning to stop breastfeeding any time soon or do you plan to continue for a while longer?
With his birthday coming, you could use it as a way to make "Big Boy" changes. You can start talking about how he's growing up and how he's such a big boy now and that he's going to be getting his own big boy bed, for example. He can help you pick it out, get a blanket and sheets, a special lovey, etc. Get him really excited about the whole thing. Then if he's not taking naps in his own spot already, start there with the intention of building up into him going to sleep on his own in his own room. Pick up put down will still work with a little guy his age, but it will most definatley be a struggle. Do it on a weekend, and have HELP.