Planning is Hard in the sense its takes a lot of time but all you have is a list of things to do and if your lucky maybe a basic mind-map to show for. I've just finished planning and organizing for some personal projects and it ate up 9:30am to 2:30pm spend most of my time planning and organizing my old notes. If you want to have it all, you gotta have a plan and you have to have really achievable goals, even if its underwhelming by personal standards.
Anyway, in my min-maxing plans I realized that there is really a hard limit to how much productivity and originality you can squeeze out in a day. It helps when I have a day job, because finding small wins at work also contributes to over-all morale (and I'm speaking like work is not my 1st priority; human after all). Because I've hit the diminishing returns of my productivity, the only source of "time" and "energy" I can find is by making a lot of my note-taking and planning mobile. That means using my phones' built in recorder and do a lot of things using route memory. Traffic in Metro Manila is about 1 hour one way, to most of my destinations.
I'm one of those guys who has to talk about an idea to really be able to scrutinize and visualize it. Its really weird, I only get more ideas if i have someone to bounce more ideas to even if monopolize the entire conversation (which is kind of being a jerk). Maybe its another psychological artifact of growing up gamer. I'm not the type to abuse friendships in that way, so I'd rather pay someone to listen to my ideas and not sacrifice any social capital having someone bear my pedantry.
So the best kind of planning I can do is while on the phone, speaking to someone who is taking notes and organizing my thoughts into a chart or list of some kind. The Visualization of Ideas in that basic graphic form always helps me think, even if its so hard to prove how useful it is. The plan is that as I continue to work out the details, I can then create a structure to follow. The structure helps me find when I can proceed and know when its most economical for me to stop and proceed to the next phase. All the writing I will be needing does follow a kind of structural formula, answering a list of questions and details needed by the reader.
So I have a prospective Personal Gaming Assistant now. Before I start making a serious financial commitment I'll be spending the month organizing my notes and seriously looking at the projects I've lined up. Using what I learned in work to make conservative predictions at the cost-benefit of such an attempt. Hope it works out, anyway, worse-case scenario I'll post my post-mortem so that other GMs can build over what I learned (i hope they share what they learned).