I have a pretty fraught relationship with my todos. On one hand I consider myself fairly organized and (at least according to a personality test) like making lists. On the other hand I never seemed to have figured out a system which really worked for me. I bounced from system to system and software to software.
That is — until my friend John O’Duinn recommended reading “Time Management for System Administrators”. Cut out the actual system admin parts and the book presents a super-solid system for manage your working life; including a way to manage your todos which is now my default and the first system which works (for me — your mileage may vary).
Here’s how it works:
Start by writing down all your todos in a single list. Every time something new comes up, add it to the list. Each item is tagged with the expected time it takes to complete the task (for me this is 5, 10, 15, 20, 30, 45 min and 1h, 2h, 3h — any task beyond 3 hours feels like something which needs breaking up) and a tag marking the importance (A — needs to be done today; B — needs to be done soon; C — everything else).
At the beginning of each day go through your calendar and look how much time you have outside of meetings (for me this can be as little as literally zero and typically no more than 4 hours — yes, I spend a lot of time in meetings and with other people). Then go through your todos, first taking all the As (as they need to be done today), adding up the time it will take you to complete them — and then adding Bs and eventually Cs until your time budget is full.
The last step is to transfer your todos into your calendar, blocking time off for each todo. Now your calendar tells you exactly what you should be working on at any given moment. As you go through your day, new todos end up on your master list the moment they show up.
The software I use (and love) to manage this process is TaskPaper on MacOS — a super-simple, flexible text-based todo list manager. Given how simple the system is, you can pretty much do this with any software or on paper (if you prefer analog).
If you’re struggling with your todo list — give this system a try, it works wonders for me.