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Stop Overthinking Everything: Advice for Writers

Annie Cosby
September 18, 2024 | 5 min read

Do you ask yourself the same questions about your current work over and over again, making no headway whatsoever? Or maybe you find yourself sitting in front of your story, mind spinning, making no progress?

This likely means you’re overthinking it.

We spoke with writing expert K.M. Weiland about this common writer problem and how you can overcome it.

K.M. Weiland writes historical and speculative fiction — usually a mix between the two, such as dieselpunk and gaslamp fantasy — so she knows a thing or two about complex stories and themes.

Eleven books in, she also knows a thing or two about writing. That’s what led her to create HelpingWritersBecomeAuthors.com and her acclaimed writing guides, Structuring Your Novel and Creating Character Arcs.

As a self-proclaimed outliner, she was our go-to for a common question we hear from writers:

How do you know when you’re overthinking things? And how do you escape that cycle?

 

AC: First off: You're a plotter, not a pantser, right? That involves a lot of thinking.

KM: I’m fascinated by systems and organization, which is what I study and share on my website and podcast, as well as my writing-craft books. So it's no surprise I’m a plot-forward planner. Outlining is my favorite part of the process.

I write extensive outlines that, in some ways, are more of my rough draft. This part of the process is no-pressure. It’s just a stream-of-conscious conversation with myself as I ramble through the possibilities of my story.

At this point in time, almost twenty years and eleven novels on, I’ve developed an in-depth process, which I’ve written about on my blog and in my book Outlining Your Novel. I start out with general brainstorming, then move on to character sketches, worldbuilding, and finally scene outlines, before starting research (if necessary) and the first draft.

I write extensive outlines that, in some ways, are more of my rough draft. This part of the process is no-pressure. It’s just a stream-of-conscious conversation with myself as I ramble through the possibilities of my story.

AC: It's so interesting that there's freewriting in your outlining process. So where's the line? How does a writer know they're overthinking things?

KM: There is an important distinction between overthinking and developing excellent critical thinking skills. One of the best ways I know to do the latter is to focus on the quality of questions you’re asking yourself.

If you’re asking good questions, you’re not overthinking.

But when you’re just swimming in circles of self-criticism or perfectionism, then that — in my experience — is when you know you’ve crossed the line into overthinking.

Overthinking is almost always the emergent of two different causes. The first is simply a lack of knowledge. When we don’t have enough context to help us ask the right questions, this inevitably leads to us circling the same ideas over and over again, unless and until we find a thread to pull.

The second cause of overthinking is perfectionism. Writers often ask me how they can know when an outline or a first draft is “finished.” My somewhat tongue-in-cheek answer is always, “When you reach the end.”

But perfectionism can make it difficult to know when you’ve reached that point.

But when you’re just swimming in circles of self-criticism or perfectionism, then that — in my experience — is when you know you’ve crossed the line into overthinking.

AC: What are the dangers of overthinking in your writing? What do you risk losing?

KM: Again, it’s a fine line. If we underthink, then we risk producing work that is far below our own capabilities. We aren’t pushing ourselves or looking inside for our deepest truths and most original ideas.

However, creativity is a sometimes capricious state of being. It operates best from within “the zone” — when our brains are in Alpha state, which is the opposite of the busy mind we general experience in Beta.

Overthinking, born of perfectionism, can also send us into discouragement. Continually asking ourselves generic questions that lack useful answers (e.g., “is this good enough?” or “should I tweak this just to see what happens?” or “is my dialogue stupid?”) just wears us out. We never get anywhere useful with such lines of thought, and they almost always end up triggering our insecurities rather than actually improving the work.

Continually asking ourselves generic questions that lack useful answers (e.g., “is this good enough?” or “should I tweak this just to see what happens?” or “is my dialogue stupid?”) just wears us out. 

AC: So how do you stop those lines of thinking?

KM: The first step is simply to keep learning. Broaden your context of storytelling knowledge. The more you know about stories, what works, and what doesn’t, the more intentional you can be in the questions you are asking yourself about your own writing.

You can’t think your way to a good ending if you have no idea of the storytelling principles (such as plot structure) that create a good ending. But you can feed your mind more knowledge, as well as exploring your own storytelling instincts through creative experience.

Part of this growth includes the second step, which is learning to ask high-quality questions. Instead of generic questions, such as those I mentioned previously, strive to activate your critical thinking skills (which, again, is the opposite of overthinking) to ask very specific questions.

This requires growing your ability to truly understand your own instincts. Instead of overthinking, ask yourself what you’re feeling about your story. If you have an uncomfortable niggle, where is it coming from? Is it coming from your own insecurities or from a legitimate lack of knowledge about how to do something? Or is it coming from a specific problem in the story that you can get dig deeper into?

Finally, addressing your relationship with the toxic inner critic is vital. A healthy inner critic guides us toward legitimate growth and improvement, while a toxic inner critic only tears us and our work down. Most overthinking falls into the latter category.

A healthy inner critic guides us toward legitimate growth and improvement, while a toxic inner critic only tears us and our work down.

AC: Couldn't agree more that mastering that relationship with your inner critic is critical to a happy, productive creative life. Any last advice for writers struggling with overthinking?

KM: Don’t overthink the fact that you’re overthinking! Seriously. Take a step back — or maybe even some time off if necessary. Let your unconscious brain take over. It has all the good answers anyway.

And if it just isn’t coming up with what you need, then it probably needs to be fed more information. Take some time off to fill your well by reading whatever feels most pertinent. Answers always come when we’re patient. They’re not always the answers we’re hoping for, but as soon as we ask the right question, the answer will appear.

You can find more writing advice from me at HelpingWritersBecomeAuthors.com, where I publish in-depth posts and podcasts that include the critical thinking and important knowledge writers need to create the context for asking the right questions.

October 12, 2025 4 min read

The winner of the inaugural Freewrite 500 flash fiction competition is Brie Ripley Sparks, with her short story "High Holy Days."

October 12, 2025 2 min read

The first place story in the 2025 Freewrite 500 is "High Holy Days" by Brie Ripley Sparks.

September 10, 2025 3 min read

The Freewrite 500 Writing Contest — Terms and Conditions

Last Updated: 10-09-2025

By submitting an entry to The Freewrite 500 Writing Contest (the “Contest”), you agree to abide by the following Terms and Conditions.

1. Organizer

The Contest is organized by Freewrite, a brand owned and operated by Astrohaus, Inc. (hereinafter referred to as “Freewrite”, “we”, “our”, or “us”).

2. Eligibility

  • The Contest is open to individuals who are 18 years of age or older at the time of entry.

  • Employees of Freewrite, the Flash Fiction Institute, and their immediate families are not eligible to enter.

  • Void where prohibited by law.

3. How to Enter

  • Entries must be submitted through the official entry form before Monday, September 22.

  • Entries must be original works of flash fiction no longer than 500 words.

  • All submissions must be the original work of the entrant.

  • Only one entry per person is allowed.

  • Entries must be written in English.

  • The deadline for submission is 11:59 p.m. EST on September 22, 2025. Late or incomplete entries will not be accepted.

4. Entry Requirements

  • Submissions must be the entrant’s own original work and must not have been previously published, including on personal blogs or social media.

  • Entries must not contain any material that is obscene, offensive, defamatory, or otherwise inappropriate.

  • By entering, you confirm that your submission does not infringe on any third-party rights, including copyright, trademark, or privacy rights.

5. Judging and Winner Selection

  • All eligible entries will be judged by a panel of reviewers affiliated with Freewrite and the Flash Fiction Institute.

  • Judging criteria include length, creativity, and adherence to theme, and overall quality of writing.

  • The winner will be notified via email.

6. Use of Generative AI Prohibited

  • The use of generative AI in the creation of a submission for this competition is prohibited.

  • The organizers reserve the right to disqualify any entry that is suspected to have been generated, in whole or in part, using generative AI tools (including but not limited to text-generating algorithms, large language models, or similar technologies).

7. Prize

  • The winning entry will be published on both the Freewrite Blog and the Flash Fiction Institute Blog.

  • The winner will receive recognition across Freewrite and Flash Fiction Institute's social media platforms.

  • No cash prizes will be offered. Prizes include a Freewrite Traveler, a Words Are Hard writing prompt deck, publication on the Freewrite blog and the Flash Fiction Institute blog, and a free flash gym session hosted by the Flash Fiction Institute.

8. Rights and Usage

  • By entering the contest, entrants grant Freewrite and the Flash Fiction Institute first publication rights. This means Freewrite and the Flash Fiction Institute have a non-exclusive, royalty-free, worldwide license to publish, reproduce, and distribute the submitted entry in connection with the promotion of the Contest, including on their websites, blogs, email newsletters, social media channels, and more.

  • After initial publication, all rights revert back to the author, who is then free to republish or distribute their work elsewhere. However, we request that any subsequent publication acknowledges Freewrite and the Flash Fiction Institute as the original place of publication.

  • The winning author will be credited by name or preferred pen name when their work is published.

9. Privacy

  • Personal information collected during the entry process will be used only for the administration of the Contest and in accordance with Freewrite’s Privacy Policy.

  • Entrants may be contacted by Freewrite regarding their submission or related opportunities.

10. Disqualification

Freewrite reserves the right to disqualify any entry that:

  • Violates these Terms and Conditions,

  • Is found to contain plagiarized material,

  • Is deemed offensive or inappropriate,

  • Is submitted by someone ineligible.

11. Limitation of Liability

Freewrite is not responsible for:

  • Lost, late, incomplete, or misdirected entries;

  • Technical failures of any kind;

  • Any injury or damage to persons or property related to participation in the Contest.

12. Governing Law

These Terms and Conditions shall be governed by and construed in accordance with the laws of the State of [Insert State], without regard to its conflict of laws principles.

13. Contact

For any questions regarding the Contest, please contact us at:
📧 hello@getfreewrite.com.