I'm constantly trying to keep my various projects organized--for clients, for myself, for people I hire on a per-project basis. In the world of distributed work in which I live, I might at any one time have a half-dozen people working on a host of unrelated projects with no similar geography.
Like a lot of small businesses, I don't have a scheduling assistant (except my PalmPilot) or anything resembling a secretary to tell me who owes me what at what time or what the deadlines are. To some extent, I solve the problem by working with only reliable people who are honest about what they can and can't accomplish.
I also use Microsoft Excel spreadsheets or Microsoft Word tables to track what I'm doing. I've tried the Journal function in Outlook, which tracks every move you make, but found it too cumbersome.
I have played a bit with Basecamp, a Web-based project management and document-sharing program that allows me and clients to log on to the same area and update each other. I've tried free wikis at Jot.com, and I've toyed with the idea of having my own project-managing blog (haven't done it yet). I've thought about getting Microsoft Project (which, as a professor said, is not something you need unless you're building the Hoover Dam). I've used a Gantt chart. And, just today, I saw SharePoint, a project-managing application that comes free with a Microsoft 2003 exchange server, and which I'll probably start using with one client who also has a small business and has to manage staff and a bunch of consultants, including myself, along with myriad projects.
None of them is just right. The problem with all of these is that none of them is perfect or completely intuitive. Also, none of them works unless you rigorously record every step in a codified and similar way, and none of them does a great job of "talking" to you to prompt you or tell you what you have to do next or inform you of the deadlines you've missed--as would a human project manager or a good secretary.
I don't have any great, overarching advice here--it ultimately comes down to whether you're obsessively organized or not (I'm not, really), except to say that it's worth thought and trying out, and I am happy to hear from folks about what their solutions are. I don't need to hear from vendors. (Really guys, the moment you tell me your new-new thing will solve all my woes, I'll start shutting down my brain.) But I would love to hear from users who have found solutions and can give me tips on being as lazy as possible while keeping my various "to-do" lists in check and alive efficiently. I don't care if it's a technology. I'm looking for solutions.