How Do You Know When It’s Time to Stop Rewriting?

How Do You Know When It’s Time to Stop Rewriting?

Too often writers—both amateur and professional—get stuck in the rewrite cycle. Here’s how to adjust your mindset and break out of it.

Klosterman’s Dream of Forever Rewriting

On a recent episode of Filmspotting (one of my favorite podcasts), the author Chuck Klosterman (one of my favorite writers) appeared as a guest. One of the hosts asked him this question about his new book:

“How on earth did you know when you were done writing this book?”

Here’s Chuck’s reply…

“If I could, and if there was a perfect world where every year somebody put a million dollars in my checking account, and all I had to do was keep working on and rewriting ‘Fargo Rock City’ and have it never be published, that would be my dream. I would just love to have that first book and just write it over and over and over again, and have no one see it but myself, but also be rich.”

To some, Klosterman’s dream scenario may seem like a nightmare—a repetitive Sisyphean task where you’re constantly pushing the boulder without ever reaching the top.

But to most writers, this idea makes absolute sense.

Shattering the Myth of the Written Word

The myth is that a piece of perfect “finished” content actually exists. From articles and blogs to websites and video scripts, I’ve probably written thousands of different pieces. And there’s not one piece I couldn’t go back and rewrite right now and make it better.

That has nothing to do with the quality of work I turned in. I produce the best content I can every time I take on a project. But, like a lot of writers, I’m never 100% satisfied. Especially when viewed through the prism of time, I always believe I can make any piece of content better.

Forget About “Perfect”, Focus on “Done”

The key to rewriting success is to abandon the idea of achieving perfection. With copywriting, perfection doesn’t exist. As time passes, even writing you think is perfect when you publish it will begin to crack with imperfections.

My guess would be if you could somehow show great American novelists like Hemingway, Faulkner, or Salinger their “classic books”, they would point out dozens of flaws (even if we can’t see them).

Rather than perfect, aim for complete. Ask most business professionals and they’ll tell you “done” beats out “perfect” any day of the week. Because at least with “done”, you have something to work with.

When It’s Time to Stop Rewriting and Hit Publish

I think Klosterman said it best in his appearance on Filmspotting: “At some point you just say, hey, this is never going to be done, but I’m calling it done and here we go. That’s just how it is.”

That is just how it is: You either hit a deadline or reach a point when the piece is mature enough to send it out into the world. Sometimes you just have to hope you did a good job raising them and let your babies go.

My general rule of thumb is that it’s time to stop revising and rewriting when:

(1) your structure is sound,
(2) you’ve hit all the key concepts you wanted to,
(3) there’s relative clarity to the piece, and
(4) it’s been thoroughly proofed for spelling and grammar errors.

A Final Word…

If you’re stuck in the rewrite cycle, ask yourself: Am I saying everything I want to say? If so, you’re probably in good shape. If not, then what are you missing? If you’re just getting hung up on picking the right adjectives or adding in additional details, it might be time to wave goodbye and pull the trigger.

That’s the best advice I can give you… At least until I rewrite this post again.

Shad Connelly

I'm a Pittsburgh freelance copywriter and communications consultant. I develop online marketing content to define your business and strengthen your brand. Reach me at