Jonathan is highly emotional, very aware of how he feels about things, and tries to pour that emotion into his work by focusing on what matters to him, sometimes to the exclusion of what makes sense to his audience. Directors and participants at his first live workshop complain that his story is not linear and seems disconnected, that they can’t find or follow a main thread, because his plot is all over the place. Jonathan has a few things he is deeply passionate about, because they have touched him and the people he cares about, such as AIDs. Even though it’s been eight years of working on the same musical, Jonathan is still hammering away at it, finding it difficult to work on anything else, because this is his baby and brain-child. He keeps his mind busy by writing jingles while he considers whether he could do that for a living – instead of writing the last song for his new musical, even though his friends push him to get after it so he can be done with the process. If he can’t think of anything, he can’t write any of it. Instead, he gets caught up in his feelings about turning thirty and not yet having achieved success. He feels pressured to create something brilliant and share it with the world, but doesn’t completely know how to start doing it, how to launch into the world, or even how to keep himself out of the poorhouse, because he doesn’t look for roommates to pay half the rent. (He has gone through a dozen of them in a couple of years, and is far less practical than his actor friend who went on to work in a company and give up on his dream.) Jonathan struggles between practicality, and an all-or-none approach; he takes a job writing jingles only to throw up his hands and say he can’t do this, and make light of the entire thing, causing him to get thrown out; then turns around and says he’s tired of living hand to mouth, he wants a nice studio apartment and to make money. Though others complain that he has to do what he hates to earn money, he points out to them that it costs a lot to put on a musical.

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Jonathan can be rather self-absorbed at times; when he’s wrapped up in his creative projects, he ignores his girlfriend by not answering her phone calls, and failing to realize she can see from the street that he’s in the apartment and ignoring her calls. He doesn’t really have an answer for her about joining a ballet troupe and dancing in another state, because he doesn’t want to leave New York and his dream to help her pursue hers. He finds it hard to do things he doesn’t want to do, like the unglamorous job of working writing jingles (instead of award-winning musicals), and actively resists incorporating anyone’s ideas into his work that he doesn’t deem worthy, such as award-winning Broadway musical writers or directors. Even then, if his heart isn’t in it, he can’t write it – dragging his feet about composing a song in the second half to link the two wholes into a more cohesive piece of storytelling. Jonathan also battles an almost-constant pressing need to achieve, to show everyone his worth, to get something done, to produce a musical that people want to see, and to make a success of himself. He berates himself for being thirty and not yet having made a success of his career, comparing himself to the “giants” on Broadway and seeing himself as lacking because he can’t finish this musical. He’s devastated when people respond positively to his work, but then shrug at the idea of producing this musical and “can’t wait to hear what he does next,” because this is his whole idea, his life, his identity. It’s hard for him to walk away from it to focus on “what I know” (although, that pushes him to create Rent).