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.

Recommended articles

More recommended articles for you

April 11, 2025 5 min read

Freewriter Britt Gondolfi has an important message: people need to put down their phones and LOOK UP. The medium she chose to get this message across? Pigeons and poop jokes.

Find out how Britt and her BFF (who happens to be her illustrator) took a silly song and turned it into a book deal.

April 11, 2025 2 min read

Astrohaus, the team behind Freewrite, is an American company. Like many American companies, and virtually all consumer electronic brands, our cost base is global. We work with contractors in Europe, in South America, and in Asia. We purchase components from a global supply chain and assemble our product in China, but make no mistake, we are an American company. The majority of our costs, including goods, services, and payroll, are from the United States. Most of our team lives in the Midwest. I founded this company in Detroit, Michigan, and am still here. I am proud to have built an American company that supports 10+ Americans and their families.

But now we are caught in a trade war that threatens our very existence. A war that was building up over time but has crescendoed to a point that no business owner could have prepared for. As I write this today, we have to pay an additional 145% of the cost of any product made in China as a tax to the U.S. Government.Yesterday it was 104%, up from 54%. In March it was 20% and in February it was 10%. Tomorrow?

Astrohaus is an importer because there is no consumer electronics industry in the U.S. China has emerged over the decades as the world's factory. At first, as a low-cost solution, but in 2025, they are undeniably the best in the world.

Now we are in a pickle because we have established relationships with our contract manufacturing partners that go back to when we started in 2014. Yes, some of the folks we work with today have been with us since the very beginning. They took a chance on us and helped us get off the ground. I have personally spent months on the ground in Hong Kong and China working closely with these folks, whom I now call friends.

Everyone, including our contract manufacturing partners, is helping us explore our options, but the truth is that it is incredibly difficult to move factories. It takes careful planning, huge expense, and much more time than we have.

Unfortunately, we can’t wait to let the trade war resolve itself, nor do we have the advantage big companies like Apple have with a diversified supply base in various countries. We must work with our existing supply base in China, and that means adjusting prices to cover some of our new costs. That's assuming a trade deal gets done, because 100%+ tariffs are simply untenable long term.

As one last hurrah, today through Sunday we will be keeping prices as they have been. Get them while they last.

On Monday, April 14, we will be raising prices. Not because we want to, but because we have to.Thank you for standing by us over the years. We aren’t going anywhere.

Write on,

Adam

Freewrite Founder & CEO

April 10, 2025 4 min read

Bryan Young writes for many magazines and online publications. As you get more entrenched within the industry and develop relationships with editors, the process can vary widely. But at the start of cultivating those relationships, it’s usually very much the same. Here's his walk-through of the process.