
Show notes
Today, we’re talking about the “try-fail cycle” and why failure is essential to making the middle of your story actually interesting. It allows readers to follow characters as they try something, fail, adjust, and try again until they finally succeed. Our conversation gets into how failure builds tension and empathy and how you can use “yes, but / no, and” to control your story’s momentum. We also address the difference between barriers and attempts, and how to keep things from feeling repetitive or stalled, whether you’re writing epic fantasy or a quiet coffee shop story. Homework : Look at the MICE quotient elements (milieu, inquiry, character, event) in your story and make a list of barriers for each. Then choose a smaller subset of those barriers that work well together, and use them to design try-fail cycles that keep your story dynamic without becoming repetitive or overcrowded. Locus Magazine Annual Fundraiser (ends April 14th, 2026) Join us in supporting Locus Magazine– explore the campaign and fantastic rewards for donors online at locusmag.com/igg26 . Final WXR Cruise! Our final WXR cruise sets sail for Alaska in September 2026—get your tickets here ! Credits: Your hosts for this episode were Mary Robinette Kowal, Erin Roberts, and DongWon Song. It was produced by Emma Reynolds, recorded by Marshall Carr, Jr., and mastered by Alex Jackson. Join Our Writing Community! Writing Retreats Newsletter Patreon Instagram Threads Bluesky TikTok YouTube Facebook Our Sponsors: * Check out HomeServe: https://www.homeserve.com * Check out MasterClass: https://masterclass.com/EXCUSES * Check out Talkiatry: https://Talkiatry.com/WX * If you’re struggling with OCD or unrelenting intrusive thoughts, NOCD can help. Book a free 15 minute call to get started: https://learn.nocd.com/wx Support this podcast at — https://redcircle.com/writing-excuses2130/donations Advertising Inquiries: https://redcircle.com/brands Privacy & Opt-Out: https://redcircle.com/privacy
Highlighted moments
“Yes, but is movement towards the goal, but with a consequence. And when you've got no and, it's movement away from the goal and then with a consequence.”
“a barrier is something that is between you and the goal, like maybe a literal door. Sometimes it's a priest. The try-fail cycles are the things you do to try to get through that barrier.”
“Where you run into story bloat is when the consequence is from something else.”
“if the try-fail cycle is exactly the same and the barriers are exactly the same, it feels like the character doesn't grow.”
Transcript
Writing Excuses Introduction
0:00For more than a decade, we've hosted Writing Excuses at Sea, an annual workshop and retreat on a cruise ship. You are invited to our final annual cruise, September 3rd through 11th of 2026. It's a chance to learn, connect, and grow, all while sailing along the stunning Alaskan and Canadian coast. Join us, the hosts of Writing Excuses, and spend dedicated time leveling up your writing craft.
0:31Attend classes, join small group breakout sessions, learn from instructors one-on-one during office hours, and meet with other writers from around the world. During this week-long retreat, we'll dock at three Alaskan ports, Juneau, Sitka, and Skagway, as well as Victoria, British Columbia. Use this time to write on the ship, or choose excursions that allow you to get up close and personal with glaciers, go whale-watching, learn more about the rich history of the region, and much more.
1:02This will be our grand finale after over ten years of successful retreats at sea. Whether you're a long-time alumni or a newcomer, we would love to see you on board. Learn more at writingexcuses.com slash retreats. That's writingexcuses.com slash retreats.
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3:08To get started and learn more, including important safety information, WeGovi clinical study information, and restrictions, visit ForHERS.com. If the world were like a Sleep Number mattress, everything would adapt for your comfort. Because as your life changes and your body changes, Sleep Number mattresses adapt and shift to give you personalized comfort night after night. And now everything's on sale during our Memorial Day event. Save up to $1,200 on mattresses, plus free delivery when you add a base.
3:38Ends Monday. To experience a whole new world of comfort, visit a Sleep Number store or go to sleepnumber.com. Sleep Number to a good life's sleep. If the world were like a Sleep Number mattress, everything would adapt for your comfort. Because as your life changes and your body changes, Sleep Number mattresses adapt and shift to give you personalized comfort night after night. And now everything's on sale during our Memorial Day event. Save up to $1,200 on mattresses, plus free delivery when you add a base.
4:08Ends Monday. To experience a whole new world of comfort, visit a Sleep Number store or go to sleepnumber.com. Sleep Number to a good life's sleep.
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Writing Excuses Podcast
4:48This episode of Writing Excuses has been brought to you by our listeners, patrons, and friends. If you would like to learn how to support this podcast, visit www.patreon.com slash writing excuses. Season 21, episode 14.
5:07This is Writing Excuses. Because at first, they don't succeed. Tools, not rules. For writers by writers. I'm Mary Robinette. I'm Dong Lund. I'm Erin. And we are talking about the middle again. This time we're going to talk about a different tool for working through the middle. It's something called a try-fail cycle. You know the old saying, try, try again. You know, if at first you don't succeed, try, try again. That thing. That is literally what we're talking about.
5:39A character tries something, and then they fail, and then they try it again, and they fail. And eventually they succeed, and you move on to the next problem.
5:48So your characters have goals. And in the middle, they spend a lot of time trying to achieve that goal. And then failing. So let's talk about what a try-fail cycle does for us. Kind of why we use them. And then some of the tricks. I mean, I think fundamentally failure is interesting, right? I think failure is one of the most interesting things. I'm so evil. Yes. Fail, I told you. I mean, like, I mean that in a really broad way.
6:18Like, even in my personal life, as unpleasant as it is to fail, the most important lessons I've ever learned, the most growth I've ever experienced have all come from failure, right? And so your characters also need to fail for us as the reader to understand them and to root for them, right? Competence porn can be really exciting and fun, but also at some point that needs to run into friction. Competence is useful for showing on screen to establish how bad failure is when it arrives.
6:50But in general, seeing how characters confront and overcome adversity is where we get to get into the meat of who they are, what matters to them, and why I care about the story in the first place. Also, if you want to write a really long book and they succeed really early, it's not going to – it's going to be – I mean, I guess you're going to have just like a series of increasing – like the opposite of a series of unfortunate events, like a series of fortunate successes. But eventually, like, don't you run out?
7:22I almost feel like that – it's like that old chessboard puzzle where if you put one grain of rice on the first square and then two, eventually, like, you reach the moon if you double it each day. Like, you can only succeed at so much before you, like, one life. I mean, I've read that manuscript, right? I've seen that book. And it comes from this place of wanting your heroes to be successful and continue to – just continue to achieve, right? And it's exciting as this, like, power fantasy thing, but it makes for a really flat reading experience because it just feels like you're playing Calvin Ball the whole time. And I don't know what the rules of this world are because they just get more powerful and defeat people over and over again.
7:58And it's like, okay, where are we going? Yeah. Yeah. Well, I think at the heart of it, we like to root for someone. Yeah.
8:06It's something that is – you know, it gives you an opportunity to invest. It gives you a source of tension. Like, you want them to succeed. And some of my favorite theater experiences have been when the show has been going along and then something goes wrong and the actors, like, they have to recover from that. And watching that is so cathartically satisfying. And I think this is the same thing with writing, that you want them to fail in ways that they can recover from if you are planning to write towards a happy ending, I should say, having them achieve their goals.
8:48Yeah. I do wonder if, like, is the human brain, like, baked into – like, do we want some amount of failure in life? So I think about, like, if I was telling you about somebody – maybe this is only true in, like, my gremlin heart – but if, like, I was telling you about somebody, I'm like, they are great, they're rich, they're famous, they've, like, done all the great things. And I'm like, and their marriage. I feel like everybody would be like, oh, something wrong. Be like, it's also great. And you'd be like, really? Like, there's nothing they're not doing perfectly. There's nothing that's bothering them.
9:19You know what I mean? I think this – interestingly, in an era of social media, it's interesting to see. I wonder if this will change because I think we are actually being taught more to only sort of see people at their most successful. And, like, I'm curious about the ways it may change the tri-fail cycle in fiction. Well, I mean, I think in part this is, like, where people's resentment of Nepo babies comes from, right? I mean, I think there's a lot of, like, valuable stuff in there about privilege as well. But I think the degree of the frustration is, like, the sense of, like, oh, you've always had it easy.
9:50You never had to overcome adversity, right? And I think the backlash to, you know, creators who are presented as, you know, flawless, very successful over and over again when some little crack in the armor happens, people descend on them so vociferously, I think, because of this exact impulse, right? I think there's a thing of the artificiality of presenting success at all times that when that cracks, people really just go all in right away. So I do think even though we're in this era of still needing to present success online in a certain way as an influencer or as a celebrity, that there's still that human instinct of wanting to take someone down a peg, you know?
10:31Yeah. And I think it's that and it's also the, like, the shelter dog with three legs. Like, you know, oh, my goodness, you poor thing. Or the way we will help a wild animal, like, oh, no, this pig got stuck in this barbed wire fence. We've got to rescue this pig. I love bacon. Like, you know, it's like, it's like, you know, Charlotte's Web. It's, you know, once one of the things about a failure is that it humanizes someone.
11:05Yeah, exactly. And even if they aren't human to begin with. So I think that it's important to give your characters failure. I know that I've heard people say, oh, but I don't want to, I love my characters so much, I don't want to be mean to them. I'm like, sometimes you do actually have to do that. But so I want to talk about some methods that we can use to do this, some of which we've talked about on previous podcasts, which is this idea of yes, but, no, and.
11:39So this is the idea that inherently when your character goes to try something, the reader has the question, is it going to work? And yes means movement towards whatever their goal is. No means movement away from it. Yes, but is movement towards the goal, but with a consequence. And when you've got no and, it's movement away from the goal and then with a consequence. So in the first, like, two-thirds, three-quarters of the book, you are mostly doing yes, but, no, and.
12:16And then anytime you need to switch to the characters solving the problem, then you start to give them bonus actions. So you move from yes, but, to yes, and. And I want to give, I realize this is all fairly vague, so let me give a slightly more concrete example. I'm going to use a milieu story. So milieu stories focus on thresholds. The character has to cross a threshold.
12:47When they enter the story, they cross another one when they exit. So it's basically about navigating. So if we imagine that I've got a character who's trying to reach New York for an audition. Ruby Keillor. Hmm? Ruby Keillor. Ruby Keillor. All the way to New York. Yeah, all the way. So then I look at, you know, what's stopping them? Is it a lack of funding? Is it a mechanical failure of transportation? Cultural stigma against New York? I'm not sure how to apply for a spot.
13:19Whatever it is. You know, I look at what this is. So let's say that they have to get to the airport. They have to get to their airplane. That's the first thing. It's the first threshold they have to cross. So they have to go through security. Can they go through security? No. And they realize they left their passport at home. So now can they go back and get their passport? Yes. But now they are running late and they may not make the plane. So can they get through security? Yes. But now they are even later. And are they able to get to the plane?
13:50And then when they get to the plane, it's like, yes, they can run down the thing, but the door is shut. Are they able to get on the plane? No. So there's a solid no closure there. So that's a yes, but to get to the plane. Then the next thing that I have to figure out is what happens after that. Because after they have a success or a failure, they change their tactic and then try something different.
14:18So that is where I look at this list, you know, lack of funding, mechanical failure of transportation, all of those things. And I look for the one that is kind of still keeping me in the milieu thread for this part of it. You know, all of the other things that were happening were all still like about the environment. Where you run into story bloat is when the consequence is from something else. It's like, are they able to go to New York? No, the plane is closed.
14:50And they have a cultural stigma against New York. Like, it's like, okay, well, now I have opened up this big character thing that may not have been there.
14:58But having said that, I know I'm talking a lot. No, no, no. Please. Okay. But having said that, if I only stay in a single mode, if I only stay with like one of the mice threads, it can be pretty boring, pretty predictable. Yeah. So one of the things you can do is introduce one of the other plot conflicts you're going on, because now your character has two opportunities to fail with everything that they try to do, which introduces uncertainty. It gives two things for the readers to root for.
15:29So if I say, oh, no, my character couldn't get on the plane, and instead of saying, you know, no, they couldn't get on the plane, and they're going to have to rent a car and lose money. Okay, that's still, we're still dealing with the character, the threshold. But if I said, excuse me, the milieu, but if I said, no, they couldn't get on the plane, and they have to borrow a car from their parents, and their parents don't believe in them as an actor.
16:02Now you've opened up this character thing, so what you're doing at this point is you're sacrificing one goal for the sake of another. And that can introduce a lot of interesting tension and things like that.
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16:11We're going to take a pause for a break, and we're going to come back, and I'm going to let the other two talk.
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19:51Ends Monday. To experience a whole new world of comfort, visit a Sleep Number store or go to SleepNumber.com. Sleep Number. Sleep Number to a good life's sleep. If the world were like a Sleep Number mattress, everything would adapt for your comfort. Because as your life changes and your body changes, Sleep Number mattresses adapt and shift to give you personalized comfort night after night. And now everything's on sale during our Memorial Day event. Save up to $1,200 on mattresses, plus free delivery when you add a base.
20:22Ends Monday. To experience a whole new world of comfort, visit a Sleep Number store or go to SleepNumber.com. Sleep Number. To a good life's sleep. Shop the Sherwin-Williams Memorial Day sale and get 30% off paints and stains May 15th through the 28th. Whether you're refreshing your interior or exterior, we've got the colors to bring your vision to life. And with delivery, getting everything to your door is easier than ever. Shop online to have it delivered or visit your neighborhood Sherwin-Williams store.
20:53Click the banner to learn more. Retail sales only. Some exclusions apply. See store for details. Delivery available on qualifying orders.
Writing Excuses Discussion
21:00So, hello. Welcome back from break. Erin, would you like to say something? I do. I do want to say something. And I don't know if it makes any sense, which just makes it even more exciting. But I was thinking about a four. So I love a box, just like a general. But no, I love like a four box, like in thinking about writing. And I was thinking about horror and the way that place is used. And the way that I did it was how known is this place and how safe is this place? Uh, and you can move people in horror from like, this is a known place that's safe to this is a known place that's unsafe.
21:35Somebody broke into your house. Then you like run out and you're like, oh, I went to an unknown place that appears to be safe. Wait, now that's unsafe. And so you end up playing with, and so I was, I'd never thought about like that before, that in some ways that's a way to take yes, but no, and, and see like, how can you use it on multiple, oh my God, you're showing me a box. Like, how can you make it work on these different levels at the same time? Because I think that that is a really fun way to think about it and like to extend this like way of thinking about it.
22:07Because I've also heard, my dad always talks about like writing stories with yes, but he was an English teacher. Uh, and so like, that's the way to do it. But I love this idea of adding a box. Well, it's just real small. The, the yes is, is all about momentum. And so you can control the amount of momentum a story feels like it has by whether you're giving them yeses or nos before that consequence. And I think what's really interesting is thinking about momentum. You kind of hinted to this early before the break too, but things that you can do in act one will feel very delaying in act three, right?
22:39So the try fail cycle you set up of her, like forgetting her passport and all of that. If that was an act three beat, I would be like, what are we doing? Why isn't she in New York yet? Right. Or also sort of with your grid of like known and safe, like making progress through that grid. And there also has to be an accumulation of knowledge as they begin to understand the space and the danger more. If they stay in the same place of unknown, unknown, you know what I mean? Not that that was the grid you created, but you know, they don't know what the monster is and they don't know the space. I think as time goes on, that horror movie is going to feel very flat and random.
23:13Part of it is starting to figure out what the monster is and starting to get more control over the space, right? Like, you know, then if you look at like an alien movie, it's always about understanding the creature better and then moving through the space. And really what you're doing is the audience begins to understand the space better as the character understands the monster better. Yeah. And I think like just to not to derail this entire episode into horror, like one of my favorite things to do is to take somebody into a space they believe is known. So this is the you seek sanctuary in the church or you make it to the school or somewhere that you're like, I completely understand this space.
23:49And I know the monster now I've I've made it to known and no, this is great. It known and safe. And then it's like, actually, something is wrong. The place isn't what you thought it was. The priest is the one who summoned the monster. Exactly. Like the preacher is a freaky. He's got red eyes. Oh, no. Like, you know enough to realize he's actually the villain. And I think that's where it's like really fun because you can play around with the way you're answering those questions. Yeah. Well, and the other thing is like, like, you know, with the oh, no, it's the rule of the priest. The one of the things I know I did it and and I see other people doing it is not understanding the difference between a trifle cycle and a barrier.
24:26Yes. I've been thinking about this because you were talking about this the other day. Yeah. So what I see and this is, again, when going back to the soggy middle, one of the things that I see happen, particularly to short story writers who are like, oh, and suddenly it's a novella. Is that they put too many barriers in. Yeah. So the difference is a barrier is something that is between you and the goal, like maybe a literal door. Sometimes it's a priest. The try-fail cycles are the things you do to try to get through that barrier. So if I've got a door, the smartest thing I can do is try the knob.
25:02Does it work? No. And I don't know where my keys are. Can I find my keys? Yes. But one of them breaks off in the lock. Am I able to, you know, like, do I grab a crowbar and just pry the door open? Yes. I'm through the door. And then I can do a, you know, yes, I'm through the door. Am I able to get to the barrier? And so am I able to get to my goal? And now I can do a big try-fail cycle, which is, am I able to get to my goal?
25:33No. And there are Bs. Well, and you can also play with an evolving understanding of what the barrier is. Yes. Right. You can start, I mean, I think about this as a GM a lot, where the players will be like, oh, the barrier is the door. And I'm like, no, the barrier is you don't know what's in that room. And you get into that room to find out. And so if you can't get through the door, you need to find another way in. And sometimes I see players get stuck there. And I, as a GM, realize, oh, I need to signal better what the actual barrier is. Yeah. Because everything I've done is say, this door is the barrier.
26:03So all they're thinking about is the door. Instead of communicating to them, no, your actual goal is that there are papers in that room that will lead you to the next step of this quest, which is to figure out who, you know, murdered the queen. I don't know. Yeah. But like, yeah. I think it really is focusing on the barrier over the goal. Exactly. Yeah. You're reminding me of shaggy dog stories that people tell in camp where the entire, if you Google this, if you've never experienced it, but like, it's literally like a joke in which it's like a series of locked doors.
26:33Each time you open the door, the next one's locked and you have to run back and get the key. And that's the one that we used to tell in camp. Why you didn't get all the keys at once doesn't make any sense because each time it's like another door. And the entire point of that is to frustrate the person who is being told the joke. Yes. And make them angry and then laugh at them, which is mean, but like, that's, you don't want your reader to have that feeling where it's like, you're just introducing door after door after door. And not only is it feel like it's too many barriers, but it also feels like the, the character's not getting any smarter.
27:05They're not bringing more keys. They didn't go buy a lock pick. Like after the 10th locked door in a row, they're not like, wow, this feels odd. Like, what should I be doing differently? Like if the try-fail cycle is exactly the same and the barriers are exactly the same, it feels like the character doesn't grow. Like you could have the same barrier and a new type of try-fail. You could have a try-fail and a new type of barrier. But I think the, both the same kind of feels very stagnant. Yeah. And something I just want to point out is that you can apply this to character growth
27:35also. Yes. And that, that is one of the things that the character can be like, oh, I should maybe try to change. I'm going to try something. And then like, I'm going to try standing under your window with a boom box. Yeah. Does that work? No, I look like a creeper. And now you've called the police. Like, you know. And I just want to point out also that try-fail cycles can be scaled to the type of story that you're telling, right? Like if you're writing a quiet story about working in a coffee shop, then your try-fail cycle is making the perfect latte, right?
28:07Or figuring out how to carry the milk you need without dropping it from the back room to the, to the front. You know what I mean? Like there are all these little things that you can do that scale to the size of the challenge that your characters are facing, but it still needs to feel connected to that character's growth, right? If their central question is, are they able to balance the 18 things that they need to be doing in their life, then put challenges in front of them and have them fail at multitasking and then figure out as they go, they're trying different strategies.
28:38When this gets boring is when you're asking your reader to go along with the exact same thing over and over again. It's like a video game fetch quest, right? It's like you, you went from point A to point B, you deliver it. And then like, okay, now bring this back to point A. And you're like, God damn it. I'm quitting this game right now because I don't want to walk all the way across this map again for no reason, right? Versus giving them a different kind of challenge to do that lets you see different parts of the map or explore the space in a different way or interact with things in a different way. I want to briefly, before we depart this episode, talk about how many try-fail cycles you should
29:12have because it's a question I get asked all the time. And the answer is that it is season to taste. But you should understand the effect of the try-fail cycles because the answer is, you know, it does depend on the kind of story you're telling. So we have previously talked about the rule of three, that people expect there to be basically three try-fail cycles. You know, you're going to, you know, three times is funny, third time is a charm, that
29:43kind of thing. So they're expecting this, you know, one, two, got it kind of beat or one, two, so anyway. The thing that you can do is you can manipulate that. So if you want something to feel really, really hard, then you give them four or five try-fails. And if you want it to feel easier, then you give them one or two. You can also look when you're manipulating the speed with which they accomplish something at whether you are giving them successes with a negative consequence or predominantly failures.
30:19So if you are like predominantly no's, if you are experiencing something where it just feels very slow, there's a chance that what's happening, even though there's a lot going on, there's a chance that what's happening is you're only giving the character no, and then this happens, and no, and then that happens, and no, and then that happens. It feels like they are never making progress towards the goal. On the other hand, if they are making progress towards the goal, but it feels very easy, even
30:53though things are going bad for them, you may be giving them a lot of yes, yes, yes. So you do have to sort of balance those two, and there's not an exact metric on which ones you use at any given moment. It's just an awareness that yes is generally related to momentum, no is generally related to backwards movement. And that can kind of give you some metrics with which to control how you're handling stuff
31:23in the middle. All right, so we have some homework for you. So for your homework, what we are going to do is think about some barriers. I'm going to ask you to look at the active mice quotient elements in your story, and I'm going to give you a little refresher. So milieu stories begin when a character enters a place, they end when they exit it, but all of the problems are about trying to leave.
31:55So in a milieu, you just keep them from leaving. Inquiry, somebody has a question, you keep them from getting the answer. Story is over when the character gets the answer. Character stories, they want to become a new person, you stop them, give them more angst. An event, they want to establish a new status quo, you stop them from doing that. So those are the goals. You're keeping your eye on that major goal, but you need some barriers between them and the goal. So what you're going to do is you're going to look at your mice quotients, make a list of barriers that go with each, and then from that list, you're going to select a smaller
32:31subset that play well together. So if you try to do every barrier that occurs to you, it will be too many. This is a way to have things feed from one thread to the other so your story isn't predictable and you're doing lots of new things. Don't worry, in the liner notes, if you visit writingexcuses.com, you will see a chart that shows you with a reminder of what their goal is and what your job is to do to your character as the author, what try-fail cycles to present them with.
Writing Excuses Conclusion
33:01So. This has been Writing Excuses. Writing Excuses. You're out of excuses. Now go try again.
33:09Writing Excuses has been brought to you by our listeners, patrons, and friends. Your hosts for this episode were Mary Robinette Kowal, Don Juan Song, and Aaron Roberts. This episode was engineered by Marshall Carr, Jr., mastered by Alex Jackson, and produced by Emma Reynolds. For more information, visit writingexcuses.com. If the world were like a Sleep Number mattress, everything would adapt for your comfort. Because as your life changes and your body changes, Sleep Number mattresses adapt and
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