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.

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We're just 10 weeks away from a major milestone: the 10th anniversary of Freewrite's launch on Kickstarter.  On December 10, 2014, we introduced the Smart Typewriter, then known as  "Hemingwrite," to the world.
How It Started
In September of 2014, co-founders Adam Leeb and Patrick Paul entered Hemingwrite into the “Insert Coin” hardware competition sponsored by Engadget. Described as a new digital consumer product for distraction-free writing composition, Hemingwrite aimed to deliver a singular focus on a productive writing experience. A decade later, that core mission remains unchanged.
Hemingwrite was one of 20 inventions competing that week, highlighting early-stage hardware startups from around the world that had not yet received funding or shipped to consumers.
"What the Kindle did for reading, we want to do for writing," said co-founder Patrick Paul at the time."We set out to deliver the same distraction-free writing experience of a typewriter with all of the added benefits of modern technology."
Co-founder Adam Leeb added,  "We combined all of the best aspects of the typewriter, theMoleskine, and the computer to create a modern classic."
Althoughthe Hemingwrite concept  didn’t win the competition,  the initial coverage by Engadget led to another press hit and then another and quickly it became a viral sensation around the world. The project was covered in everything from The Wall Street Journal to The Atlantic. Over 125,000 people came to the simple wordpress website at hemingwrite.com and over 8,000 anxiously input their email asking for updates on the project.
Adam and Patrick knew they had something special on their hands but weren’t sure if anyone was willing to pay for this idea or if it was simply interesting. On December 10, 2014 the Kickstarter campaign was launched and immediately the pledge dollars started rolling in. Within 20 hours of launch, the campaign had raised over $200,000! And just like that, the Hemingwrite distraction-free writing tool concept became destined for reality.
How It’s Going
Since that initial launch, we have developed Freewrite into a family of distraction-free writing tools with three distinct models, Smart Typewriter, Traveler, and Alpha. Each has their distinct personality, but the core value of maximizing writer productivity runs throughout. 
In 2020, The original Freewrite Smart Typewriter became part of the Science Museum, London’s permanent Printing & Writing Collection.
The name Hemingwrite was dropped in 2015 and then revived in 2021 with the Ernest Hemingway Special Edition Smart Typewriter in partnership with the Ernest Hemingway Estate. 
We’ve created Sprinter for distraction-free writing in any browser and WTF where thousands of people every week receive a writing prompt and participate in Writing Time Friday. 
The community's achievements over the past decade have been  astounding:
  • Freewrite users have created over 600,000 documents
  • Collectively,users have written more than 605 million words (equivalent to over 6,000 novels!)
It’s hard to believe that it’s already been 10 years but it also feels like we are just getting started.
To kick things off:
One Year Warranty: Now Standard
We are extending our warranty that covers manufacturer’s defects to a full year on all Freewrite devices. This means you can enjoy your Freewrite with even greater peace of mind, knowing that we've got you covered for an entire year. 

For more information, please visit our dedicated article on our new warranty policy here: Introducing Freewrite's New 1-Year Warranty: Our Commitment to You
Thank You
As we reflect on 10 years, we're filled with gratitude for the amazing writers who have made Freewrite an essential part of their process. Your passion has shaped our products and fueled our mission.  
Here's to the next decade of your writing success!
 
- The Freewrite Team
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As of October 1, 2024, we are extending our standard warranty that covers manufacturer’s defects to a full year on all Freewrite devices. This means you can enjoy your Freewrite with even greater peace of mind, knowing that we've got you covered for a full 12 months from the date of shipment. We’re even retroactively applying the warranty extension to purchases made this year.

Here is how our new 1-year warranty will work:
  • Beginning October 1, 2024, all new purchases now have a 12-month warranty standard from the shipment date.
  • All device purchases made in 2024 will now have 12-month warranty coverage from the shipment date.
    • For example, if your device shipped on March 1, 2024, your warranty would have expired on May 30, 2024, but will now expire on March 1, 2025.
  • If you purchased an Extended Warranty in addition to your device in 2024, you will receive both the new 12-month standard warranty coverage from the date of shipment, as well as the additional coverage period from your paid extended warranty.
    • For example, if your device shipped on March 1, 2024, with a 2-year Extended Warranty:
      • Your standard warranty now expires on March 1, 2025, instead of May 30, 2024.
      • Your 2-year Extended Warranty coverage will begin on March 1, 2025, and continue until March 1, 2027.



Your trust in our products is paramount to us, and this warranty extension reflects our dedication to your satisfaction and our confidence in the quality and reliability of our devices.

Thank you for choosing Freewrite; we look forward to serving you for many years to come. Write on!

 

- The Freewrite Team



Important Notes:

  • For devices purchased in 2023 or earlier, the original 90-day warranty applies, in addition to any paid Extended Warranty coverage.
  • If you purchased your device in 2023 or earlier, without an Extended Warranty, unfortunately, your warranty has now expired.
  • We are unable to offer refunds for prior out-of-warranty repairs.

 

Useful Links:

Official Freewrite Warranty Policy

Warranty Support Doc