To the Wire

Get Your Writing (Or Anything Else) Done on a Deadline

“Where’s the boy, String?”
—D’Angelo Barksdale

Today’s Shelf Life is not about The Wire, so please take a moment to adjust your expectations. I apologize if the title is misleading. If you have not seen The Wire, you should see it. There! I have satisfied my white-personly duty of advising other white people to watch The Wire. It’s a thing we all do, like telling people about the fair-trade coffee we drank the other day or admiring our friends’ mid-century modern furniture. This phenomenon is universal as far as I can tell. I once dated a Londoner who, trying to impress me, said he actually knew a thing or two about the Baltimore area having seen The Wire, and had I seen it? I have never offended someone so much in my entire life as when I replied, “Man, white people sure love telling other white people to watch The Wire.”

Today’s Shelf Life is about setting and then achieving deadlines and will not touch on the obvious merits of the Hilti DX 460-MX.

Having now spent most of my career (thus far) in publishing, deadlines are my jam. I actually can’t do anything without a deadline, work-related or nah, which makes my partner crazy. I suspect all kinds of work have deadlines but it seems that whenever I interface with someone outside of publishing they don’t really understand how deadlines work or why they are important. Or, I suppose, deadlines just work differently in other fields—vague, plastic, changeable. I immediately go into suspicious mode when someone asks me to do something “ASAP” because “ASAP” is not a deadline and in the publishing world it means, “I want you to deprioritize everything else in favor of what I have just asked for, but when there’s a reckoning due for why everything else was deprioritized I won’t take any responsibility.”

I’m sharing my thoughts on the definition of “ASAP” because that concept figures heavily in my writing life. If I’m doing something “ASAP” that means I am doing it right now or I am doing it never. There is no in between. That’s often when my writing happens—right now or never—which I know is true for many others as well. That’s because we’ve given ourselves a deadline of “ASAP” and that is not a deadline.

A deadline is the last possible moment to get something done before it’s too late. In school missing a deadline might mean you can no longer turn in your assignment and receive credit for it. In many jobs missing a deadline means you will be in trouble with your supervisor, and maybe a project or product will be delayed. In life generally, I find that if I don’t associate a deadline with something then it’s just a thing I might do sometime in the hazy future. Until I give myself a timeframe, nothing is actionable. 

If you find writing is like that for you—right now or else at some unspecified theoretical future date and never anything in between—then you might need to assign a deadline to instill the motivation you need to get and keep moving.

The term deadline originated as a spatial rather than temporal limitation. A deadline was the line painted around a prison that indicated how far a prisoner could go before being shot. Later, it was adapted for the publication world to mean a line on a printing plate outside of which text would not print. Later this concept was adapted metaphorically to mean the time beyond which something could no longer be done—the latest time something could be completed and be valid. The word deadline, though, still retains its original association with death. It feels ominous in itself, without even the looming pressure to complete an objective or task. It gives many people that familiar feeling of dread in their gut, like the feeling you get when you want to know where Michael B. Jordan is but Idris Elba won’t say.

If you’re trying to get writing and keep writing till you finish something, try these four steps to put the magic of deadlines to work for your project.

Figure Out Your Deliverable

This is defining your success criterion (or criteria) all over again. Before you can set your deadline, you have to know what it is that must be completed by that deadline—your deliverable.

You may have just one deliverable or you may have many, and each piece may be big or small. It doesn’t matter. Start by making a list of what it is you want to write: A poem? A chapbook of poems? A short story, or a collection of them? A novel? A trilogy? The sky’s the limit at this first stage. Try to get your mind around the whole of what it is you want to write, however big or small that is. We’re going to break it down into manageable chunks in a second.

Once you have your mind around the entire project, figure out how much writing that project really entails. How much work are we talking about when we say “a novel” or “a trilogy of novels” or “a collection of six intertwined short stories”? Before we can break the work down into meaningful units, we need to assess how much work it is.

It’s important to bear in mind that there’s no right and wrong quantity of writing. I am in favor of telling the story you have until it’s done and then figuring out later what you have on your hands—A short story? A novella? A novel? A duology? There’s no correct number of stories to have in a collection, there’s no wrong number of words for a novel. 

That said, if you have a goal of selling your writing to an agent or publisher, there are standard word counts to target to make that a more realistic possibility. The information is out there for you to search but generally speaking, you will have a hard time selling a novel under 40,000 words or over 120,000 words—and those are extremes tied to specific genres. A good target for most types of fiction and creative nonfiction is 50,000 to 80,000 words. Short stories are saleable over a wide range of lengths depending on the outlet you want to sell to (or the contest you’re submitting to). Flash fiction can be anything up to 500 words, while full-length short stories can go to 10,000.

If you know you want to write a trilogy of novels, you could have 150,000 to 300,000 words ahead. If you want to write a short story to submit to a contest, maybe you’re looking at 7,500 words. Either way, you’ve figured out the scope of the whole project.

The final piece of this step is to figure out the deliverable you’re going to focus on first. For this purpose, we want a discrete piece of content—something you can finish and enjoy a sense of completion, even if there is ultimately more to write. Don’t make this deliverable too small and granular (a chapter or a scene) but don’t make it too grand either (an entire connected universe of novels). A complete short story, novella, memoir, or novel would be an excellent deliverable to plan for.

Set Your Deadline

Now you’ve got your deliverable in mind and you know about how much writing (or work) it’s going to take to get it done. The next step is to set a reasonable and meaningful deadline.

By reasonable, I mean a deadline that has enough time for you to accomplish your task without giving you so much time that you can procrastinate on getting started (a sure recipe for starting never). Figure out what a comfortable writing pace is for you, both in terms of how quickly you write when you sit down to do it and how often you can sit down to write and for how long. If, when you write, you usually turn out 500 words an hour, then you’ll probably need 100 to 200 hours to crank out the volume of words needed for a novel—if all you have to do is draft. Don’t forget to factor in pre-writing work like research and outlining. Let’s say you think you need about 200 hours to write your novel and you know you can devote two hours a day three times a week—then you’d need about 34 weeks of time.

Once you know how much time you reasonably need to write your piece, choose a meaningful deadline. When I say a deadline should be meaningful, I mean you shouldn’t just pick it out of the air. For instance, if you have decided the task you have ahead of you will take 34 weeks, don’t look 34 weeks out on your calendar and choose that date. If you choose a date arbitrarily, a part of your mind will always know that you can move that date without any consequences.

I have greater success with deadlines when I connect them to a date that is meaningful to me in any way—it could be meaningful in a way that is unrelated to the task (eg, “I want to finish before my milestone birthday this year”); it could be meaningful in a way that is directly related to the task (eg, “I’ll finish in time to pitch during the January 2022 #PitMad event”); or it could be meaningful in a way that is tangentially related to the task (eg, “I need to finish before my classes start in September, because then I won’t have as much time for writing”).

Choose your deadline so it reasonably allows you enough time to be successful and so the date is tied to a meaningful event or day in your mind. Once you have the magic date chosen, move on to milestones.

Choose Your Milestones

Milestones break your project down into phases so you can check, as you progress toward your goal, how you’re tracking against your ultimate deadline. When you achieve a milestone on schedule you know you’re on track. When you miss one, you’re off track and will miss your deadline if you do not change something. That’s your cue to look at where you can make an adjustment in the project plan to get back on track.

The project manager you know will want you to break the writing down into your planning phase (research, character development, outlining); your drafting phrase (writing); and your revision phase. If the deliverable that you want to come up with by your deadline is a submittable piece of writing then this is a great plan. Those are three distinct phases with several different actionable tasks in each phase that will allow you to break the plan down to a very manageable level of granularity. Your milestones in that case would likely be (1) the completion of a finished outline; (2) the completion of a finished first draft; and (3) the completion of a finished final draft.

But if you just want to crank out a finished draft and you don’t want to include the planning and/or revision stage in your project, then you’ll need to come up with different milestones. Think about where your project logically breaks into parts that are reasonably similar in magnitude. Chapters are a possibility, but depending on how many you have you’ll probably be looking at an unwieldy number of milestones. For a novel, parts or acts would be better milestones than chapters. For a short story, you could break your work down into (1) the exposition; (2) the action; and (3) the climax and resolution—all things that most short stories will have.

You don’t want too many milestones because they need to be pegged to dates and you don’t want to be tracking every small accomplishment with that level of specificity—that’s a quick way to get discouraged. Pick three to five major milestones and set interim deadlines on your calendar to peg them to. You don’t need to live and die by them like you do your final deadline, but keep an eye on them to make sure you stay on the right course.

Break Down Your Plan

My favorite part of project planning is breaking my plan down into the tasks that I need to complete to meet each of the milestones I picked out. Depending on how you broke your project down into milestones in the previous step, the units of work you’re going to come with during this step will look different. If every milestone is a piece of your draft, then your work units will be fairly similar and uniform. If you have planning, drafting, and revision stages to take into account, then you’ll have a wider variety of tasks. Either way, during this step you are breaking your writing project down to tasks at the smallest level of granularity that makes sense. 

If your deliverable is an unrevised draft and your milestones are the three acts (or multiple parts) of your story, then you can further break each act or part down into its component chapters and, still further, each chapter down into the scenes it contains. Once you’re down to the scene level you can’t meaningfully break the writing apart further—a scene is the smallest unit of storytelling. It doesn’t make sense to group parts of a story by the paragraph, sentence, or word. 

If your deliverable is a polished, submittable draft of something and your milestones are planning, drafting, and revising, then you’ll have different tasks. You might break the planning phase down to ideation, character development, outlining, and worldbuilding—or any other set of planning tasks that make sense to you. Your drafting phase may be broken down to chapters and then scenes as above. And your revision phase might be broken into alpha/beta/gold, or first/second/third revisions—whatever makes sense to you. 

Keep breaking down the tasks that you come up with until you can’t break them down into anything smaller that still makes sense as a distinct task or unit of work. I think this is like factoring in math, where you continually break down numbers into smaller numbers until everything is a prime that can’t be divided further. Don’t quote me on that, I don’t know how to math.

Once you’ve got your project fully broken down, you can identify whether any of your tasks have dependencies on other tasks—whether any task can’t be started or completed until an earlier task has been started or completed. You don’t need to do everything in an order that makes chronological sense. You don’t have to write chapter 1 before you write chapter 20. But you do have to finish your draft (of any unit of text) before you can begin revising (that same unit of text). So make sure you have any critical dependencies in mind when you’re deciding in what order you want to tackle your pile of now-very-manageable tasks.

For the project managers among us, today’s article probably felt like an extremely barebones and superficial explanation of planning a project. It’s meant to be. If project planning is not something you have experience with, I hope this guidance is helpful for you in visualizing your amorphous writing project as an actionable set of tasks to accomplish to have a finished story or manuscript in your hand by your carefully chosen deadline. You can figure out your deliverable and set your deadline right now—you can probably do it in less than half an hour. Those two things are all you need to turn your “maybe I’ll do it someday” idea into a goal that you’re actively working toward.

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