The other day I asked a client how his memoir was going, and he told me he was thinking of quitting.

“It’s getting boring, reliving the same events over and over,” he said. “I’ve already told the story a hundred times; it’s not new anymore.”

This struck me because I often talk about writing as a process of discovery. I’m constantly learning from writing, and I forget that this happens sometimes: it can get stale. Sometimes we repeat ourselves. It’s like that friend who just went through a breakup and can’t stop rehashing it.

I wasn’t sure how to respond. I didn’t have a ready answer for how to reclaim a sense of discovery in writing. So I said, “Well, that’s understandable. Maybe it’s time to put it down for a while.”

But a few minutes later, now on a new topic, he said, “Well, there’s a part you haven’t read yet, because I don’t know how to write it.”

“What part is that?” I said.

“It’s something I’m wrestling with: how do I interpret so-and-so’s behavior? Do I give him the benefit of the doubt? Even if I don’t believe him? I don’t know where I land on it yet. It’s messy.”

“PLEASE,” I said, maybe too emphatically. “Wrestle with it on paper. Write about all its messiness and uncertainty. That’s exactly where the discovery can come in.”

If we only ever write what we know, if we never explore new territory on the page, if we believe we have to know exactly what we’re going to say before we start—then we deny ourselves the opportunity to stumble upon some new and deeper truth.

When we take a leap and start writing without knowing the end, that’s when we get to participate in the transformative process that is writing.

And that’s probably when the writing will get good, too.

Yet many writers I’ve worked with and students I’ve taught believe they need to know what they’re going to say before they start. This happens in nonfiction, fiction, school papers–all of it. And it tends to result in

1) writer’s block
2) loss of interest, and
3) flat, voiceless writing. The kind that’s as boring to read as it was to write.

I read this somewhere: “No surprise for the writer, no surprise for the reader.”

Right. When the writer is just rehashing, the reader will likely sense that. It will lack a certain glimmer and urgency and “realness.”

On the flip side, readers can also sense it when the writer is exploring. There’s honesty in that, and freshness, and those are two characteristics of good writing that you just can’t fake.

I think this is why people are so enamored by morning pages: it leads them straight into the weeds and encourages them to stay there. It’s counterintuitive. Yet the result is liberating.

So, wherever you are on an idea or a project, if your writing starts to feel boring or stale, I encourage you to sit down and write about the messy part—just to see what happens. Even if it’s only for a few minutes. Give it some air to breathe. Explore the complexity rather than wish it away. You might surprise yourself with what you find.

Thinking of writing a book, but scared to pick up a pen? Let’s talk.

I’m a book coach and ghostwriter specializing in memoir and books with themes of mental health and spirituality. Learn more about me here.