Just so you know: I haven't quite got this one figured out yet, thus the designation "rumination" rather than, say, "revelation". Some systems take a little longer than others to get going, and that's okay. Experimenting and searching for answers is just part of the Quest.
As always, I'd love to hear about your experiences in this regard, if you've found something that works particularly well--or not--and why. I have a feeling that to-do lists are the most idiosyncratic of the four classic organizer modules, and thus, the more the merrier in terms of tips, tricks, techniques and strategies. What doesn't work for one person for a particular reason may be the exact reason why it works for somebody else. The important thing is to keep trying and experimenting until something clicks.
That said, here are a few considerations:
Format: Blank or Pre-Printed Pages, and Does it Matter?
I used to write my lists on blank typing paper, finding most pre-printed to-do lists too constrictive for my handwriting and for my list-making style. I've since turned to Levenger's letter-sized Things To Do page, which allots two lines per entry and a has nice big box for checking items off. The separate column to note an item's "Priority" is all the structure I need, and the classy white-and-French gray color scheme has transformed list-making--something I used to dread--into a joy.
To Schedule or Not To Schedule?
Should you put To-Do's unrelated to a particular time, day, or date on your calendar? Productivity guru David Allen says no; celebrity organizer Regina Leeds says yes. Allen's argument is that it's pointless to schedule things that can be done any time and that it just junks up your calendar. Leeds' argument is that if things don't get scheduled they don't get done. I can see both points. I've decided to adapt the priority approach: while I'll save most of my calendar entries for date-specific events, occasionally I'll decide on The One Thing That Needs To Happen Today and put it on my calendar, even though the task is not date-specific, technically speaking. This keeps my calendar relatively clear while helping ensure priorities get done.
Minimal Approach or Everything-But-The-Kitchen-Sink?
Allen prescribes the Everything-But-The-Kitchen-Sink approach to task lists, in which you write down every single thing you can think you might possibly ever need to do. In this approach, sixty, seventy tasks are the minimal norm; hundreds of tasks are not unheard of. I'm more a minimalist here; I do okay with a single side of a page's worth of tasks--about 18 or 19 items using Levenger's Things To Do page. Anything more tends to overwhelm me.
One List or Multiple Lists?
I'd never considered keeping multiple to-do lists until I read Allen's Getting Things Done. Allen keeps lists by what he calls the "contexts" in which they occur, i.e. "at computer" for things that can be done online, "at home," "at office," "calls," "errands," etc.
In the past, I structured my to-do's by using category headings not unlike Allen's contexts. I've since developed separate to-do pages for "Projects," "Friends/Family," and "Blog."
The road has been bumpy on this one; while such lists are indeed useful for identifying topic-specific to-do's, I find I don't like writing the initial lists in this way. This is where digital organizers come in handy: you can write out your day's list and just assign a tag, a label, or a category for each of your to-do's, which are then automatically associated with the lists you designate. Old fashioned pen-and-paper users have to work a little harder here to figure out their system. I find I like to start with a fresh list each day--what I call my "active list" rather than add to an on-going list from the get-go. Theoretically, any items that aren't finished by the end of the day get transferred to the appropriate category-specific list, but I still have problems capturing everything on those specific lists. I also find that once relegated to a specific list, tasks tend to stagnate.