How I Write Books: A Practical Guide

This is an excerpt from my e-book How to Come Up With All Those Words: A Practical Guide to Writing a Successful Nonfiction Book, from Conception to Publication.

My mom likes to brag about me to her friends, as moms do. She recently recommended one of my books to a new friend. After the friend finished reading the book, she asked my mom, incredulously, “How does she come up with all of those words?” I take this as the highest of compliments. To be honest, sometimes I haven’t been sure how I came up with all of those words, or if I would be able to do it again. People take it for granted, we authors coming up with tens of thousands of words. But it is not easy.

I got my first book deal in 2008. At the time, I had been working as a journalist for 12 years and felt pretty confident in my ability to write a 1,500- to 2,000-word article. But I had no idea how to write an 80,000-word book. I didn’t even know that books were, on average, about 80,000 words.

But I had wanted to write a book for most of my life, so I took the deal. Then I figured out how the hell to write a book.

I’ve written seven books since, all of them published by Big Five publishers. They’ve been reasonably well-reviewed. One was a New York Times bestseller. Most of that outside validation feels hazy, like it happened to someone else or in a movie I saw a while ago. Some days I joke that every book feels like I’m feeling my way through all over again. But the fact is that I’ve learned along the way, misstep by misstep and step by step, how to actually write a nonfiction book. Few detailed how-to manuals for this exist. I have looked, often in desperation! But I’m going to put down everything I know about this process here, so that you don’t have to make the same mistakes I did.

In this booklet I will walk you through everything I’ve learned since that 2008 book deal, through all seven of my books, most of them narrative pop culture histories: Why? Because We Still Like YouSexy Feminism (co-written with Heather Wood Rudúlph), Mary and Lou and Rhoda and Ted, Seinfeldia, Sex and the City and Us, Pop Star Goddesses, and When Women Invented Television. I will walk you through conceiving and evaluating your book idea, setting realistic goals for your book, conducting research, outlining for maximum success, writing, editing, and fact-checking. If you complete every step in this booklet, you will make a book!

But first, I want to tell you a bit about my journey, and especially what I learned about what not to do.

That first book of mine was a yearlong series of mistakes. I had written a few bad novels throughout my life, starting in college with what was essentially a fan-fiction romantic comedy about an imagined, grownup, journalist version of me interviewing an imagined, apparently straight version of George Michael and falling in forbidden love. (Something about how journalists shouldn’t date their subjects, etc.) I had written a promising-in-parts novel more recently, in my late 20s, circa 2004, loosely based on my own travails working at Entertainment Weekly and calling off my wedding to my college sweetheart. It was promising enough to get me an agent, but not promising enough to sell.

A few years after that, in 2008, I wrote an essay about that calling-off-my-wedding experience that appeared in an anthology and got the attention of a different agent, who approached me about working together. I liked the idea of starting fresh with a new agent. She soon heard from an editor at Grand Central Publishing that they were looking for someone to write a nonfiction book about The Mickey Mouse Club. I had written several articles at Entertainment Weekly about then-current Disney stars such as Miley Cyrus and Selena Gomez, so it wasn’t completely out of my area of expertise.

Some of the most valuable lessons I learned from writing this book, which would eventually be titled Why? Because We Still Like You, were lessons in how to conceive an idea, before any writing begins. Of course, I learned most of these the hard way, by messing them up, or, at best, stumbling through them. Later I’ll walk through some examples from subsequent books to talk about the entire writing process as it moves forward toward a finished manuscript. But it’s worth mentioning these Why? Because We Still Like You lessons that you can use right away, while you’re thinking through your book idea.

1. Know your audience.

This was a slightly unique situation in that I was working with someone else’s idea. But this fact clarified some problems that might have been harder to spot if this were my own passion project. First up: this was a subject for a book, but it was not really what I’d consider a book idea yet. That’s because when I sat down to write an outline for how I’d propose tackling this subject, a key question immediately loomed: There had been three Mickey Mouse Clubs, throughout history. There was the iconic mouse-ear-and-sweater-wearing one in the 1950s with Annette Funicello in the cast. There had been a short-lived revival in the 1970s that included Lisa Whelchel from The Facts of Life. And there had been the 1990s Disney Channel version that was rife with future superstars: Christina Aguilera, Britney Spears, Justin Timberlake, and Ryan Gosling among them.

I realized as I tried to start writing that we had to either pick one to focus on or treat this show as a historic artifact worth explaining on its own, even to people who weren’t fans. In retrospect, I realize I could have taken the latter approach, but it would feel colder and more distant in the writing, and it honestly would have been even harder to market. (Not that I was thinking about that just yet.) I wanted a clear picture of whom I was writing for. So I asked, assuming that we didn’t want the 1970s flop to be our focus: Did we want to be for fans of the 1950s version, or fans of the 1990s version? I prayed for the ’90s, which was both in my lifetime and very aligned with my lifelong fandom of and interest in Britney and Christina. (I’m Team Britney if forced to choose, but I love them both.) Alas, Grand Central chose the 1950s. It turned out the idea came from their publisher himself, who was a fan of the original. So it was that I would be learning all there was to know about the 1950s Mickey Mouse Club, which I was very much not alive for. But at least now I could picture my audience more clearly: It looked a lot like my dad, who was born in 1942.

2. Have a clear vision for the overall book.

This is another thing you take for granted when reading a book, but don’t realize how much thinking goes into it for the writer. Again, we were starting with someone else’s idea: The editor had kind-of mentioned that part of the inspiration for this idea was the very popular, very thorough recent oral history of Saturday Night Live, Tom Shales and James A. Miller’s Live From New York. Awesome book, but, again, my magazine instincts kicked in just enough here for me to foresee problems with the oral history format.

For starters, I am a snooty writery person who likes to write. Oral histories are great, but I have just enough of an artiste in me to want to spend time crafting sentences and telling the story my way, with my analysis and story structure. You absolutely can do some of these things in an oral history. I just didn’t want to.

But another, more practical problem was that I already knew two of the key mice were unlikely to be able to participate in an oral history format: Darlene Gillespie, one of the show’s breakout talents and Annette’s sometime rival, had run into some fraud-related legal troubles in adulthood and had done a bit of prison time, so she didn’t seem like a sure thing. And Annette was suffering from quite advanced multiple sclerosis, so she was also unlikely to be able to do an interview. If you choose a narrative approach instead of oral history, you can write around holes like this, filling in with quotes and recollections from interviews they’ve done in the past. So I went with narrative, which was generally a good decision, even if the publisher for some reason decided to label it an “oral history” in the subtitle anyway.

3. Have a model.

I didn’t do this, but I wish I had. I sort-of had Live From New York as a narrative model, but I should have chosen a book that was closer to what I was actually trying to do. There were just fewer of those back then — in 2008, narrative books about TV shows were just not done, and books on individual films were sparse. Michael Davis’s Street Gang: The Complete History of Sesame Street would have been perfect, but I didn’t find that book until after I had finished Why? Because We Still Like You. For every book since, I have had specific role models that I’ve looked to whenever I was stuck, whether I needed a model for an overall book structure or a specific chapter or even a way of incorporating quotes and details. For instance, before I wrote my next book, a history of The Mary Tyler Moore Show, I pored over Sam Wasson’s Fifth Avenue, Five A.M.: Audrey Hepburn, Breakfast at Tiffany’s, and the Dawn of the Modern Woman. I analyzed every chapter, every reference note, and then built my book from what I learned.

4. Have an outline: the more detailed, the better.

I did have to make an outline to get the book deal. But book proposal outlines usually have chapter summaries that run just a few paragraphs long. It’s easy to write a paragraph or two that sound grand — grand enough, even, to get the book deal — but aren’t really enough to support an entire chapter’s worth of story. Sometimes two paragraphs are just two paragraphs.

The more you can flesh this out ahead of time, the easier your job will be when it comes to writing. Of course you can’t do all of your research ahead of time (we’ll get to that later), but you can do enough with Google alone to piece together, based on information that is already out there, what a chapter might truly entail. Keep in mind that breaking that 80,000-word goal into ten to twelve chapters lands you at a chapter length of 6,000 to 8,000 words. Lots of words. What will they say?

If you’re working with an editor and publisher on this project — that is, if you’re going with traditional publication instead of self-publication — it’s good to show this outline to your editor and agree on the major points before you go off to research and write. You don’t want to spring too many content-related surprises on your editor when you turn in your manuscript. This only leads to editorial pain and heartbreak later. If everyone agrees on an outline, you can always refer to it later to negotiate new material and approaches. But it’s best that everyone starts literally on the same page.

For a step-by-step walk through my entire book writing process, from testing your idea to researching, outlining, writing, and editing, check out How to Come Up With All Those Words: A Practical Guide to Writing a Successful Nonfiction Book, from Conception to Publication.

Jennifer Keishin Armstrong’s writing takes readers behind the scenes of major moments in pop culture history and examines the lasting impact that our favorite TV shows, music, and movies have on our society and psyches. She investigates why pop culture matters deeply, from The Mary Tyler Moore Show and Seinfeld, to Sex and the City and Mean Girls, to Beyoncé, Taylor, and Barbie. She has written eight books, including the New York Times bestseller Seinfeldia, When Women Invented Television, Sex and the City and Us, and So Fetch.

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