The Ultimate To-Do List

I have a complicated life, mostly by choice. I probably have a hundred items on my mental to-do list if you count all household, personal, and business tasks. There are so many tasks on my list that I literally don't have time to maintain the list itself.

On any given day I might have a dozen items that I need to remember to put on a shopping list, probably twenty minor home repairs that need attention, a dozen phone calls, several tax-related questions for my accountant, several questions for my attorney on the five projects he's working on, and about twenty-five files/piles on my desk that all relate to tasks I need to complete. And none of that counts my everyday tasks of writing blog posts, making comics, and approving licensed products. Nor does it count the holiday crush and the scheduled events I need to prepare for, and on and on.

I'm sure most of you have complicated lives too. So I wonder if anyone has created the ultimate to-do list system.

The biggest problem with a list, especially once it gets to a dozen items or more, is that a list is one-dimensional. Ideally, I want my list sometimes organized by priority, but other times by location. For example, my to-do list app should sense my speed and motion and sort to the top of the list any tasks that involve phone calls, under the theory that I'm probably driving my car and I can make some calls on the way.

Other times I want my to-do list sorted by location. If I'm driving past the store, the items I need from the store should sort to the top of the list automatically. That function already exists in at least one "notes" app I've seen.

At other times I want my list to have the simplest and quickest items on top because I might have a spare five minutes and want to knock off a few items.

Time-of-day matters too. For the first few hours of every day I don't want to focus on anything but creative work. After dinner, I'm more in a frame of mind to handle boring administrative stuff. I want my to-do app to know my personal preferences for managing my energy level.

I also want my app to give me some satisfying feedback for crossing off an item on the list. Crossing off items is strange fun.

At the very top of my wish list for a to-do app is speed. It's not unusual for me to think of five things to add to my list on the walk from the kitchen to the garage, but it would take nearly a minute to get my phone out and enter five items. I rarely pause for a full minute to do anything, so instead I just feel frustrated in the knowledge that I will forget two of the five items on the list.

I also want to attach long notes to any item on my to-do list. And I want my to-do list to tie into my calendar. And I want to share my to-do list with my wife in case our lists overlap or she is going to a store that has something on my list.

You can see the problem here. It would take so long to manage a list with so many features and options that the list itself would become impractical. For every item on my list I need to know. . .

1.      How important is it?
2.      How long to complete?
3.      Where is it done?
4.      What order do things have to be done?
5.      Who else might have the same task?
6.      Is it done by phone, Skype, email, text, in person, or manually?
7.      What time of day do I prefer doing it?
8.      Does it combine with other tasks at the same time?
9.      Is it complicated or simple?
10.  Is it work-related or personal?

I've tried several popular apps. None have risen to the level of a plain scrap of paper. So I'm wondering two things:

1.      How long is your typical to-do list?

2.      What is your system for managing it?