Simon has a detached way of thinking, which is centered, much like Whit’s, on the bottom line, but also falls into inferior Fe thinking in how he’s lying to his family about his failing health to “protect their feelings,” which shows his desire to be compassionate and his deep love for them, but also a lack of emotional awareness (it’s the rational choice, but not the right emotional one). Howard’s emotional meltdown makes no sense to him, and the idea of abstracts literalizing themselves in the universe doesn’t fit into his established worldview, so he agrees to take a rational action generated at establishing security for his family after he’s gone. Here is all there is, but there’s also tomorrow. Simon wants to take direct, common sense actions to bring about a long-term visionary goal; the financial security of the company he helped build. He’s so focused on the here and now that Death must convince him to think about the deeper, intuitive conclusions of his actions and their potential aftermath. His vision is so narrow (when I’m gone) that sometimes, he forgets to let his family live with him “in the now.” Simon rather scorns abstracts (the idea of communicating with something unseen) but softens to them, when Death argues with him on a level he can understand.

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Simon is so secretive, his family and friends aren’t aware of his resurgence of cancer. Instead, he’s quietly working behind the scenes to reduce their pain and ensure they have enough money to live on in his absence. He’s somewhat detached from his emotions and does not want to deal with Death right away. He thinks with his head, but also his heart. His 6 wing wants to connect to others, and feels a strong bond toward his friends. He’s very logical. As a self pres 5, he’s withdrawn, likes to have his own space, and retreats to it (his home) when he feels threatened. He tries to arrange everything his family will need in advance, without drawing too much attention to it, and is unable to realize they need to know about this, so they can grieve with him.