Thank you so much for taking the time to write such a thorough response! There are so many good points here that I'm definitely taking notes. I have a handful of follow up questions if you don't mind.

Would you be willing to share an example with me of what your status reports and timelines look like and how you organize those? Not sure if it would be too specific to your job but I would love to see how you outline things. At my last job I had to submit a report on where I was at with projects and how my next week would be spent but it would literally take me hours to put it together even when my boss said it was a 15 minute task. But I could never figure out how to quantity so many projects so simply.

You said you sometimes have as many as 25-30 tasks. There is not enough time in a week for you to "touch" each one so how are you breaking down your calendar? Even if you have a team working on a lot of those you are still managing them which means you are still receiving emails and needing to track progress. How do you do that?

I absolutely need to work on being honest with myself about how much time tasks will take. This is very difficult for me for some reason. I always assume it will take less time so I don't give myself enough.

Your last point about pushing deadlines is a really good one. I'm going to keep that one top of mind.