Fifteen minutes long, because you're in a hurry, and we're not that smart.

15.37: Writing Under Deadlines

Your Hosts: Brandon, Victoria, Dan, and Howard

What’s it like to write under a deadline which has been set for your project by someone else? What strategies might help you bring the writing in under the deadline?  Can you train yourself to be ready for this?

Those are all good questions. Hopefully we won’t run out of time to come up with answers…

Credits: This episode was recorded by Dan Thompson, and mastered by Alex Jackson.

Homework: Experiment with a “stay on target” time management tool, like the Forest focus app, or something similar.

Thing of the week: Overly Sarcastic Productions (YouTube channel).

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As transcribed by Mike Barker

Key Points: Writing to contracted deadlines is hard. Sophomore slump! Writing in a bubble. It gets worse! New level, new devil. Train yourself to write against deadlines. Train your good habits. Build sustainability. Watch out for the year and a half deadline — you need to work consistently at the start, to avoid crunch time at the end. Remember you won’t have a boss. Pay attention to your own nuances. Make time to have a flat tire. Watch out for the other cooks in the kitchen! As your career grows, more things take time away. Learn to juggle early! Build a trunk full of pieces to use. Being good at deadlines, able to juggle multiple projects, means you will always have work. Learn to make your own schedule. 

[Mary Robinette] Season 15, Episode 37.

[Brandon] This is Writing Excuses, Writing under Deadlines.

[Victoria] 15 minutes long.

[Dan] Because you’re in a hurry.

[Howard] And we’re in a hurry, too.

[Brandon] I’m Brandon.

[Victoria] I’m Victoria.

[Dan] I’m Dan.

[Howard] I’ve gotta go. I’ve got writing to do.


[Brandon] I’m not sure if we ever even talked about this before. Maybe briefly. But I don’t think we’ve ever had an entire episode on writing to deadline. Which is something we should totally do, because, I don’t know about the rest of you, but the first time I had a contract, I was surprised by how much harder it was to write under someone else’s deadline than my own goals.

[Victoria] Yes. I think this is called the sophomore slump for a reason. The first book you write usually is not under contract. If you’re lucky enough to get a contract, and the contract extends for more than that book, the next book you write will be the first book that you write under contract. I say that it’s like going from riding in a cave to going into writing in a bubble. Where all of a sudden, everyone can see you, and everyone has a stake in it, and everyone’s watching you, and you no longer have unlimited time, you have give or take six months. It is one of the most trial-by-fire processes. It’s one of the reasons that second book hits so many people so hard. Because second book… All books are difficult, but the first book you write under contract is an eye-opener.

[Brandon] For me, I had two big distinct moments like this. The first was writing my first book under deadline. The second was when I had The Wheel of Time. Suddenly, a lot more eyes were on me. I’m glad I was able to step into that. That I… My early books were not as… I was a brand-new author. They did fine, but it was when I suddenly had everyone at the company, at the publisher, focused all of their attention on me, that suddenly writing under that deadline was a very different experience.

[Victoria] Well, that’s the horrifying thing, right? If any of you out there are writing your first book under deadline, it’s only going to get so much worse…


[Victoria] Because you’re still a new author. That first book you write under deadline feels like… Much like when you’re a teenager and everything feels like a 10 or like the end of the world. That first book you write under deadline, you feel like it’s never going to be this hard again. Until something else… My agent would say, “New level, new devil.” The idea that every time you step up a level or into a new spot, you have that same sophomore horror reaction again at a new hurdle.

[Brandon] I think a lot of our listeners will, again… I say this a lot… Will be thinking, “Wow…”

[Howard] Luxury!

[Brandon] I know, wouldn’t it be so nice?

[Dan] Wish I had that problem.

[Brandon] but I do think training yourself to write under deadline can be very helpful for preparing for a career in writing.

[Victoria] Absolutely

[Brandon] I’ve had many friends as writers hit this in it be really hard for them. A lot of times you’ll find someone whose first book comes out and then there’s a long gap to their second book. I’m not even talking about the famous examples that you might point to. A lot of my writer friends, one book came out, and then it’s like four or five years til their next book. That’s a really bad time to be making a big gap between books. Really bad time.

[Dan] So, when… Brandon and I were in writing groups together forever until he finally got published, and he got published a year, year and a half, two years before I did. So I watched this happen to you. I thought, “Okay, well, this is what I need to be ready for.” Because as soon as you had a contract, then your time was not your own, and you were under all these other pressures. So I was trying to teach myself how to write. So I started setting my own deadlines. Because I knew this was coming. So that was, I guess, the first step, if we’re going to give people advice. Give yourself an artificial deadline that you know is going to push you, that you know is going to be much harder than you want to deal with, and see what you can do with it.

[Brandon] This is part of why we like Nanowrimo and why… I did it years before I broke in. It was really helpful. For doing that first time I actually had a deadline to have practiced having deadlines.

[Howard] In the world of web cartooning, I made my entire career out of this deadline thing. Because I went 20 years without missing a daily update. There’s this rolling deadline which says there will be a comic strip up every day. As we are recording this episode, that deadline, the inked buffer is only seven days out. Which is a terrible place for me to be, but I know, after 19 years of practice, I know exactly how long it takes to get out of this hole. Do I know exactly what I am going to write for the two weeks of scripts that I want to write and pencil and ink next week? No. But I’ve done this enough times that I am confident that if I focus myself on Monday and I look at my outline and I fall back on craft… Mary Robinette has talked about this a little bit, there are times when we just fall back on craft. It’s not about inspiration, it’s not about the Muses, it’s chopping wood and carrying water. I know that I can do that. I just have to knuckle down and make it happen.

[Victoria] Part of this is a matter of training yourself into good habits. Because, as I said, it’s only going to get harder. The better habits you can devise, the better habits that you can really start… Not perfecting, but creating for yourself early on, are really going to come in handy if you move farther into a career and you have multiple deadlines or multiple publishers or multiple anything. Really, like, they also come in handy if at any point you move from writing as hobby to writing part time or writing full-time. Every one of these habits about enforcing your own deadlines, finding accountabili-buddies, like finding a generational buddy, like finding anybody that you can really look to as support system and people to keep you accountable, these are key things for more sustainability of deadline.

[Dan] You have to decide at what point you want to add this. Because if you don’t know how yet to write a book at all, you don’t necessarily need to step up to this hard mode. Play easy mode first, because that’s what it’s for. But if you look at your own career, your own writing that you have done thus far, and you think that you are ready to add a new skill on top of it. Even if you maybe haven’t even finished a first book, this is something to start building early.

[Brandon] The difficulty with being a writer… I mean, you may be sitting there thinking, I’ve dealt with deadlines, I’ve had schoolwork. We all have. This is a familiar thing to all of us. That’s good. You have some practice. But there is something very dangerous about having a year and a half to do something, that if you don’t do it consistently every week for the first eight months of that, your life is going to fall apart trying to do it for the last whatever, eight months of that. So, learning to be able to when it’s not a pressure, keep to your deadline, that’s a key skill. The other thing you’ve got to remember is you won’t have a boss telling you to. Even if you have an editor, most of the time, your editor’s not checking in that often. There assuming the book is working fine. They will go four or five months for checking in, and seeing how things are going, sometimes, if they’re busy with other projects. If you have let yourself spend these five months being like, “Oh, I can get to it,” or “I’m feeling really stressed right now, I’ll play Xbox,” and then… You’re just setting yourself up to crash.

[Dan] My grandmother grew up on a ranch. She had all these awesome aphorisms. One thing that she always told us as kids was, “If you don’t have time to do it right, you definitely don’t have time to do it twice.” Which is a principle that I apply to this. That it is about not just setting a deadline, but making a plan that is going to work now. So that you are using your time well now while it’s not crunch time, because you don’t want to get to crunch time, you want to avoid that as much as possible.

[Victoria] Also, especially early on in your deadline-written career, when you don’t quite know all of your own nuances yet… All of your own… Like, I know that the first third of a book takes me roughly three times the amount of time to write that the last two thirds do. I cannot allot the same amount of time for every act in my book. So… You really only learn these things, because whatever works is what works for you, you only learn these things by doing. You need to make sure that you don’t lean into procrastination techniques early on, or else you might find out the hard way that you don’t work like that.

[Howard] Back in May, we talked about mental wellness. Just how to take care of yourself, and how sometimes you need to take days off. I mentioned the Munchkin deck project that I was involved in, and how incredibly educational that was. Crunch mode is definitely a thing that many of us, a lot of us, can do. But it’s not something that you can maintain. It’s never something that you should build into the project plan. The… When I have… It happens all the time. People will say, “I can’t believe, how did you do this without missing a day? How is that…” Well, you do it, not missing a day, by having a huge buffer. My dad used to say, “You don’t leave for the airport unless you’ve got enough time to change a flat tire.” Which is not something I’ve ever had to do on my way to the airport, but that was just the way he built the plan. You have time to change a flat tire. I have time in my buffer, except this week, to get sick. To have the sewer line rupture. To have whatever.

[Victoria] Well, there’s something else that I do want to bring up, which is once those deadlines become contractually inputted instead of personally inputted… The reason that it’s so important that you stay on top of your side is because you’re not the only cook in this kitchen. You can hit every one of your deadlines, but if you’re the only person that you’re planning on, something at another point in the pipeline can go wrong. An editor becomes late, a publisher becomes late, and all of a sudden, your very carefully orchestrated machine falls apart.

[Dan] And once you have multiple projects going, and you’ve made your perfect plan and you think this book is working great, then the other project that you’ve already handed off to the editor, they throw it back and say, “Hey, sorry this took me an extra month. I need you to turn around these edits by the end of the week.” You’re like, “But… That ruins everything!”

[Brandon] Well, I mean, this even happens with… This year it happened to me with, I got beta reads back on a book and there were some responses to the book that I was not expecting. Where I’m like, “Oh. I need to do another revision. I can see now why these are happening. But it means I need to take an extra month on this book.” Although I was going to say, when Victoria was talking about editors being late, Dan and I know nothing about that.


[Brandon] Oh, no.

[Brandon] Let’s do our book of the week, which is actually a YouTube channel that I really like. This isn’t to give you excuses to not write. But, Overly Sarcastic Productions is a delightful YouTube channel where they do summaries of history, summaries of mythology, or look at various writing and storytelling tropes, and present them in a funny way. Just explaining to you what they were, give you the Cliff Notes version of the history of Herodotus or the Cliff Notes version of what it is, the amnesia plot, and how it’s used in various books. They are funny writers, they are funny deliverers. The woman who runs… Who is part of it does sketches for all these things and her art is a lot of fun. I just highly recommend it as 15 minute, 10 minute beats that you’ll probably like because you like this podcast, that are focusing more on tools that can help you be a better storyteller. So, give them a look, Overly Sarcastic Productions.

[Brandon] Now, coming back around on this idea of deadlines. One thing that I wanted to bring up is it actually gets harder and harder the better your career goes. This is not something I was prepared for. You usually do get, when you first go full-time, a nice breathing room dump. Where you’re like, “Oh. I have extra time. I have more time than I thought, than I ever had for my writing before.” That’s the most time you’ll ever have. That year while you’re writing before your first book comes out. My experience has been that once a book is sold, agents tend to be really good at getting you another project if you want one. It’s generally a good idea to get a second project and be working on that. Once the book comes out, suddenly there’s publicity to do and promotion. The more popular you become, the more successful you become, the more this takes a bite out of your time. To the point that I have less time to write now than I did when I was full-time working a job. Now, granted, I had a weird job where I could write at work. But I have less time than I did then. You would think, “Oh, Brandon, you’re full-time as a writer. You would obviously have more time now.”

[Dan] Just to give our listeners an idea, arranging this recording session with both Brandon and Victoria took us almost a year of planning.


[Dan] To find the right holes in the schedules. Because they’re so busy.

[Victoria] I will say I’m definitely one of those that… I’m very grateful for how my career is going right now, but between… I have four publishers and I’ve been in 16 countries so far this year. If you don’t think that takes a bite out of writing… And I know, I can hear people saying, like, “Oh, but you’re so lucky.” I am, but if I don’t also find time to write more books, that luck is going to run out very quickly when I run out of products.

[Brandon] This is a good time in your lives, before you’re published, to practice being able to juggle all of these things and know that you can work to a deadline even if other things are interfering. I wish I’d practiced it a little more during my unpublished days.

[Howard] It’s… Boy. It may seem hard as a new writer to take the novel you’ve been working on and that you’ve revised and to say it’s really just not ready yet and put it in the trunk. But… Boy, I gotta tell you, late career, having a trunk full of things that you know exactly how you put them together and you know exactly how to fix them and you’ve got a pretty good idea of how quickly that would go. That means that when an opportunity comes up where, hey, maybe I could file all the serial numbers off of this and turn it into some money, you can do exactly that.

[Victoria] Related to that, as well, I just want to say, do not undervalue the time between when you sell your first book and when that book hits shelves. That is the most beautiful time you will ever have. It is the clearest, free-est mental time you will ever have or reviews start coming in and before your monologue becomes a dialogue when it comes to your creative energy. But, like, cache anything you can, ideas, balance, learn good work life balance. Also, my favorite productive… Like, procrastinatory technique is the idea that social media is absolutely part of my job. I can do a whole lot of not writing being on social media and justify it as marketing. Really start to analyze, figure out what your best times of day for writing are, figure out when you can do this, figure out what’s going to be anything sustainable. Because it’s only going to get more complicated as you go down that path. So any… I know I’ve already said good habits, but any good habits that you can build early will serve you later.

[Brandon] If you can become one of the people that is really good at deadlines, that is worth gold in the industry. Because so many writers are… I won’t say bad at this…

[Victoria] I’ll say bad at it.

[Brandon] I would say…


[Brandon] There are a lot of professional writers that the best they can do is keep up to date on the one thing they’re working on, and that’s a struggle. People who can juggle multiple things become very in demand. Even if you’re not ending up as a bestseller, if you are a mid lister, but you are someone who can deliver something on time, there’ll be work waiting for you at every corner. You’ll never go hungry if you can turn in things on a deadline that is good quality work.

[Howard] My friend Jake Black has said on several occasions, be… You can be on time every time. You can be the absolute best in the industry. You can be awesome and fun and enjoyable to work with. If you can only pick two, you’ll probably find work. Pick easy to work with and always on time, because being the absolute best at everything in the industry… Boy, that one’s hard. The other two are so easy.

[Dan] Well, I wanted to say, that this is extra valuable, especially if you are mid list or even low list. Because you’re going to need multiple revenue streams to pay the bills and feed your children. My kids want to eat every day. I don’t know…


[Dan] Where they get off. But you have to have so many different projects and so many different irons in so many different fires that being able to come up with a good schedule is really valuable. I literally will take a print calendar, old caveman style, and I will mark on it every time that I can’t write. Then I will start reverse engineering. Well, I’ve got this project that needs to be done by this day. Build into that how much do I think I can write in a day. How much… Give myself some extra days when I know I screw up, so that I am not immediately behind on the treadmill. Give myself some self-care time. Then, see how much I can compress that. That’s how I do it.

[Brandon] Let’s go to our homework, which hopefully will help you with this.

[Victoria] So. This homework theme of the day is, writing friends, not surprisingly, trying to get you to put some structure into that free-form of writing. I use a very particular app called the Forest app, it leans into the Pomadera method, essentially a timed writing sprint. The thing I like about the Forest app, it’s only a couple of dollars. It is gamifying the entire process. You essentially pick a tree. You earn different kinds of trees to go in your forest. You grow different kinds of trees or certain amounts of time, while the Forest app is going. You cannot touch your phone and exit the app, or else the tree will die. The tree dies, and at the end of the day, you have a sad little dead defecated tree in your forest. The only thing I think could make it better would be if it were kittens or puppies instead. But, in the meantime, the Forest app is a nice way to keep track of writing sprints and find a way to just add a little bit of structure.

[Dan] You heard it here first, Victoria wishes she could kill kittens and puppies.

[Victoria] No one wants… I would never kill kittens and puppies.


[Victoria] I would never miss a writing sprint.

[Brandon] This has been Writing Excuses. You’re out of excuses, now go write.