Stop Overthinking Your Book (Here’s How)

“Stop overthinking your book.” 🤔

I often give authors this advice. 

It’s good advice. It’s what many people need to hear.

But sometimes, I feel bad when I say it aloud because I know hearing it is not always useful — not on its own anyway (I mean, there’s a reason I wrote a whole book about it).

So much of the advice you get about writing a book is like this, though. 

Write during the time of the day when your mind is sharpest.

Write every day, even if it’s just a sentence.

Don’t let the perfect be the enemy of the good.

These are all fine pieces of advice, but if you could simply decide to stop overthinking your book, you would have already done it.

There’s a reason no one is ever bowled over when I suggest they’re overthinking. It’s not some big revelation. You probably already know you’re overthinking. What you don’t know is how to stop.

So let’s talk about that.

First, a question: Where are you overthinking?

Not all overthinking looks the same, and what’s getting in your way matters for figuring out what to do about it.

Maybe you have a soft spot for research. You love going deep (and your clients value your depth). You find yourself writing one sentence and then disappearing down 10 rabbit holes. 

I get it. It’s hard for me to write anything without needing to verify a statistic, checking the etymology of a word, or looking up the name of the ape Jane Goodall befriended (it’s Koko). 45 minutes later, I’ve read three different articles about chimpanzees, thought of two new objections I want to address, and found a new pair of sandals on sale, but I haven’t written a word.

Maybe it’s your inner critic. Every time you make a bold claim or say something a little controversial, a voice in the back of your head starts asking: Can I really say this? What if people disagree? Who am I to write this book? So you hedge. You soften. You go back and qualify the thing you just wrote, then qualify the qualifier. Or worse… you go play Candy Crush.

Maybe it’s the outstanding questions. You sit down to write and your brain gets to work generating a list of questions you haven’t answered yet. How should I publish this book? Has [insert bigwig in your field] already made this point? What if I forget to include something important? How does [insert name of author friend] describe her book on Amazon? These feel urgent. They feel like things you need to resolve before you can write with any confidence. So you go looking — and now you’re 3 hours into a competitor analysis when you were supposed to be drafting Chapter 2.

All of these are different flavors of overthinking. And the reason they’re so effective at derailing you is that they all feel like legitimate work. The research matters. The critique might have merit. The publishing questions will need to be answered eventually.

But not when you’ve cleared your morning to write.

The bigger picture: You can’t see the forest for the trees

What I’ve noticed after observing other writers’ processes closely is that authors who get stuck are almost always either too zoomed in or too zoomed out. They’re either so deep in the weeds of one section that they’ve lost the thread of the whole book, or they’re so focused on the big picture — the vision, the market, the what-will-people-think — that they can’t get themselves to write a single paragraph.

Writing a book requires strategically zooming in and zooming out. And if you’re stuck, that’s a clue that you need to shift your altitude.

I recently realized I wrote Unwritten backwards. I wrote the pre-writing exercises in the drafting process. Man, I could have used them before I wrote the book. Pre-writing, as I see it, is a way to zoom out far enough that writing actually makes sense.

If you don’t have a clear enough picture of where you’re headed, your only choice will be to get lost in the weeds.

Now that you have an idea of the flavor your overthinking takes, let’s look at the steps to stop overthinking your book.

Step 1: Know your audience and the transformation

Before you write a single chapter, you’ll want to get very clear on two things: 

• Who you’re writing for, and 
• What transformation you want them to make.

It’s most helpful if you picture yourself writing to one person, like a particular client. This will make your writing more conversational and it will help you clarify your argument. Ask yourself: 

• What are they struggling with right now? 
• What have they already tried? 
• What do they believe about your topic that your book is going to challenge or confirm? 

When the right reader finds your book, they should feel like you’re speaking directly to them.

Then: What’s the transformation? Your book doesn’t need to be a repository of everything you know. I’ve read plenty of business books that felt like encyclopedias. They weren’t fun to read, and, more importantly, they weren’t memorable.

Instead, think of your book as taking your reader on a journey from where they are (Point A) to somewhere better (Point B) — a ✨magical place ✨where everyone thinks like you do. 

• When they put the book down, what’s different? 
• What can they do, see, or decide that they couldn’t before?

Answering these questions isn’t just a nice warm-up exercise. It is the antidote to the most common form of overthinking there is: trying to write a book that contains everything you know on the subject. 

When you’re clear on your reader and their transformation, you have a handy filter. You know what belongs and what doesn’t. The inner critic asking “can I say this?” gets a real answer: if it serves this person’s transformation? Then yes.

Step 2: Pressure test your idea

I believe book ideas find us as much as we find our book ideas. The trouble is that these ideas aren’t always fully formed when they land in our brains. They often need some incubation time. 

Often what you think is a book idea is actually only a topic. “I want to write about leadership” is a topic. “I want to write about how the way we develop women leaders is actually making them less effective” is the start of an argument — and arguments are what books are made of.

Here’s a quick diagnostic. Can you complete this sentence: My book argues that…?

If you can’t, you’re not ready to write yet. You’re still in ideation mode. And trying to skip ahead to the writing when you still need to ideate can leave you derailed for a long time.

So, once you have an idea, I recommend that you give it a pressure test to make sure you’re in the right lane.

Pressure testing your idea means asking whether 

• It’s too broad (are there actually three books hiding inside it?), 
• It has a real argument (or just a topic), 
• You’re writing for a specific enough reader,
• The positioning is clear. 

Most ideas have at least one crack. The goal isn’t to find a perfect idea — it’s to get clear on where yours needs shoring up before you build on it.

Pressure testing can help you move forward. Instead of sitting on your book indefinitely, you do the big picture work and then you commit to writing that messy first draft. If you’ve been sitting on your book for years, this is the place to pay attention.

Step 3: Create a realistic writing plan

I’ve never been much of a planner (I’m still not sure what I want to do for my birthday, which is coming up this weekend), but I know that skipping the planning can be a major reason authors get stuck. Another reason they get stuck: Overthinking the planning. So it’s important to find a happy medium here.

The happy medium is what I call a Realistic Writing Plan.

To create a realistic writing plan for yourself, you need three things:

1. Timed writing sessions. I recommend that you do a series of at least 3 timed writing exercises. Choose something to write that could end up in your book. Do you regularly write content, like a blog or newsletter? This is great for a timed writing session.

You can start by setting a timer for 10 minutes and when the timer goes off, look at your word count. From here, multiply by 6 to get an estimate of how many words per hour you write. Do 3 of these sessions and take the average hourly word count as your starting point.

2. A weekly word count goal. Once you know roughly how many words you write per hour, the math is simple. A 40,000-word business book — the right size for most thought leadership books — divided by the number of words you write per hour will tell you how many total hours you need to get your messy first draft done. Then, you can figure out how many hours per week of writing you can squeeze in and that will tell you how many weeks you will need to reach your total word count goal. 

I write about 500 words an hour. So if I write for one hour a day, here’s what that looks like in practice across two different weekly schedules:

You may write more slowly than 500 words an hour — especially at first. Do some timed writing sessions to figure out your baseline, then adjust the math accordingly. 

Remember, the goal isn’t speed for its own sake; it’s having a realistic picture of what it will actually take so you can commit to a plan instead of guessing.

3. Strategies for when you get stuck. Those mid-session rabbit holes and inner critic attacks happen to everyone. The difference between writers who finish and writers who don’t is that the finishers have a move in their back pocket. 

Mine is simple — when I notice I’m distracted by a spiral (could be a research rabbit hole, Maude chirping in my ear, or a nagging question that won’t leave me alone), I stop and zoom back out. I leave a note in brackets: [check this stat later] or [is this the right word?] and I keep moving. You can fix anything in the edit, but you cannot fix a draft you never finish.

The promise

If you zoom out before you zoom in to clarify your audience and transformation, pressure test your idea, and create a realistic writing plan, you can write a messy first draft of your business book in less than 6 months (spending about 5 hours per week writing).

Maybe that sounds too good to be true. But the math doesn’t lie. At 500 words an hour, 5 hours a week gets you a complete messy draft in 16 weeks (that’s only 4 months!). And the pre-writing work I’m describing doesn’t delay the writing — it helps you avoid the overthinking traps you’ve been falling into.

“Stop overthinking your book” is good advice. It just needs a how.

This is it.

Want to work through all of this live with me? In June, I’m teaching a 90-minute workshop — So You Want to Write a Book — where we do the pre-writing exercises together: answering your questions, building the realistic writing plan that will actually get your draft done, and coming up with strategies to get you out of the stuck points. If you’ve been sitting on your book idea, this is where you stop overthinking and start writing. Let’s go!

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