Drew has pinned his entire career on a single dream – a wonderful, magnificent shoe everyone was sure was going to be the next big thing… and then, flopped on a spectacular level. Even when going through the events of the aftermath of this, Drew cannot stop intuitively speculating on the meaning of things – “last looks,” etc. He’s withdrawn from reality and unable to imagine what to do with his life, unable to find purpose, and forced to cope with losing his dad, but even then he’s still fixated on his epic failure, and how in the immediate future, it’s going to look terrible. In his worst moment, Drew impulsively takes all of his stuff, the entire contents of his apartment, out to the dumpster, and rigs up a bicycle to kill himself with – in a grand effort to end it all. He lives so much in the moment, he’s self-destructive and unable to envision any future for him until Claire forces him to take a road trip, open up to new experiences, and find her again. His sister says Drew can handle the funeral, because he’s always the one who keeps it together and solves things when they go wrong. Drew does manage to remain stoic and withdrawn through most of the events in Elizabethtown – he is socially awkward, unsure of what to say (saying “Condolences” to everyone he meets, in a formal fashion, and not realizing he ought to be the one receiving condolences), and unable to connect to his family. He was often busy pursuing his career and chasing achievement, rather than staying close to his family, during the last years of his dad’s life. Drew spends half the film in a Ni/Fi loop, fixating on the future fall out of the shoe disaster and his emotions – admitting to Claire that he’s a massive failure and can’t deal with other things right now. He waits to break down over his dad until he’s on his road trip, alone.

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Drew wants to be a success. He works hard for it, he feels elated when he gets it, and sinks into utter despair when it’s all stripped away from him. He becomes more and more dejected, as his boss tells him what a catastrophe this business venture is going to be. Drew can’t stand failure, or the public humiliation, so he dramatically, in a 4 wing fashion, decides to end it all – in a very artsy way. His 4 makes him self-searching and introspective, causing him to sink into a deep cycle of depression until he meets Claire, who challenges him to get over it. Drew is lethargic and unmotivated after his failure, showing the worst of 9 disintegration passive tendencies (not wanting to disappoint anyone, trying to pacify both sides of the family, and having no desire to try  a new profession).