Unhelpful ways to think about try/fail cycles and stakes

You might have heard of the idea of obstacles in fiction. If not the general idea is to write something into your story that prevents your character from getting what they want. The thing that prevents them from getting what they want is called an obstacle. If you have ever written a story, you have probably written one – congratulations! Two closely related ideas are the try/fail cycle and stakes. In the context of the try/fail cycle, the protagonist is supposed to try to "overcome" the obstacle, and fail, or succeed but at a cost.

I've run into several ways to misunderstand these ideas. Misunderstanding them has made it harder to think through scene ideas. Here are three such misunderstandings. At a high level, they are: (1) Overcoming doesn't mean obliterating, (2) you have to make things worse when they fail, and (3) the most important thing is not whether they succeed, it's the consequences of their actions.

One misunderstanding: The obstacle doesn't have to "go away" even if your character succeeds at overcoming it! Some examples:

1. Say your character is trying to convince a bouncer to let them into a nightclub. The bouncer doesn't want to let them in (obstacle). They bargain for a while and eventually succeed in convincing the bouncer to let them in. Later on in the night, they're a bit too drunk and get into a fight. The bouncer throws them out and won't let them back in.
2. You're writing an adventure story. Your protagonist is searching for treasure in a dungeon (their goal) but they run into an aggressive kobold sniffing around for food (obstacle). They scare the kobold away with a stick, overcoming the obstacle. They search the room, and after some difficulties find and open the treasure. But later, after they find the treasure, the kobold comes back with fifty friends armed and ready for war. (I'm pretty sure I've seen this pattern before in a TV show or a movie, though I couldn't say what it was. It sounds like the kind of thing that would have happened on The Mandalorian but who knows.)
3. Your protagonist is doing action movie things and stomping around on rooftops. They need to get to another building to get away from The Bad Guys. Unfortunately, they're afraid of heights (obstacle). They are able to work around this by closing their eyes (overcome!). But before long the bad guys catch up and start shooting – and now they have to open their eyes and pay attention to where the bad guys are shooting (from) so they don't get shot. Now the fear of heights is back.

Another misunderstanding: Failure is not enough. If your character "just" fails, there is literally nothing stopping them from doing the same thing again. That's boring for the writer and boring for the reader. We have to make things worse.

But do we really? The character could just decide at some point to try something different. People do sometimes. Why not let them do that? Why do we have to make things worse? I think the answer is: Because it makes for a better story. It forces them to do something they wouldn't normally do. The first thing they try is probably the first thing they always try. Likewise the second and the third. They're doing what they normally do, which is probably par for the character – it's what you'd expect them to do. You need the pressure to force them to do something unusual – to force them to surprise you (and the reader).

A third way to misunderstand: The important thing about this process – the character wanting something and trying to get it – is not necessarily whether they succeed or fail. It's what happens as a consequence of the way they try to overcome the obstacle. I originally learned this one through one of Ellen Brock's videos. Max Florschutz put a similar idea in his post on the try/fail cycle (calling this "the evolving story"), which I probably read around the time it was posted, so I guess I didn't quite get it the first time.

To steal an example from a movie, maybe your character is a burglar. They break into a well-guarded house, they find the vault, and after some difficulty with the lock crack it open using cold nitrogen. Except what's in the vault is junk, just an old motorcycle suit – the burglary is a bust. They make a clean getaway with the trash. The burglar fails to get the money they were after, though they succeed at opening the vault and making off with its contents. But, hey, it turns out the motorcycle suit is actually a sci-fi contraption that lets the wearer grow or shrink at will...

Or, making up an example, maybe your character is a cat burglar. They've got the opportunity of a lifetime: They're going to break into some reclusive rich person's house and steal their expensive shit. And they do! They round up a whole sack of jewelry with no one the wiser. Except, while they're creeping through the vents, they witness a grisly murder – someone has killed the rich person! And on their way out, they're spotted. They're able to hide the jewels, but not themself... you could extend this example easily, either it's a cop and there is direct pressure or it's not and there is the pressure of blackmail or the possibility thereof, so maybe the protagonist goes and tracks down the witness, who convinces them (as much as the protagonist convinces themself) to testify against the murderer... you get the idea.

(I wanted to fit another burglar example in, but decided against it. It would be a good meme, but I don't think it actually illustrates the point well because Dennis Leary fails to burgle the house, and the consequences of that failure do in fact lead to the rest of the movie.)

So there you go, three misunderstandings. Overcoming the obstacle doesn't mean "getting rid of it." Failure has to push your character to desperate action. But the most important consequence of a cycle may not be whether they succeed or fail – it may be incidental to their schemes. Hopefully recognizing these confusions makes thinking about stories easier. If not... there are probably more I haven't yet learned about or that I've forgotten.