“I’m thinking of quitting,” one of my memoir clients told me recently.

“Oh? How come?” I said.

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

“That’s fair,” I said. “Maybe it’s time to put it down for a while.”

Then, a few minutes later in the conversation:

“Well, there’s a part you haven’t read yet,” my client said, “because I don’t know how to write it.”

“Which part is that?”

“It’s something I’m wrestling with: do I forgive G. for what he did, even if I don’t believe him? I don’t know how I feel yet. It’s messy.”

“Please,” I said, perhaps too emphatically. “Let it be messy on paper. Write about what you don’t know yet. That’s exactly what will make it new.”

✨

Listen:

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—

—we deny ourselves the most important part of writing:

Discovery.

🗺️

Robert Frost said this: “No surprise in the writer, no surprise in the reader.”

When the writer is just rehashing, it lacks a certain glimmer, urgency, realness. Readers pick up on that.

On the flip side, readers can also tell when you’re exploring new territory.

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 (from The Artist’s Way): it leads you straight into the weeds.

It’s counterintuitive. It’s liberating.

📝

So if your writing starts to feel boring or stale, dive into the messy parts. The questions. The part you’ve been avoiding.

Explore the complexity rather than wish it away.
You might surprise yourself with what you find. ​.

If you could use some support and guidance as you head into the weeds of your writing, let’s have a chat. You can schedule a call with me here.

I’m booking coaching clients now and ghostwriting clients for 2027.