Deadline Mindset

To state the obvious, writing deadlines often feel different than other deadlines. I almost wrote, ‘writing deadlines often feel different than real deadlines’. Which probably tells you everything you need to know about how well I manage my writing deadlines. Thinking about my schedule for this book and my repeated failures to stick to that schedule, I’ve been struck again by the amount of latitude we tend to give ourselves while negotiating deadlines within a large-scale writing project.

I currently plan to be finished my manuscript by March 2022 (a full year past my original deadline). While I’m now in a good position, this is largely due to undeserved good fortune: a generous extension to my manuscript deadline and a fortuitously timed sabbatical. I do know how fortunate I am. In my many fruitless attempts to get this project back on track over the course of the pandemic, I’ve had the opportunity to think deeply about deadlines. I have argued that nobody should push themselves to work normally during this time, but it hasn’t been easy to grant myself that leeway. I tried everything to create a workflow in which I kept up with writing while simultaneously finding the energy required for online teaching, handling an unusual amount of administrative work, and managing the rest of my life.

During my many attempts to right this ship, I tried to envision a range of possible options:

Scenario One: In this scenario, the writer meets their deadline, no matter what, and does so with a fabulous piece of writing. This best-case scenario is obviously the one that anyone would choose, except that it may be genuinely unattainable. I’m including it–at the very real risk of annoying you–because it is instructive to imagine what it would actually mean to meet a particular deadline. This is the would-if-I-could option.

Scenario Two: Here we recognize that a deadline may be truly impossible, leading to a decision to postpone completion. This decision allows work to continue with a desirable intensity but without the unrealistic pressure of the first scenario. This is the what-I-can-actually-manage option.

Scenario Three: This scenario is, to me, the novel one. Imagine that we could treat writing deadlines as firm, meaning that we would meet them and do so by compromising on what it meant to be finished. This approach is somewhat akin to the way many of us treat non-writing deadlines. When such a deadline is firm, we generally meet it and–since we can’t manufacture time–we tend to make the necessary adjustments to the quality of our work. We accept the notion that we might have done a better job with more time; however, when time ran out, we made the best of what we had. This is the stick-to-the-plan option.

The first scenario was, for me in 2021, never going to happen. I kept building schedules to support the impossible deadline, but always with the suspicion that they wouldn’t work. Why even build a schedule that I couldn’t meet? We’ve all been enjoined over and over again to set realistic goals. That realism would make sense if we had reliable knowledge of what is and is-not realistic. In practice, we often don’t know how long a writing task will take. More importantly, our orientation to writing is such that we will often take advantage of a lenient schedule. In my experience, creating a generous schedule doesn’t lead to finishing writing projects early. Given all this, I generally recommend continuing to set ourselves challenging writing deadlines.

The potential hazard of these sorts of stretch goals is, of course, that they will make us feel bad all the time. Nobody needs that. One way to avoid that regret is to recognize the true nature of overly ambitious goals: they are designed to create space for writing that might otherwise go undone. However, in order to get the benefit of setting ambitious goals without the psychic costs, we need a sound default plan.

In my experience–both as a writer and as a close observer of other writers–most people default to scenario two. When the ambitious schedule fails, we choose to slow down and do what we can actually manage. It’s appealing to take a breath and ensure that at least some of the job is done right. This scenario simultaneously promises us more time and more quality, two things all writers want. But it can easily lead to endlessly deferred deadlines.

If scenario one is unlikely to succeed and scenario two is a recipe for repeated deferrals, what else can we do? This is where scenario three comes in, as a different type of fallback position when the ambitious schedule crashes into reality. By ‘sticking to’ your plan by compromising on quality (for now), you may find yourself farther ahead. If you can’t have five outstanding chapters, how would you feel about five so-so chapters? Might that be a better basis for revision than one-and-a-half outstanding chapters? This strategy is the one that I tried this past year, with some success. I wanted a full draft by the end of 2021; as long as you squint just so when you look at it, that’s what I have. No, you can’t see it–it’s terrible! But I tried to proportion my efforts so that I kept moving, resulting in a full set of flawed chapters. In each case, the chapter was roughly all done rather than only partially done.

I made this decision because I wanted to experiment with this deadline mindset. I see two reasons to try to import the notion of firmer deadlines into our writing lives. First, we are notoriously bad at knowing when something is good enough to move to the next stage. Given the rampant perfectionism among academic writers, it might make sense to replace that evaluative metric with a time commitment. Second, we all stand to gain from treating self-imposed deadlines as a little stricter. Writing deadlines are often flexible in the sense that the actual moment when we miss one is private; however, they matter because a writing schedule represents a larger commitment to ourselves and our professional plans. Experimenting with firmer deadlines in our writing lives might lessen our common tendency to defer writing in ways that are deleterious to our own well-being.

I’ve been speaking in this post about the type of interim deadlines that have the power to keep a writing project on track. Using this deadline mindset for the ultimate deadline of a writing project would obviously be much more challenging: letting go is hard! But so many of our writing deadlines necessarily represent the interim stages of a writing project. Indeed, creating and meeting interim deadlines is crucial to getting to the final stages of a writing project. By creating more efficacy in our writing schedules along the way, we put ourselves in the best possible position to handle the undeniable stress of submitting a final draft. I look forward to having the chance to reflect more on that challenge in the coming months!

This post is the eighth in a series of book reflections posts. As I go through the writing process, I’m pausing to talk about my progress and my thoughts on the writing process itself. The progress reports are really just for me: I’m using the public nature of the blog to keep me accountable. The actual point of these posts is to reflect on what I’m learning about writing and how these insights connect to the topics covered here on the blog.

Status Update: As I said above, I’m in the home stretch. My work over the coming weeks will be a combination of tightening, supplementing, harmonizing, and jettisoning. Except for that last one, these activities are very satisfying. At times, it’s a bit confounding trying to use my own revision principles to revise what I’m saying about revision, but I hope my own struggles will ultimately make the book more humble and more helpful.

2 responses to “Deadline Mindset

  1. Thank you for this blog post. I very much identify with your descriptions of struggling with deadlines. I think the differentiation between the usefulness of a scenario-three approach to an interim-stage deadline and a final deadline (for a published piece of writing) is extremely helpful. Much of my writing anxiety is that feeling I have no control over whether I will meet my writing deadlines. It always takes longer than my best estimates, I never feel able to write faster no matter how much I want and need to, and I tend to only consider that final deadline a real deadline. Finding a way to reframe my relationship to self appointed, interim deadlines from a scenario-three approach, if I can manage it in a way that breathes immediacy into said deadlines, would probably help me in my quest to separate my ‘creator’ from my ‘editor’ when writing — again something I need and want to do, but haven’t really succeeded in doing.

    • Thanks, Laura. I think your point about a lack of control is really important. I hadn’t thought of it quite like that, but it’s a good way of characterizing our anxiety that we won’t meet our deadlines–because we can’t just MAKE writing happen. And we all write under the shadow of how we’ve managed (or mismanaged) writing in the past. That’s why I think it’s so valuable to be self-reflective and open to experimentation. All the best with your writing!

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