I plan by making lists. What to do today, tomorrow. To do lists for the house, the yard. What to pack, what to buy, what to eat. And it is so funny because we make all of these plans right? But hardly any of them turn out the way we expect! One of the most entertaining things you can do for yourself is start keeping track of your lists. My husband and I just use a plain old notebook and take notes, make lists etc in that so we can go back and see what we have written down and see just how smoothly things went.
The worst habit I have when it comes to lists is making one (especially the grocery list) then not utilizing it at all.