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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.

November 29, 2025 4 min read

The Great Freewrite Séance: A Ghost'ly Charity Auction Full Terms & Conditions

These Terms and Conditions (“Terms”) govern participation in The Great Freewrite Séance: A Ghost'ly Charity Auction (“Auction”), organized by Freewrite (“Organizer,” “we,” “us,” or “our”). By registering for, bidding in, or otherwise participating in the Auction, you (“Participant,” “Bidder,” or “Winner”) agree to be bound by these Terms.

1. Auction Overview

1.1. The Auction offers for sale a limited number of Freewrite Traveler Ghost Edition units (“Items” or “Ghost Traveler units”), each personally signed and drawn on by a featured author.

1.2. All proceeds, net of explicitly disclosed administrative costs, will be donated to the charity or charitable initiative (“Charity”) identified on each auction item’s page, as chosen by the respective author.

2. Eligibility

2.1. Participants must be at least 18 years old or the age of majority in their jurisdiction, whichever is higher.

2.2. Employees of Freewrite, the participating authors, or any affiliates directly involved in the Auction are not eligible to bid.

2.3. By participating, you represent that you are legally permitted to take part in online auctions and to pay for any bids you win.

3. Auction Registration

3.1. Participants must create an account on the auction platform or otherwise register using accurate, current, and complete information.

3.2. Freewrite reserves the right to verify identity and to disqualify any Participant who provides false or misleading information.

4. Bidding Rules

4.1. All bids are binding, final, and non-retractable.

4.2. Bidders are responsible for monitoring their bids; Freewrite is not liable for missed notifications or technical issues on the auction platform or the Participant’s device.

4.3. Freewrite reserves the right to:

  • set minimum bids or bid increments;
  • reject bids deemed in bad faith or intended to disrupt the Auction;
  • extend, pause, or cancel the Auction in case of technical difficulties, fraud, or events beyond reasonable control.

5. Winning Bids and Payment

5.1. The highest valid bid at the close of the Auction is the Winning Bid, and the corresponding Participant becomes the Winner.

5.2. Winners will receive payment instructions and must complete payment within 48 hours of the auction’s close unless otherwise stated.

5.3. Failure to complete payment on time may result in forfeiture, and Freewrite may offer the Item to the next highest bidder.

5.4. Accepted payment methods will be listed on the Auction platform. All payments must be made in the currency specified.

6. Item Description and Condition

6.1. Each Ghost Traveler unit is authentic, and the signatures, doodles, and messages are original works created by the participating author. These are authors, not artists. By bidding on the Item, you acknowledge that you are receiving a one-of-a-kind unit marked with unique art and messages and you agree to these terms and conditions.

6.2. Because Items are customized and signed by hand, variations, imperfections, or unique marks are to be expected. These are considered part of the Item’s character and not defects.

6.3. Items are provided “as-is” and “as-available.” Freewrite makes no warranties of merchantability or fitness for a particular purpose.

7. Shipping & Delivery

7.1. Shipping costs, import duties, and taxes may apply unless explicitly stated otherwise.

7.2. Freewrite will make reasonable efforts to ship Items within the estimated timeline but cannot guarantee delivery dates.

7.3. Title and risk of loss transfer to the Winner upon delivery to the carrier.

7.4. Freewrite is not responsible for delays, damage, or loss caused by the courier or customs agencies.

8. Charity Donation

8.1. Net proceeds from the Auction will be donated to the Charity designated on each Item page.

8.2. Donation amounts and recipients may be disclosed publicly unless prohibited by law.

8.3. Winners acknowledge that they are purchasing Items, not making a tax-deductible donation to Freewrite; therefore, Winners will not receive charitable tax receipts unless Freewrite explicitly states otherwise in compliance with applicable laws.

9. Intellectual Property

9.1. All trademarks, brand names, product names, and creative materials associated with Freewrite and the Ghost Traveler remain the exclusive property of Freewrite or their respective rights holders.

9.2. Participants may not reproduce, distribute, or publicly display the authors’ doodles without permission where such rights are applicable, except as allowed by law (e.g., resale of the physical Item).

10. Privacy

10.1. By participating, you consent to Freewrite’s collection, use, and storage of your personal data in accordance with our Privacy Policy.

10.2. Freewrite may publicly announce auction results, including Winner’s first name, last initial, city, state/country, and winning bid amount unless prohibited by law or unless you formally request anonymity when possible.

11. Prohibited Conduct

Participants may not:

  • engage in bid manipulation, fraud, or collusive bidding;
  • use automated systems (bots, scripts, scrapers) to place or monitor bids;
  • interfere with the Auction, platform, or other participants

Freewrite may ban or disqualify any Participant violating these rules.

12. Limitation of Liability

To the fullest extent permitted by law:

12.1. Freewrite is not liable for indirect, incidental, special, or consequential damages arising from the Auction or purchase of Items.

12.2. Freewrite’s total liability in connection with these Terms shall not exceed the amount of the Winning Bid actually paid by the Participant.

12.3. Freewrite is not responsible for technical malfunctions, internet outages, system failures, or other issues beyond its control.

13. Cancellation and Force Majeure

Freewrite may cancel, postpone, or modify the Auction due to unforeseen circumstances, including but not limited to natural disasters, system failures, strikes, or events affecting participating authors or the Charity.

14. Governing Law & Dispute Resolution

14.1. These Terms are governed by the laws of Michigan, without regard to conflict-of-law rules.

14.2. Any disputes arising under these Terms will be resolved through binding arbitration or the courts of the specified jurisdiction, as applicable.

14.3. Participants waive any right to participate in class-action lawsuits relating to the Auction.

15. Amendments

Freewrite may update these Terms at any time. Continued participation in the Auction after updates constitutes acceptance of the revised Terms.

16. Contact Information

For questions or concerns regarding the Auction or these Terms, contact: hello@getfreewrite.com.

November 25, 2025 1 min read

This is a great gratitude writing exercise to be done alone or in a group, with people of any age.

How to Play

    1. Designate someone to read out each prompt below. (Feel free to add your own prompts.)
    2. After each prompt is read, set a timer for one minute. (With younger kids, this can be shortened. For older folks who want to freewrite meaningfully, more time can be added.)
    3. Each person freewrites by finishing the sentence and elaborating until the timer goes off. (For little kids, this can be done verbally with an adult recording their answers. Hilarity will ensue.)
    4. Remeber that freewriting — allowing yourself to write with abandon — enables you to let go, tapping into your subconscious to explore your thoughts more deeply.
    5. When everyone is done with all the prompts, take turns going through some your answers. Some people may be eager to share. Others may not want to. Respect their decision.

The Prompts

  • I'm grateful for... [After you've finished this prompt, repeat it five times. Challenge yourself and others not to repeat a singe word with each new answer.]
  • The silliest thing I'm grateful for is...
  • The littlest thing I'm grateful for is...
  • The biggest thing I'm grateful for is...
  • The grossest thing I'm grateful for is...
  • One thing I love about myself is...
  • My favorite thing that happened this year was...
  • My hope for next year is...

This writing exercise has resulted in some sweet answers — and many hilarious ones, too. If you try it out, do let us know.

Write on.

November 21, 2025 4 min read

For the release of Sailfish, our new firmware update for Smart Typewriter Gen3 and Traveler, we created a brand-new boot-up animation to surprise and delight our writers.

We worked with talented Danish animator Mathias Lynge to bring our experience of the writer's journey to life.

We had a blast visualizing the writer's journey in this new way. Our engineers also had a blast (or something less than a blast) figuring out how to adjust this fun, playful animation to E Ink's very tricky specifications. Hello, refresh rate woes! But we think the result is pretty fun.

"The little animation made my day when I noticed. I love a good flourish."

- Freewrite user

The process of creating this animation was long and full of Zoom calls where we deeply discussed the writing process. We were struck through those conversations by how much overlap there is in creative processes of all disciplines.

So we sat down to chat with Mathias about his creative process and what it's like being a full-time animator.

ANNIE COSBY: Let's start with the basics. What kind of art do you make?

MATHIAS LYNGE: I'm a 2D animator and motion designer working freelance with a wide range of clients. The style varies depending on the project, but it’s usually either a hand-drawn look animated frame-by-frame on a drawing tablet, or a more digital, vectorized look made in After Effects.

While much of what I do is commercial work, I try to keep up with my own passion projects as well. That could be a 10-second Instagram loop of a nature scene, or an interesting character design I’ve sketched down with a pencil. It’s there that I get to sharpen my skills and try out new techniques, which often find their way into later client projects.

AC: You often share educational content on social media for other artists. Are you formally trained, or did you teach yourself?

ML: I’m mostly self-taught. I’ve been drawing for as long as I can remember, but it wasn’t until I went to university that I realized drawing could become a career.

When I first heard terms like “motion design” and “The 12 Principles of Animation” I was on a student exchange program at UCSB in California, where I had chosen a class called "Introduction to Animation." It was a big eye-opener for me, and from that point I was hooked.

But it’s mainly been online YouTube tutorials and my existing drawing experience that have taught me what I know.

Now, I have a big presence on social media, where I share my art as well as educational content centered around animation in Adobe After Effects, so I guess you could say that I'm also an animation influencer!

I’ve been drawing for as long as I can remember, but it wasn’t until I went to university that I realized drawing could become a career.

AC: That's actually how I first found your work. Do you have any specific artists who inspire you?

ML:In the world of 2D animation, I have a list of personal heroes that inspire me with their unique style: Reece Parker, Ariel Costa a.k.a. BlinkMyBrain, and Tony Babel, to name a few.

I also find a lot of inspiration from illustrators and painters I discover online, on platforms such as Pinterest. Last year I made a sparkling water animation that was heavily inspired by Cornwall-based artist Gordon Hunt. He makes these beautiful nature-inspired pointillist paintings that capture how light hits the ocean using colorful dots of paint. I tried to recreate that effect using After Effects to bring it to life, and it led me to a whole new way of animating within the program.

AC: Where else do you draw inspiration to create your work?

ML: I’m heavily inspired by the nature and cityscapes around me in Copenhagen, and I find that taking long walks through parks or down the streets of my neighborhood really sparks my imagination.

I’ll often carry around a sketchbook to quickly scribble down an idea or a loose sketch of something I find interesting, such as seeing how the light from a lamppost hits the surrounding leaves, or how the wind moves the tree in a certain way.

Then I’ll think to myself, “I wonder if I can recreate that motion using a specific technique in After Effects?”

I’m heavily inspired by the nature and cityscapes around me in Copenhagen...

AC: What does your daily routine look like as a full-time artist?

ML: It varies a lot, but I’m usually either working hard on a client project or tinkering away with a new animation tutorial for my social media channels.

I love being able to switch between the two, and when I’m going through a client dry spell, I find that staying creative and posting animation-related content helps keep me inspired while also putting things out into the world that may lead to my next client down the road.

AC: What's your #1 piece of advice for animators new to the industry?

ML: Keep experimenting and trying out new techniques. There’s no such thing as running out of creativity, and even though many of the things you try don’t necessarily go anywhere, it’s all experience that adds up and expands your toolbox. It’s a muscle that needs to be worked out regularly.

Plus, you’ll have more awesome animation to choose from when you’re putting together your next showreel or portfolio!

There’s no such thing as running out of creativity...

AC: What's one fun fact about you completely unrelated to animation?

ML:I’m a big sucker for history podcasts, especially if they are about ancient civilizations, such as The History of Rome by Mike Duncan.

I find it fascinating to hear how mankind was able to build such great empires without ever knowing what electricity, cars, or the internet are.

--

Follow along on Mathias's creative journey and find his free educational content on Instagram.

To learn more about working together, find him on LinkedIn or visit his website at www.mathiaslynge.com.

Learn more about Sailfish here.