I spent most of an evening pawing through the mess of notes I’d accumulated for the outline to the last third or so of Always Outnumbered, Never Outgunned, and tried to pull it together into something like an actual outline instead of just pages and pages of freeform rambling. This is the drawback to using a wiki as an organizational system: if you don’t rigorously impose your own discipline upon the results, you will end up with that most dreaded of design patterns, the Big Ball of Mud.
The problem isn’t that there’s disorganization at some point in the process of generating this stuff. (At one point I had notes towards the end of the book scattered across three different sections of the wiki.) The problem is when you're not able to impose discipline on the results, and for a few days I stared and stared at this Big Ball of Mud and couldn't figure out why I wasn't able to pull it together. Finally, I opened a new section in the wiki, and after about an hour of judicious copying and pasting, I had a bullet-point outline assembled from the mess of notes I'd made. What had been so difficult about that?
Over lunch the next day — homemade seafood salad on a bagel, tomato soup, garic & herb Triscuits — it dawned on me. It wasn't the work I was shying away from doing. It was the fear of burying things, of having stuff that needed to have a place somewhere in the final manuscript gets inadvertently shelved or drawered in the process.
I have a partial workaround for this. One entire section of the wiki is explicitly labeled "To do in next draft." In there I place everything that I know I haven't included yet in the story, but which I can iterate through while writing the next draft and find places for. If something doesn't make the cut, I mark it and move on. I've used such a scheme successfully for several books running now.
So where did this fear come from? I have a few theories.
When my wife and I moved from New York to Florida three years ago, we both rid ourselves of a great deal. In both of our cases, we let go of at least two-thirds of our respective book collections. (Avid readers are drawn to each other like unpaired hydrogen atoms.) At first the whole thing seemed daunting, but as we sifted and sorted and triaged, the process became speedier, self-fulfilling even. By the time we settled into our new house, we'd both established the idea that we should do something like this periodically, to avoid drowning in things we'd only read once and might not likely ever return to again. Of all the things we gave away, I ended up actually regretting only two or three of them going missing. In other words, it wasn't the actual parting with the books that was the problem, but our anticipated reactions to that — worrying about future regret that turned out mostly to be hypothetical if not downright fictitious.
This applies, too, to the things you collect in anticipation of adding to your project. Ideas for scenes, snippets of dialogue, insights that you write down in an abstract way and tell yourself you're going to find a concrete embodiment for later. Write down enough of it, and after a while all of it seems appealing. You worry that leaving any of it behind, even if deliberately, will amount to a hole in your work.
Then you worry about leaving behind things that might have become buried somewhere in a part of the wiki that you haven't set eyes on lately. Out of sight, out of mind, right? And so you worry that any attempt to pull things together will just become a never-ending spiral of being unable to decide what stays and what goes.
This fear breeds in dark corners, and so the only solution is to shine light on it — to pull together that list, to decide what stays and what goes, and to cut your creative losses and move on.
Ambitious authors all have, at some point or other, the feeling that they can reflect all of existence in some work of theirs or other. Or that the work in question is meant to do that, and they are somehow falling short of the task. Settle for something imperfect but tangible — a manifestation of the process, rather than an attempt to create a changeless artifact outside of it — and you go a long way towards not intimidating yourself. Then you can trade up the ambition to Make It for the aspiration to just Make Something.