How to Make It Through the Middles of Your Projects

Middles are tough.

It’s no accident that Dante began The Inferno, his allegorical journey through Hell, thusly:

Or that Christian, the pilgrim in John Bunyan’s allegory The Pilgrim’s Progress, encounters the bog called the “Slough of Despond” midway along his journey.

Midway upon the journey of our life
I found myself within a forest dark,
For the straightforward pathway had been lost.

At Grub Street Writers, where I teach, many writers refer to the “Murky Middles” of writing projects.

Dark forests, bogs, murk: you might get the idea that a lot of people find middles not just difficult, but confusing and downright scary.

Dante Lost in the Woods
Dante Lost in the Woods

Here’s the problem with middles:

  • The piece (or project) is no longer fresh and new and shiny. Your early energy and enthusiasm are waning.
  • At the same time, the piece is at maximum entropy: meaning, what you’ve done up till now is super chaotic and disorganized.
  • You’ve also become more aware of the piece’s problems. It’s not living up to the pristine, Platonic vision that initially inspired you!
  • Moreover, you’re not even sure how to solve the problems, or whether you’ll even be able to solve them.
  • And the end is nowhere in sight.

The middle, in other words, is where the work gets tougher at the very same moment that your enthusiasm weakens.

No wonder you’re discouraged!

It’s also easy to see how the whole thing could snowball into an avalanche of disappointment and discouragement! (Forests, bogs, avalanches—it’s all getting worse and worse!) This is particularly likely if you perfectionistically constantly judge your output: e.g., “This word sucks. That sentence is so inelegant. This project is badly organized. I’ve mismanaged the whole thing. It’s doomed to failure. No one’s interested, etc.”)

Here are some tips for getting through:

1) If you’re struggling in the midst of a project, recognize that you might not, in fact, be doing anything wrong. It’s just the Murky Middle!

2) Maintain your perspective—this won’t last forever, and like Dante, Christian, and many other intrepid voyagers, you, too, will eventually reach paradise. (Or, at least the end of the work!)

3) Be extra vigilant about perfectionism, and extra diligent about using your tools, including self-compassion and timed writing intervals.

Of course, this entire discussion applies far beyond writing. Dante and Bunyan were writing about one’s spiritual development, and relationships also can have Murky Middles. (I was warned about it in foster parent training.) The Murky Middle also happens during hikes and quilting projects and probably all of life’s important or challenging endeavors.

Middles are Massive

Anne Lamott famously said, in her creativity guide Bird by Bird, that every piece of writing begins with a “shitty first draft,” but it's probably more like ten, twenty, or thirty shitty drafts. Make sure you understand what a “draft” is, though: a single, quick run-through of your piece (or chapter or other section), during which you correct its obvious and easy problems, and partially correct its hard ones.

You move quickly and lightly through the piece, making incremental improvements and resisting the temptation to drill down or bog down on any one problem.

Then, when you get to the end, you repeat the process over and over again; always moving fast and keeping a light touch. Through these repetitions, you gradually gain insight into your piece's true meaning and form, and solve nearly all its problems, including the tough ones. (Always ask a colleague or mentor for help with the hard ones—don't get stuck.)

Many drafts = a "massive middle." But don't despair! You actually want a massive middle because...

Quality Happens "Automagically" in the Middle

Continue the above process and, at some point, the piece will “magically” (that's really how it feels!) attain “non-shittiness,” meaning it will have become well-organized and coherent. At that point, the writing process becomes mostly easy and fun copy-editing and other polishing.

So, let's assume that the first 15% of most pieces is the inspired part, and the last 15% is easy copy-editing. That leaves a giant middle of 70% where you're thrashing around in the thickets.

Only, be sure not to thrash! Maintaining a light, fast touch is the best way to ensure that you not only get the piece or project done, but have fun doing it.

One more thing to remember...

Middles Have Middles!

Yes, you can have a middle-of-a-middle. Here's how it works:

Many endeavors begin with a “honeymoon period” where the work is fresh and new, the possibilities seem endless, and you're filled with energy and enthusiasm. That's the beginning of the project.

Alas, like all honeymoons, it too soon comes to an end. Reality sets in, and inevitably disappoints. The work doesn't come together as easily as you had at first imagined, and you become aware that what you write may never live up to your pristine early vision.

Your motivation wanes, but you resolve to soldier on.

And then, you hit a point where everything seems particularly bleak. I call that the “anti-honeymoon,” and the most famous fictional example is probably the “Slough of Despond” (or, in modern parlance, “Swamp of Despair”) from John Bunyan's The Pilgrim's Progress:

'This miry Slough is such a place as cannot be mended; it is the descent whither the scum and filth that attends conviction for sin doth continually run, and therefore is it called the Slough of Despond: for still as the sinner is awakened about his lost condition, there ariseth in his soul many fears, and doubts, and discouraging apprehensions, which all of them get together, and settle in this place; and this is the reason of the badness of this ground.

For many projects, the anti-honeymoon occurs about 25% of the way through.

 The Slough of Despond
The Slough of Despond

The Slough = Perfectionism

In The Pilgrim's Progress, the Slough consists mainly of the pilgrim Christian's “fears, and doubts, and discouraging apprehensions.” In other words, it has less to do with his actual predicament, and more to do with his perceptions of, and reactions to, that predicament. (See also: perfectionism.)

The important thing to remember about the anti-honeymoon is that it's temporary: just keep working and eventually things will improve:

You'll return to the "normal middle" of the piece where things aren't so bad, and then eventually make it to what Christian would have called your "Celestial City," where:

(a) The end of the work will be in sight, and the work itself will get easier. (You'll be focusing on details instead of making major changes and corrections.)

(b) Although the result probably won't be exactly the same as you initially envisioned, it will probably be fine, and you will be proud to have accomplished it.


Good luck using these techniques. As always, I welcome your questions and feedback.

  Dante Arrives in Heaven
Dante Arrives in Heaven

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