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Transcript for Episode 10.29

Writing Excuses 10.29: Why Should My Characters Fail Spectacularly?


Key points: Middles are usually about failures. Struggling and failing, then succeeding is satisfying. Spectacular failures build sympathy. Try-fail cycles, but consider yes-but or no-and. Yes, success, BUT now things are more complicated or no, failure, AND there’s this other little twist… Things get worse! Start with your ending and mirror that into earlier events. Try-fail cycles should prepare you for the ending, and are related to the goals from the beginning. Be careful about checklist mentality, always doing three try-fail cycles. Stories should feel organic, so use the tools to assess and fix problems, not as straightjackets for your stories. Make your try-fail cycles do more than one thing. Beware plot bloat, with conflicts adding complications — make sure your conflicts are related to the central story you are telling.

[Mary] Season 10, Episode 29.
[Brandon] This is Writing Excuses, Why Should My Characters Fail Spectacularly?
[Howard] 15 minutes long.
[Mary] Because you’re in a hurry.
[Dan] And we’re not that smart.
[Brandon] I’m Brandon.
[Howard] I’m Howard.
[Mary] I’m Mary.
[Dan] And I’m going to fail spectacularly.
[Brandon] Well, you…
[Howard] Except he got it right.
[Brandon] He got it right.
[Dan] Dang it.
[Mary] Well, he was supposed to say his name, so no, that was a fail.
[Dan] Aha!
[Brandon] Okay. There you go. It was spectacular, because Dan…
[Howard] But the one time I waited for him to make a joke and he didn’t make a joke, it was disastrous.
[Mary] Well. So, point being?

[Brandon] Point being, spectacular failures. We’re talking… This is our second podcast on middles. The middle is sometimes the hardest part of the book, at least for me, the middle’s the hardest part of the book. Because there’s… I’m really excited about my beginning, I’ve got it in my head, and for me, endings, I know how to do my endings. Endings are my thing. Middles are like, “What do I do with all the space?” The answer is usually, it’s time to fail.
[Mary] One of the things that we see a a lot is that the character is going along and they try something and it succeeds and then they try something else and it succeeds and they try something else and it succeeds, and the story is over and you’re like, “Why was that not satisfying, because my character was so successful?” One of the things that we like when we see a character is to watch them struggle, because then it feels like they have earned their achievement.
[Brandon] Yes. The spectacular part of this I stole from Terry Rossio, I’ve mentioned him before on the podcasts. One of my favorite screenwriters who writes about writing. He talks about spectacular failure as one of the prime ways to build sympathy for a character. Which is great. When you can use… This is basically a plotting podcast, but when you can use plotting to characterize, you’re doing something right. He uses the beginning of Indiana Jones, which again, I’ve talked about I believe on the podcast, this opening where Indiana, the first movie, he ends up failing. He goes through this whole thing, you remember, the big thing with the boulder and the tarantulas and at the end, he gets the idol stolen from him. But he failed spectacularly, he was so awesome throughout all of that, that as you’re watching, you’re like, “This guy is highly competent, he’s highly interesting, he’s funny, and… He wasn’t good enough. I love him!”
[Mary] Some of the things that I see what I’m looking at that are that he is… He’s making the smartest decision that he can make with the information and resources that he has available.
[Brandon] Exactly.
[Mary] Then when things go wrong, it is as a direct consequence of an action that he takes, but it’s not necessarily something that he could have foreseen.
[Brandon] One of the things I like about this also is that he’s using kind of your yes-but, no-and. If you look at that opening sequence, there’s a whole lot of yes-but’s followed by a no-and at the end. Yes-but, does he get across the hole? Yes, he gets across the pit, but spiders are all over him. Does he get the idol off of the stand? Yes, he gets the idol off the stand, but a giant boulder is chasing him. Does he get away from the boulder? Yes, but now the bad guys are here. Does he defeat them? No, and they take his idol.

[Howard] One of the things that makes Indiana Jones such a great example… When I’m stuck in the middle, and I’m trying to build a try-fail cycle, one of the first things that I look at is what is the awesome ending I have in mind? What is the protagonist going to do, how is it going to work out? I mean, we’re going to win. How can I take that and mirror that into an event earlier in the story? If you look at Indiana Jones throughout that movie, well, let’s start with the end. His goal… The end in mind is to get the thing back to the museum. Okay? The actual end result is the government takes it. So in the end, it’s failure. If you look at what he does throughout the film, every time he tries to take control of the Ark, something gets in the way, he fails, somebody takes it away from him, until right at the very end, his objective becomes “Don’t look at the Ark, stay alive.” I’m pretty sure that when they started the movie, they had that in mind at the end. The movie is satisfying because throughout it, he’s taking heroic action and failing. At the end, even though his heroic action fails, he makes the decision that succeeds and the bad guys get theirs and it’s really satisfying.
[Dan] That’s a really good thing to point out is that, and it goes right back to what Mary was saying, that all these, what these try-fail cycles are doing is setting up your ending. The book that I just turned in, I was… I wanted to give it this kind of noirish ending that was actually a failure, blah, blah, and the book just hadn’t been built that way, the way that Indiana Jones is. So it felt incredibly unsatisfying to have that, because the try-fail cycles throughout had not properly prepared you for it.

[Brandon] Another way that these can prepare you, I was thinking, as Howard was saying, was that a really good book often mirrors these try-fail cycles with the failures in the middle coming back to a moment at the end that is a success. This is really important for the try-fail cycle. I think this is something that newer writers may miss. They may be like, “Oh, I need to have them fail, so I’ll have them fail this way, this way, this way.” Great, but I feel that really powerful plots will show failure that is mirrored by the ending being a success.
[Mary] Related to that, it’s that the things that they are trying and failing on are related to the goals that we set up at the beginning.
[Brandon] I’ve got a good example of this. Star Wars, the original Star Wars. We get to see Luke not trusting in the Force. He has a fail cycle. It’s a very little one, but he’s sitting on the Millennium Falcon, practicing with the little things shooting lasers at him and he’s not willing to trust in the Force and he gets shot. This whole do I trust in the Force or not becomes a theme through the movie till the end where he turns off his targeting computer and trusts in the Force. His success becomes trusting in the Force and then he’s able… When he blows up the Death Star, we’re like, “Yes. He earned that.” Because the whole movie, he’s been building to this moment.
[Howard] It may seem silly, but the first time I saw the movie and Ben’s voice comes to Luke and says, “Use the Force,” I got chills. They set that up just right. I did not realize that the Force could let Ben talk from beyond the grave. I did not realize that the Force was going to let Luke do this aiming. But it all makes perfect sense.
[Brandon] It’s also… I mean, I love the structure of Star Wars, which I… Maybe it’s a little off-topic, but the first time we’re talking with Ben, he makes the comparison, technology versus the Force, with the light saber. Here’s a blaster, it’s unwieldy or whatever. It’s…
[Dan] Clumsy.
[Brandon] Clumsy. And here is the light saber, which represents the Force. It is elegant. That’s the choice you’re going to have to make, Luke.

[Brandon] Let’s go ahead and stop for our book of the week. Dan, you have our book of the week this week.
[Dan] That is absolutely correct. The book of the week is The Edge of the World by Kevin J. Anderson. It is book one in his Terra Incognita series. I can honestly say this is the best Kevin J. Anderson book I’ve ever read. It is fantasy set in a seafaring civilization, so it’s kind of… Think Game of Thrones meets Jason and the Argonauts. Lots of sea monsters, sword and sorcery, very cool questing stuff, and of course…
[Mary] And everyone dies.
[Dan] Well, not that aspect of Game of Thrones.
[Howard] That would be Jason and the Thrones. He’s talking about Game of Argonauts.
[Dan] Game of Argonauts. The… It’s two rival kingdoms that are locked in a war, and they’re trying to destroy each other, and meanwhile they have to find this map and then find this island and all this stuff. It’s very cool stuff. Kevin being Kevin, it is full of try-fail cycles and great little narrative twists and stuff, so… It is read by Scott Brick. You can get a free copy of it at We have a 30-day free trial you can sign up for and get a free copy of this or any other audiobook.

[Brandon] Excellent. Now, the first time I was introduced to try-fail cycles, it was actually when I was taking the class from Dave Wolverton that Dan and I both took in college. Dave got up and introduced this idea of try-fail cycles. He said that he always makes something… Someone fail three times before they succeed. He actually checks it off on a list. Do you guys do that? What do you think?
[Dan] I actually, because of that same class, I was sticking with the three times and assumed that that was some kind of ineffable law. Then I looked really closely at the structure of the Princess Bride. Which, to be fair, it does have a three cycle thing. You can look at the way that the Man in Black confronts the three circus performers. Those are essentially try-fail cycles. He attempts to get the Princess back, but he doesn’t with all three. But then you look at Inago’s plot line, one of arguably the most emotionally satisfying climaxes of any movie is when he finally gets his revenge. He goes through nine full try-fail cycles before he gets to that point.
[Brandon] Really? You counted that?
[Dan] I counted them all up.
[Brandon] That’s amazing.
[Dan] That’s part of why I think that’s so satisfying. Because we’ve been with him and he just keeps getting kicked in the face over and over and when he finally does it, you can’t help but cheer.

[Brandon] Excellent. Now, can we go the other direction? Are there times when you want fewer?
[Mary] Yeah. Absolutely. One of the things is sometimes I can tell that the author is going down a checklist. For those, it’s with… When I’m like, “Oh, he didn’t really need that try-fail cycle” is when the character is making a decision that is either unnecessary or foolish, and you can see that the author is doing it because they need one more try-fail cycle.
[Brandon] This is my big worry with try-fail cycles. I, like Dan…
[Howard] The way I use it, I know that the characters need to fail and I write it so that it’s interesting and so that I’m having fun. If at some point as I’m reading, re-reading, going back, I feel like something’s missing, I will count. I will check and see has there been… not been enough of this? Honestly, that the way I use a lot of these sorts of rules, is that when I’m stuck, then I will go to the checklist and see if “Oh, am I one fail short, am I… Did he not try hard enough? What’s… Did this not mirror the ending?”
[Brandon] No, that’s perfect. That’s exactly what I think people need to hear, because we talk… I’ve mentioned this, we talk a lot on the podcast about do this, do this, do this. But these are tools that a lot of times I’m using to assess the story I’m already writing, when I feel like something is going wrong. I feel that personally, as an outliner, one of my big dangers is the checklist mentality. When I read an outliner’s book, whenever… When it fails, for me, it’s almost always because of this checklist sort of feel. It starts to feel like the story is not organic, that it is… You can see the structure, because they’re trying too hard to pay… To just follow the structure. So I think this is where every outliner needs to practice their pantsing and learn from the pantsing, and when to let a story move by instinct a little bit more than by the strict number of things on your outline.
[Dan] The other thing that you can do to help make sure that your try-fail cycles don’t feel forced is to make sure that they’re accomplishing more than one thing. So that you can’t, like Mary said, read it and go, “Oh, try-fail cycle number three.” A wonderful example of this comes from Jaws. Early in the movie, they catch a shark, but it’s the wrong one. So there’s a try-fail, but the other thing that scene is doing is setting up in the audience’s mind what a shark looks like. We’ve seen it, it’s dead, it’s small, it’s not threatening. So when the actual shark shows up, we’ve been trained to be terrified by it because it exceeds our expectations.

[Howard] At risk of drilling into a project I’m currently in the middle of, when we designed the Planet Mercenary role-playing game, I wanted to make sure that this was a role-playing game that had try-fail cycles in it. So we created a deck of cards that… The original name of the deck was yes-but. In which, depending on the dice rolls, about 25% of the time you would need to draw a card. The cards were things like, and I’m going to read one here. “Best Concussion Ever. The last player character who took damage may transfer one skilled point from one skill to any other skill.”
[Howard] Okay. What this does… Okay, you succeeded, but something else happened. Something else has gone sideways. Some of these are a direct result of what you’ve done…
[Brandon] Oh, that’s awesome.
[Howard] Some of these are just really terrible, terrible things you don’t want to have happen. But we built the whole game around the idea that if you own the failure, if you make it spectacular, the group storytelling experience will be more fun. As Alan play tested this with his role players, they came back and they said that this was amazing. This was like reading good novels. Which brings it all back around. If we… If you’ve got a good try-fail cycle, it’s a good story.

[Dan] So let’s go back to Princess Bride again. One of the great things about that, I mentioned that the Man in Black defeating those three circus performers, those are try-fail cycles. But narratively, they are all successes. I mean, that’s one of the greatest swordfights ever. That’s one of the greatest outwitting dialogue scenes ever.
[Brandon] This is your Princess is in another castle.
[Howard] They are fail cycles, try-fail cycles for Vizzini’s team. It’s a failure for people we like.
[Mary] So the thing is, about the Man in Black defeating Inoya Montoya is that how many try-fail cycles you can have on any given problem, I think is directly related to how important that problem is to the main character. If it’s something that’s fairly trivial to the main character…
[Brandon] Right. That’s a good point.
[Mary] And you have 15 try-fail cycles around it, you’re going to drive your readers crazy. But you can have 15 try-fail cycles on getting the Princess out of the castle if that’s the driving motivation for the whole thing.
[Brandon] I think that’s perfect. That’s a really good thing to keep in mind. I also like what Howard said, which is you gotta remember your yes-buts in your try-fail cycles. In fact, depending on the story you’re telling… A lot of thrillers, their pacing is all yes-buts. Yes, we achieve this, but we made it worse. Yes, we achieve this, but we made it worse. Rather than the Indiana Jones no, I failed, and I got kicked in the head. So I think taking all these tools and looking at what they’re trying to do, which is prove to the reader that this task is difficult, prove to the reader that hey, our characters are trying, really capable, competent, interesting, intelligent things, and it’s still not working. This must be a big problem! That’s your goal.
[Mary] There’s one caution that I want to put in here when you’re doing these yes-but, no-and’s or try-fail cycles. It is that you want to watch out for plot bloat, which is that when you are introducing these conflicts that you do want to make sure that they are related to the central story that you are trying to tell. Because it’s very easy to cause a complication for your character that opens up a whole new plot.
[Howard] We had to put… In the game, we had to create a mechanic where the Game Master can buy that card off and say, “Nope. That doesn’t happen.” Because it bloats.

[Brandon] We are out of time. We will talk more on this topic in upcoming podcasts, where we dig into pacing. But for right now, Mary has homework for you.
[Mary] Yes. So we are going to play with the yes-but, no-and try-fail cycle. What I want you to do is to look at the next conflict your character is facing and just think of the smartest thing they can do. Then start a yes-but, no-and cycle. Just for purposes of exercise, try it as a three cycle. So they’re going to fail twice before they succeed. You can decide if they… If you have two yes-buts or a yes-but and a no-and. But each time they try, that thing needs to get worse.
[Brandon] Excellent. This has been Writing Excuses. You’re out of excuses. Now go write.