TLDR; First time authors outline the initial book; Second time authors start with questions they have and want/need to learn about.
I come from the startup world.
Over the past few years, in the startup world there has been a big pushback against Business Plans. In fact, I had entrepreneur and professor Carl Schramm join me to to discuss his new book "Burn the Business Plan."
Carl's message is relevant for authors too -- startups and new businesses need to be able to quickly iterate based on what the market tells them. As you learn things, you will change and evolve (quickly). Having a 75 page business plan is the opposite of that -- it locks you in and doesn't allow you to be flexible.
Similarly I see the same challenge for authors just beginning working on a book:
Table of Contents = Business Plan
Assumption: You should write out your table of contents before you start writing
"Experts write books."
There's a distinct pressure that comes from deciding to write a book. We tell ourselves that to write a book you need to be smart, have something valuable to say and be an expert. 'What makes me better than the dozens of other, smarter authors out there that are writing books on similar topics or in similar areas?'
One piece of valuable advice I received early on was to create a book proposal before you begin your book. And I agree it's pretty solid advice -- think about what the key aspects of the book BEFORE you invest too much time. Here are the summary sections from previous book proposals I've done:
- An Overview of the Book
- Target Audience
- About the You (ie., the Author, your prior works and your current audience)
- Your Plan to Market the Book
- Competing Books & Titles
- The Table of Contents
- A Sample Chapter or Two
This all looks a bit intimidating -- especially early on -- because it assumes you know a lot. And so many authors ignore or skip the sections like Target Audience ("It's for everyone" or "We will figure that out later") and Marketing Plan ("That's way off in the future"). Instead they fixate on the one thing they believe matters and can control:
- Table of Contents
And so they sit down and begin to write out how they think the book should be structured based on what they know.
The problem is once you write a table of contents, nearly every first time author I've met begins to 'write to the table of contents.' In fact, even I did this in my first book -- laying out two dozen chapters and attacking them one after the other.
The problem was: I became obsessed with the table of contents, rather than learning.
Reality: Too much structure is the enemy early in your book process
Malcolm Gladwell is one of today's most popular authors. But he defies the idea that "Experts write books." A better descriptor for Gladwell is "Curious people write books."
And he never starts a new book by outlining a table of contents.
"The first step in looking for a story worth writing is to read,"Malcolm Gladwell
Gladwell told the Yale Daily News in 2012. "When he finds an interesting author, Gladwell said he reads the articles the author cites in his work. He follows this trail of articles until it leads him to a story that intrigues him. Gladwell compared the process to that of academic research, adding that he looks for a way to 'connect [the ideas] to people outside” of academia'."
Nearly every second time author I've met does the same: they start with a question or questions.
Nir Eyal, author of Hooked and Indistractable, shared with me:
"I start with a personal problem I'm having and then I read every book I can find on the subject to find an answer. And if I'm not satisfied with those answers, I realize I have to write the book."Nir Eyal
I tell authors on day 1: You're not writing a book on what you know; you're writing a book based on what you're learning.
Start with Questions
For a new author, don't worry about being an expert… yet. Worry about becoming an expert through the work you put in on the book.
I urge authors to look for the themes they wish to explore. Themes include:
- What are the key intersection points the book will explore? (Augmented Reality & Sports; Immigration & Success; Food & Social Media)
- What trend is happening that is changing the status quo? (Minority communities changing opinions on mental wellness; leadership in the 'Gen Z' era; parenting in a data driven world)
- What are current controversies today related to the topic? (Social Media's Impact Happiness; NFL's concussion issues)
Turn those themes into questions you want to explore. Then go out and find who is talking about those themes and sub-themes.
And remember this isn't just for nonfiction books -- you'll find that exploring the themes of your novel or memoir are just as powerful. Your underlying themes/plot won't be unique -- and finding people talking about those themes can give you greater understanding. So rely on those insights to deepen your writing.
Listen for Inspiration
Gladwell is right about the importance of stories. Books are driven by stories -- it's what we want to read and what moves us to act.
I urge authors to go out and listen to people telling stories. The best way I find to quickly learn and uncover stories is diving into podcasts. Podcasts are full of rich, robust interviews where hosts know that stories drive listeners. The absolute best way to discover answers to these questions is by listening to compelling individuals tell their stories related to your themes.
- If you're curious about how augmented reality could change sports, find podcasts where startup founders or sports executives talk about augmented reality.
- If you're curious about minority communities and mental health, find podcasts where the guest talks about that subject.
You don't need the 'answer', but you do want to find a collection of stories that begin to reinforce a common refrain or answer. You're looking for a pattern: find 6-10 stories that begin to offer similar insights and takeaways, then you're onto something.
Follow the Rabbit Hole
Not needing to have answers is incredibly freeing -- just explore where things take you.
If you force yourself to follow the table of contents you have now, you may miss something. But once you embrace the theory that you don't want a table of contents (yet), you can let the stories take you where you need to go.
If you are listening to podcasts or watching YouTube videos, follow the suggestions in the "More like this…" section. Take key phrases and insights, and look into them.
Go down the rabbit hole until you decide its where you want to be, or you figure out you need to climb back out.