Behind the scenes of the Don’t Overthink It writing process

My new book Don’t Overthink It: Make Easier Decisions, Stop Second-Guessing, and Bring More Joy to Your Life came out last week, and today I’m taking you behind the scenes of the writing process, complete with lots and lots of pictures.

When I began tossing this idea around, I knew that some helpful information existed on this topic, but I quickly discovered that books about overthinking focused on rumination. I wanted to focus on all the ways I knew overthinking infiltrated our lives: how did that happen, what could we do about it, and why did it even matter?

That last question became increasingly important to me as I continued to write: my primary purpose in writing this book wasn’t to focus on the overthinking itself, but instead on how to put it aside in order to bring more peace, love, and joy into our lives.

When I started playing around with this idea, I brainstormed in a spiral-bound notebook, and then a Google Drive document. As my document grew longer, and the book’s contents became clearer, it was time to create a loose structure.

What would I do without index cards and sticky notes? They were once again invaluable here. I took the information I’d gathered and transferred every topic I wanted to cover and every story I wanted to tell onto index cards, and then I sorted them into possible chapters. The middle chapters looked like this:

The next photo shows what the outline of the whole book looked like at this stage. (As you can see, some chapters were PACKED with content, and some needed fleshing out.) At this early stage, the book consisted of twenty short chapters, divided into two main sections, which I thought about as “the bad stuff” we want to get rid of (rumination, worry, perfectionism) and “the good stuff” we want more of (rituals, simple abundance, splurges).

That structure was never going to work, but I didn’t know that yet.

If you saw the below photo on Instagram, you should know there are 20 chapters represented in that stack of index cards. The final book has 14, but only five of those chapters were ones I originally planned on writing.

The content of this book shifted dramatically as I wrote it. I thought I knew what a book about overthinking needed to address. But as I learned more and more about overthinking, I grew more and more surprised by just how many facets of our lives overthinking touches. And I realized that the first structure I’d created—positive vs negative—made it impossible to effectively address those complexities.

The below photo shows an early version of Chapter 2, including a story I was certain needed to be in the book. (This story is not in the book.) And that program is Scrivener, which is what I use to write my books.

I spent the next six months in the “messy middle”—that stage between first draft and third draft where I wrote and wrote, moved things around, did more research, made TONS of cuts, and moved things around some more.

As I worked, I began to see that in addition to the two sections I’d initially envisioned, this book needed a third section—one dedicated to showing readers how they can lay the foundation for a satisfying thought life.

In the above photo, you can see how I wrote all my working chapters down on index cards, then laid them down on my kitchen island and shuffled them around until I found the structure that made the most sense at the time. If you can read my points, you’ll see that at this point I envisioned the content in four sections:

“essential” strategies to lay a solid foundation
“overcoming” strategies to stop overthinking in the moment it happens
“freeing” strategies to lighten your mental load
“abundant” strategies to purposefully bring more peace, joy, and love into your life

At this point, I felt like I had 90% of the information I needed to create an interesting, useful book—but it still wasn’t in the right order.

There comes a time when I need to get out of my own head and get some external feedback on what I’ve written. When I’m writing, be it a blog post or a book, my biggest question is: Does the page say what I think it says?

Several months before my initial deadline, and before I obsessed any further on nailing the structure, I sent the current draft of my book to three trusted readers. They weren’t professional book people; instead, they were readers who know me well, and who read a lot of books. I wanted to get their take on my book: what did they find most interesting? Where did their attention lag? What did they find confusing? How did the book help them? Did it feel like anything was missing?

Their notes were invaluable. I printed them off, made a bunch of highlights, and dug back into my manuscript, chapter by chapter. I most strongly differentiated two chapters, combined two chapters, and did some moving around. (See below.) If I hadn’t had these genius giant sticky notes, I would have resorted to writing on my walls!

Then I sent my revised version to another handful of readers I trusted and followed the same process: print, highlight, revise. And then I did it again.

Last March, I sent my manuscript to my editor. When I got my edits back, her first comments were about the structure. (I wasn’t kidding when I said that the structure is always the hardest part for me!)

I did more kitchen counter shuffling, and more rearranging with my giant sticky notes, and we finally landed on the final structure, the one that appears in the published book. The chapters had been rearranged so many times at this point that I had to write the final order on an index card to carry around with me so I didn’t forget! It looked like this:

When the structure changes, the content changes—and now that we’d finalized the structure, I turned my attention to making the content the best it could be. This looked like evaluating the flow of every chapter, doing further research to fill in a few perceived gaps, and sometimes, like a little Ben & Jerry’s.

As you can see, I do most of my writing on Scrivener, but when I want to read what I’ve written, I prefer to read on paper.

My editor and I passed the book back and forth a lot at this stage, as we turned our attention from the question of Is all the right information here? to Is this book a pleasure to read?

As the process goes on, the editing gets more and more specific. We’re no longer focusing on which ideas belong; we’re evaluating the quality of the prose, individual word choice, and formatting questions.

As my final deadline drew near, I made myself A LOT of lists laying out what I still needed to do to finish the book. In the below photo you can see that my to do list includes a polish of each chapter.

In this book I also include a fun quote from literature (or in one case, from my friend’s email newsletter) to introduce each chapter. These were HARD to find! (I used the list on the left to track my quote progress.)

Finally, I got to the stage where I evaluated my word selection in the manuscript as a whole. This was the final step before I turned in my manuscript. How many times did I say magical, terrible, awesome, profound? I wanted every word to be exactly right.

And so I used my Scrivener tools to evaluate word frequency, and then I looked at every. single. instance. of words that I may have overused.

Once I turned in the book, I still had to go through copyedits, and then page proofs, where we make sure every word is perfect and every punctuation mark in its right place. I’m grateful for the copyediting stage, and yet I’ll spare you the screenshots on that, you’re welcome.

The book came out on March 3, and a few days before that, three boxes of finished copies showed up on my doorstep.

And the pretty finished copies look like this on bookstore shelves:

I hope you found this peek behind the scenes interesting. I don’t take the writing process lightly: my goal was to write a book that would be interesting, useful, a pleasure to read, and that ultimately would change people’s lives.

I hope you find it does just that.

Thanks for reading,

Anne

P.S. OF COURSE you can now buy your copy wherever new books are sold. Click here for details.

Behind the scenes of the Don’t Overthink It writing process

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Find your next read with:

100 Book recommendations for every mood

100 Book recommendations
for every mood