Monday H1 – 2 questions about scheduling

I love watching Lauren and Tyson talk about Monday Hour One and love the idea I will someday implement what they are saying.

My to-do list consists of 49 tasks this week, ranging from “grocery shopping” to “hire additional staff.” I categorize them in “this week” and “later.” This week’s tasks are 39 items.

Q1: The “later” always gets pushed forward. I tried earlier this year to divide them into “today,” “this week,” “this month,” and “this year,” but found myself spending hours planning, replanning when I failed to execute plans and generally being overwhelmed. How can I simplify?

Q2: The 39 items of this week are not fitting in my calendar and are too different to chunk together. (Is this true ?) I find this happens often and what I do is to go back to my paper and pencil and old to-do lists. I find the thought and idea of Monday Hour One so beautiful and tempting, but I am not succeeding at it very well. How can I fit all the small details into the digital calendar?