I think you ought to investigate different approaches to keeping organized (there are many) and pick one that speaks to you, and then choose the organizer/planner that fits your style. Otherwise, you may be trying to force yourself to keep organized in a way that is frustrating and likely to fail.
Here is an article I read recently about organizers:
http://www.lifehack.org/articles/productivity/10-great-notebooks-productive-people-love.html . Lots of people really love those moleskein spiral binders; I think it's a "Getting Things Done" habit, but I'm not sure.
The whole Lifehack website is good for organization tips without being too dogmatic about any one style. There's also a site called 43Folders (or 49Folders or something like that) that's good. (EDIT: Here's the hipster PDA at 43Folders:
http://www.43folders.com/2004/09/03/introducing-the-hipster-pda).
My own method is to use Outlook to the max -- contacts, calendar, dated task lists, color coding, category tagging, etc. I carry a Blackberry at all times (although other devices would work) and everything gets plugged into Outlook immediately. I try to minimize paper because I just lose it or forget to enter the data later (although I carry some paper to catch stray thoughts if using the BB is not feasible). I also use lots of Google Apps to coordinate with my partner -- Google Docs and Google Notebook are especially good. Google Docs is a file cabinet of things we both access and add input to, such as our running grocery list and our budget, and you can access it on-the-go from the Blackberry or most other smartphones. Google Notebook is good for catching and storing random thoughts and keeping them organized. Lots of other good Google Apps also make sense but I have not learned how to use them well enough yet to incorporate them.
Until you decide what's right for you, try the "hipster PDA" to get a feel for what you like/dislike.
Good luck!