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"'something just refuses to click when I try to plan it out at the chapter by chapter level." The answer is simple. Don't. It seems to me that over-planning is not good for the creative process. The characters will come to life and make their own middle-chapters, and usually (but maybe not always) find their way to the end that you planned.
But maybe I have the wrong end of the stick here. I am talking about fiction - a story that you make up. I'm sure you would need to put more detailed planning into a non-fiction or self-help type book.
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