The 5 Biggest Writing Mistakes According To A New York Literary Agent

Plus, how to succeed as a writer in a world of AI

One time when mama was alive she handed me a little plastic container of gold chains that were tangled up. She asked if I could separate them for her and I did but seems to me our thoughts are often like that. Sometimes they’re all messed up together.

Writing is often how we untangle our own thoughts.

Joan Didion would have agreed. She wrote a book called “I Write To Find Out What I Am Thinking.” In that book, there’s an essay called “Why I Write” and she says this:

“I write entirely to find out what I'm thinking, what I'm looking at, what I see and what it means. What I want and what I fear.”

Let me tell you what I fear.

I fear a world in which no one cares about writers, about artists, about creators or creative people because who needs them when AI can do it faster and cheaper?

I fear a world where we can’t tell human art from AI generated art.

I fear a world where ChatGPT or Claude or DeepSeek from China strings together words that get more love and appreciation than words written by a human.

We already live in that world.

When ChatGPT launched, it only took two months before it had a hundred million users. You know why, right? Because most people can’t write that well. So ChatGPT gave them the words and made them pretty and they say yes, that’s what I meant, and like Kerouac’s fireworks, other people read the words and said oooohh, ahh.

Readers can’t tell the difference. Did you know that? We think we can. But we can’t.

To be more clear, no one is going to read my writing or any seasoned writer and think it’s AI. They don’t think that. But the other way around? People absolutely do read pieces written by ChatGPT and think it’s written by a human.

Study after study after study shows humans can’t tell AI from human writing anymore. Even linguistics experts cannot accurately tell the difference anymore. I see this on Medium all the time. See people saying they can tell the difference and then I see those same people commenting on AI generated posts like a human wrote it.

But the world of AI isn’t the sum total of the world we live in.

There is that world, yes, but there’s another world, too.

A world where people care about putting their own words on the page. People who care about choosing their words and stumbling and editing over and over to figure out what they think instead of letting a computer program reach into it’s belly and find the words for them. There are still people who care about the craft of writing.

Those are the people for me. Those are my people.

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Noah Lukeman is one of those people. He founded a New York literary agency back in 1996. He’s represented hundred of authors in book deals with major publishers. His authors include winners of the Nobel Peace Prize, the Pulitzer Prize, National Book Award finalists, the PEN Award, the American Book Award and so many others.

Before he launched his own agency, he got into publishing as an intern in the Editorial Department of William Morrow back in the nineties. In six months he represented seven figures in sales for the agency. Because of the books he thumbed-up.

I’m telling you this so you understand that he has an eye for what’s good.

But no. Let me rephrase that because it’s not accurate.

It’s not that he has an eye for good.

He has an eye for what isn’t bad.

Because here’s the thing about writing. There’s no such thing as good. Good is subjective. We like what we like. Maybe you like romance, I like dragons. Maybe you hate Hemingway and love Stephen King. Maybe it’s the other way around.

But bad writing? It’s not subjective. Know why?

Because writing is a journey. First we write badly, and then we write a little better and little better and finally we find our voice and grow wings as a writer.

So when he looks at books, he can see which writers have put in the time, found their voice and don’t make the mistakes that novice writers make. One thing a lot of people don’t realize is that our story and the words we use to tell it with aren’t the same.

There’s a reason I’m telling you that. Here, on Substack.

Because every day — every day, without fail — I go to Notes and see people shouting tips and tricks to get seen, get more viewers, and every time I see those I want to say nevermind the tips and tricks. Work on writing better. Stronger. Clearer.

Because when your writing is strong, when you find your voice, people engage.

Engagement is the key to the universe here on Substack.

When people engage, the algorithm falls in love with you and looks at you with lovey dovey eyes and says well hello stranger, want more of those views?

And all those tips? They’re about getting traction on Notes, and it’s absolutely true that you can post a Note that goes viral and gets 15,000 hearts but if only one percent of those people sign up to read what you write, then how did that help you?

I say that from a place of experience. It took me over five years to get 2000 readers. Five. Years! I had to find my voice.

People using AI? They have no voice.

They never will. ChatGPT doesn’t have a voice.

ChatGPT and every AI out there works essentially the same. AI ate the whole internet and the voice of the output it generates will change from piece to piece depending which writers and which works they dip into to get the output to match the query.

But real writers? Have a voice. Or will, when they hone it.

And if you’re a human, writing from the soul, caring about your words and the craft of writing — that’s what I want for you. To find your voice and your wings and have the algorithm fall in love with your words so it will bring you your people.

It’s why I’m going to sum up Noah’s book in five short points.

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After a few years in the industry, Lukeman said he discovered that he could throw books in the slush pile faster than anyone. Only took 5 pages to say yes or no.

It’s pretty wild if you think about it.

Someone writes an entire book, he reads five pages and says nope. Throws it on the pile of rejections. So someone can send a form letter to the poor sap, break their heart. Five pages. He says the glaring mistakes people make show up instantly.

So he wrote a book called The First Five Pages.

When the book came out, the Editorial Director of Kirkus Reviews said it should be read by all novice writers. His insights on the craft of writing are why he’s been a guest speaker on the subject of writing at Harvard, Columbia, Stanford, Juilliard, and more.

His book doesn’t tell writers what to do.

It tells them what not to do.

I read the book and what occurred to me is it’s not just for authors. It’s for all writers, no matter if you’re writing a book or an essay on Medium or Substack.

According to the book, here are the top 5 mistakes writers make.

— A weak opening
— Rambling lack of focus
— Lack of progression or pace
— Overuse of adjectives and adverbs
— Use of tropes and cliché

You’ve probably heard those a million times, but he makes an interesting point. He says it’s not so much the “things” themselves, but that they show lazy writing.

Take cliché for example. A cliché is just a shortcut for saying something. But writers are supposed to bring a unique way of seeing to the table, and tired old thinking is the opposite of that. Don’t tell me you gave a hundred percent. Tell me what you gave.

Plus? Cliché isn’t just tired old phrases, they’re also tired old ways of looking at the world. Tropes. He says they’re lazy because they are. Same with adjectives and adverbs. We use them because we didn’t think of the word we really wanted.

Writing online, I think the first three are biggest. Weak openings, rambling and slow pace. I honestly don’t think the average reader cares about adjectives or adverbs or even cliché for that matter. Picky readers maybe, but not average readers.

But what I found interesting is he said they travel together. If you’re making one of those mistakes, you’re probably making more than one of them. The book isn’t an easy read. It’s written in a formal and almost academic style, but it’s wildly enlightening because he explains every mistake writers make.

The key is identifying which mistakes we make. We can’t fix what we don’t see.

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Philip Pullman said after food, shelter and companionship, stories are what we need most in the world. I agree with that. We are hardwired for story. Even now, in a world filled with AI. In a world where 57% of the content on the internet was written by a robot we still long to read human stories.

AI is everywhere. On Medium, it costs writers actual money out of pocket. Because writers don’t follow the rules and do put AI generated content behind the paywall and it gets reads and as a result, real writers struggle. On Substack, it doesn’t cost us money because there isn’t a shared pay pool. But it does cost us views.

I can’t stop anyone from using AI to write stories if that’s their thing. I can’t.

One thing that gives me comfort is that even though we can’t tell the difference between human and AI, people want to support human writers. They do. Study after study shows that, too. I wrote a piece on Medium about people who liked AI poetry better than human and when they found out it was AI they were disappointed.

But I can’t stop caring about the craft of writing. I can’t stop caring about human stories. So I write about writing from time to time because I believe honing our skills and finding our voices is the way we shine so bright we rise above AI.

Also? If there’s any of those five you’d like me to know more about, let me know in comments. You’d be surprised how much of my writing starts in comments here. :)

After nourishment, shelter and companionship, stories are
the thing we need most in the world. ― Philip Pullman