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Trevor,
My teacher noted that expectation is more of a result, a fruit. The problem isn’t expectation, its grasping. But even that is more like an ignorant habit than evil. For instance, in your post perhaps you have an expectation of some answer satisfying you, bringing a sense of comfort or stable ground. But it doesn’t, and not because expectations aren’t being met (ironically, your expectations are being met, your mental energy completes pictures, fills in gaps to make things fit what you believe to be true), but rather from “jumping onto” the restless grasping for some idea to bring peace.
When we can sit with our restlessness, it goes away. Then the questions you pose produce laughter, not hopelessness. A cosmic comedy, not a tragedy. Yep, a snake eating its own tale… and here we are, restlessly looking for something we inherently are. Hahahahaha.
With warmth,
Matt