Where I rant about TODO lists falling short

TODO lists never seem to work for me. I’ve tried most of them from OmniFocus to the Bullet Journal to scheduling every moment of every day on a calendar. Between my work at BA3, side projects, CocoaHeads and CocoaHeads.tv, and just normal home tasks; I struggle with this daily. This afternoon I decided to try another brand of TODO list, Remember the Milk and I think I realized why I don’t stick with it.

I think that for productivity software to work at scale or consistently over time, you have to trust it. It has to do what you expect and it has to provide you with the information you need. This is extremely important when it comes to a TODO list. To really unload your mind from all the different tasks, you need capture those things in a list with some priority and some time frame. When dealing with specific things like “Call Mom on Tuesday” or “Schedule Doctor Appointment”, it works well. As things get bigger it does not.

As a contrived example, let’s add a TODO item for “Add sign in screen to app” with a due date of next Friday. That’s great, it’s recorded and you can move on. The problem comes back to trust. I want my todo list to tell me what I should be doing right now. So I move on happily doing my tasks until next Friday comes along. Then I hit the problem, it will take me two days to do this! I’ll never be done in time! This introduces lack of trust for the system and I end up trying to remember what I need to do.

Obviously I could break up the task into smaller portions, and some apps have subtasks that you can set up. I think what I really need is the ability to add a task and an estimate so that it tells me days ahead of time to work on that larger task. It would almost be a recurring task but tied to the tasks deadline. I can mark off that I worked on it today, and then still be reminded to work on it tomorrow.

How do you track TODO items for bigger tasks? Do you break it up into small peices that can be assigned to multiple days, do you make tasks recurring until they are due, or do you just wing it? I’m really curious how others do this so let me know on Twitter.