How to Manage a Difficult Book

Therese stepping in for a moment to introduce our newest regular contributor, multi-published author Rachel Toalson! You may remember Rachel from the interview our own Grace Wynter did with her several months back. (If you missed the interview, it’s worth your time — just click HERE.) Rachel’s generosity of spirit made it seem like she was a WU’er already, and happily for us she was interested in making it official. Welcome, Rachel!

Very few writers I know would consider a book easy to write. Most books require considerable commitment, time, and dedication—which, some days, translates to complete enthusiasm and love for the very best job in the world and some days translates to a slog akin to running a half-marathon in ninety percent humidity.

As writers, we come to expect these ups and downs, these easy days and difficult ones.

But what about when a book feels hard all the time?

Some projects give us more trouble than others. They feel hard to brainstorm, hard to write, hard to revise, hard to diagnose, hard to finish, hard at every stage of the process. Even if we have all the tools we need—an expert grasp of story structure, enough experience with character development to write a book on it, and an open mind ripe for collecting ideas—some projects are still harder than others.

What do we do when all our familiar tricks and skills don’t unlock a difficult book?

First we need to analyze the problem.

The first question I ask about a project giving me trouble is, “Why is this book so difficult to write?” I try to be honest about the answer. And what follows are the most common traps I’ve discovered in my own writing.

Sometimes a book feels difficult because we haven’t done enough work up front on the manuscript.

 I know there’s a debate between pantsers and plotters. I’m what I call a brainstormer. I brainstorm characters and plot and character journey and setting before I even write the first word—and yet sometimes I still run into a project that feels practically impossible to write. Usually this is because I’ve rushed the up-front work (because I just want to get started!) and I still don’t know enough about something in my story—whether it’s the main character, the supporting characters, the plot, the setting, the emotional wound, the character arc, the motivations that drive my characters, or even the tone or voice I want to use to write the story.

If a book feels difficult because you don’t know enough about it, go back to the beginning. Examine the character. Listen to them speak. Figure out what you’ve missed along the way and be open to pivoting.

Sometimes a book feels difficult because we’re putting too much pressure on ourselves.

Writers are great at this. We start a book, and we forget that we’re just writing that first draft for ourselves. Little thoughts start sneaking in—What will people think? Am I getting this right? Where will this be positioned in the market? What will my critique partners/agent/editor say about it?

Or maybe they’re not questions. Maybe they’re definitive statements like, This is terrible. This is the worst thing I’ve ever written. I am a horrible writer. I can’t believe I thought I could do this. I will never be able to sell this manuscript.

Take the pressure off. Get a first draft down. Let it be messy. Let it not make the least bit of sense in places. Let it be full of problems and inconsistencies. A book is never perfect on the first draft.

If you’re dealing with a second or third or fourteenth draft, you can still take the pressure off. Just repeat to yourself, “All I have to do is write the thing.” All you have to do is write the thing. What happens after that is not your concern right now—so don’t think about it. You only have to get words down on a page. Judgments come only after the writing is done.

And perfectionism? You’ll never finish a book if you expect it to be perfect in every way. I’m a perfectionist myself. And every time I turn in a manuscript to my editor, I release it by saying out loud, “Well, this is the best I could do today.” It’s a phrase that gives me hope—because if we’re doing our jobs correctly, we’ll be improving as writers every day. Every composition. So all we can do is turn in our best work today.

Sometimes a book feels difficult because we’re in the wrong headspace.

We may be tired or burned out or too close to the project. Or it might be that the book deals with difficult subject matter.

A recent project of mine was a very personal story. It dealt with some childhood trauma for which I’ve been in therapy for years. The project took me years and multiple drafts to finish—probably the most drafts I’ve ever done for a story. I thought I would never finish it. I wrote it first as prose, then turned it into a novel in verse, then turned it back into prose, then poetry, and on it went. Just finding the right structure for it felt impossible. It wasn’t until the eighth draft that I finally settled on journal entries that felt right for the voice, the character, and the story itself.

The story unlocked. That draft flew.

Which leads me to a few suggestions. If a story is feeling difficult for you to write, try one or several of the following:

1. Play. Play in every sense of the word. Play with story structure. Try a different format—turn your prose into poetry. Write a couple of chapters from another character’s perspective, as though they’re the main character. Change from past to present tense or vice versa. Try third person instead of first person. Play with bits and pieces of your book and see if anything you do makes it feel easier.

In the same way, try a different writing method. If you write in the morning, try writing in the afternoon. If you write only on the computer, pull out a notebook and write by hand. (I write all my first drafts by hand and all my subsequent drafts on the computer; there’s a magical connection between the brain and the hand, I think.)

If you write mostly at home, try writing at a coffee shop or in a park. Write using the voice memo on your phone while you’re driving somewhere. If you’re a plotter, try pantsing (I do this for one story out of every four or five, just to change things up); if you’re a pantser, try plotting. Play with prompts. There are plenty of resources out there to get your brain firing.

Just don’t be afraid to try something different. It may fail massively—but what if it doesn’t?

2. Take a break. If you’re feeling burned out or too close to the story or like you’re failing to make any progress on it, take a break. Put it away for a week or two or a month. Or for an hour while you go out for a long walk. Taking time in nature and moving our bodies can get the brain working on solutions even if we’re not actively considering specific problems.

Take a nap. Read something. Watch an episode—only one!—of your favorite show. Look for inspiration while staring out the window. Exercise. Do some yoga. Meditate. Write on another project. (I always have one or two projects going at a time so if I feel stuck on one I can just move to another.)

None of this is wasted time. The brain continues to work on our books even after we put them away.

3. Set a timer and take it in small pieces. This is a trick I use on myself when I just don’t feel like writing on a project. I set a timer for fifteen or twenty minutes and write as much as I can in that amount of time (even if that “writing” is just staring into space, thinking about my story). If I feel like things are going well, I’ll do another round of fifteen or twenty minutes, with a second timer. And on and on until I’ve reached an hour or until the time stops feeling productive, whichever comes first.

(If you’re wondering why only an hour, this is my best explanation: I find that if my brain is too fatigued on one project, I start sacrificing form—much like when my body is fatigued on mile ten of my morning run. Everything starts falling apart. Form flails, because I’m just trying to finish. I’ve found that’s true for my creativity, too—things no longer feel fresh on that project after about an hour.)

This trick also helps if a book in its entirety feels too overwhelming. Many times, when we start a book, we’re already looking toward the ending—which tends to add pressure and impatience to the equation. Even an easy-to-write book will feel much harder once pressure and impatience join the writing.

4. Connect with your people. We thrive on connection. We need human interaction. And sometimes our writing locks us away for hours at a time. Talking with the people in our lives—family members or friends or writing colleagues—can help clear our minds and refresh us.

In the same way, talking with writing friends about the problems you’re having with a difficult book can help generate solutions.

Every morning at 10, I meet with an amazing group of writers over zoom. At least once a week one of us brings an issue to the group—we need help with a title, or we need to know if the motivation of one of our characters makes sense or we simply need some encouragement to continue work on a difficult project.

It’s amazing the solutions you can come up with when you get a handful of creative minds together. Outside perspectives can give us new ideas and insights into our projects. Exchange manuscripts with another person. Ask questions. Share the burden.

Books can feel difficult to write for a number of reasons. But with an open mind, a playful spirt, and some relationship support, you’ll manage its complexities. And remember: oftentimes the hardest books to write are the ones that make the most difference in the world. So keep writing. The world needs your words!

Why do your projects sometimes feel difficult? Have you done enough work up front, or are you in the wrong headspace? What other reasons have you found a book might be difficult to write? What sorts of out-of-the-box tricks do you use to help you make progress on a difficult book? How do you engage in play when you’re writing?