Hello! Do you have any advice for how to proceed when you have an outline, and go to make it more detailed or do some writing from it, and suddenly the "how" and "why" of a plot point that sounded reasonable when summarized briefly just aren't working out when you look at it more closely?
Absolutely. I think every writer hits this Buyer's Remorse-ish thing occasionally, and it's deeply annoying when it happens.
What's worked for me in the past has been (first) to just sit with the issue for a little. Once the realization of something-not-working has turned up, don't get in a fight with it right away! Go forward and do some writing on which you're not having any conflicts. Give the suddenly-annoying thing, or things, a few days or a week to settle down.
Then revisit the troublesome issue and see if it's calmed down at all. If it has, and seems less troublesome now, fine: just go on as you were. This kind of sudden flash of uncertainty or dissatisfaction isn't at all uncommon. They can come and go with great speed.
But it it hasn't calmed down or gone away, and is still kicking up a stink, the best way to get through the difficulty seems to be to make it explain itself.
You do this by putting your Editor Hat on—every writer has one—and writing an editorial-style note to yourself; explaining, in detail, what seems not to be working about the plot point or piece of character business or whatever: and why. Don't be curt or brief with yourself; lay it all out in detail, as if your potential note-reader had no idea at all what was going on. And tell yourself exactly what's bothering you about it. Can't work this issue out immediately? Take a day or so off and do other things, and then come back to it. The ability of the Writer Brain to keep worrying away at stuff in the background while you're doing other things is a never-ending wonder.
My experience with this approach has typically had one of two results. While writing the note (or while considering it, completed, later) I've routinely started seeing ways to fix the thing that seemed wrong. Sometimes the insight has taken a day or two to materialize after writing the note. The plain-language clarification of the details of the issue often seems to help suggest ways around or through them: or to lay increasingly open a sense of what the problem really is, so that a way through it starts becoming clearer.
...At which point you take your own advice: get in under the hood of your plot and start tinkering with the things that you feel you can fix to resolve the problem. (And it's okay to have to flail around a little among the opportunities at this point before finding the fix that works best. Try one and see how it settles in: if it doesn't, pull it out, shove something similar-but-different into the opening and see how that works.)
Or alternately: while writing that note, I've started feeling that the problem in question wasn't actually one that needed to be solved at all—that the original concept was just fine as it was. (This realization has routinely started to betray itself when writing the note about "what's wrong" starts becoming difficult because the reasons I was being bothered by turned out to be just unfocused "plotting anxiety" and weren't really all that problematic to start with.) ...At which point you file your note away (because who knows when you might need it for the resolution of some other problem?) and get on with the work at hand.
I've found this approach pretty useful. In a lot of years of work, I've only ever had to sit down and write a second note about an issue once, and that one cleared things up really conclusively. (It revealed something crucial that I'd been failing to deal with, and eventually required the insertion of a smoked-lamb,-potted-goose-and-white-bean casserole into a key chapter of The Door Into Sunset—a fabulous recipe that turned out to have a lot more in it than fiber. And which I'll post over at the Food and Cooking of the Middle Kingdoms site sometime in the next month or so.)
So I very much recommend this approach. Give it a shot and see how it works for you. Trust yourself.
And thanks for the question!
