One thing I keep overthinking is my outline on my current story. Yes, I believe outlines can be helpful as you know what’s going to happen with the plot and when, you just have to worry about creating each chapter and making them blend. I find it’s much easier to write when you know what you’re meant to write next and since you’re the writer, you have the creative license to change whatever you want.
Ernest Hemingway would say that he always would stop writing when he knew what was coming next so he could pick up right where he left off. Your outline can help you do the same thing where you’ll know what you want to tackle the next day. Sometimes, the hard part is simply coming up with what comes next in the story, whether you’re writing the whole thing out or if you’re creating the outline.
I’m working on my current outline for a short story and I keep overloading it with detail and forgetting that the details come in the actual writing, not the outline. If there are important details that have to do with the plot and whatnot, yes I’ll include them. However, when they’re little incidental details, I need to learn to leave them out of the outline because I might as well just focus on writing the story itself. I’m in the constant struggle with my outline of not wanting to write too much and feeling lost if I write too little.