I’m completely with you, Leah. When there is no pressure of a deadline or if I don’t structure my day, I flounder as well.
As for prioritizing, I put whatever deadline is coming up the fastest first. For example, I put out a blog post at least three days a week. So, on those days, that’s one of my MIT. With my newsletter, I devote one day a week to working ahead on content. With deadlines that are in the distance (like working on self-publishing my first book), I make sure I look at my working plan and then hammer out what is up next on my checklist.
When I’m working with my teachers in my buildings, I usually have three deadlines with each task they need to complete. However, they don’t know this. They think the first one is the actual deadline, but I always build in a cushion for the stragglers. I think what helps is that we look at everything we do as benefitting our students when we’re getting things done on time.