I'd discarded two-thirds of Smartcuts by the time the manuscript went to press. Several of my initial hypotheses were disproven by the time I finished, and half of my first draft went into the trash. That was part of the process, as I was embarking with a mission, but not a roadmap. 

Because I started the book with a question and not answers, I wasn't exactly sure what I'd find during the research process. But I wanted to put boundaries around my research and not stray too far from a cohesive theme. I also wanted to complete the book faster than average (in line with the theme of the book). So I designed some creativity-encouraging and simplifying constraints for myself (the theme of Chapter 8!) in my outline process, while allowing for surprises during the research process.

My outline process was essentially what a professor named Randy Ingermanson calls "the snowflake method." He teaches fiction, but the advice he gives in this article applies well to narrative nonfiction. The idea is to start as small as possible, and build an increasingly complex outline step-by-step:

Step One: The One-Liner

The first stop in outlining the book that would become Smartcuts was the back pages of The New York Times Book Review. I had a premise, but my ideas were still coming together. I thought of the book as an adventure in which I'd be taking a reader along with me. But I knew I needed readers to actually decide to come along for it to be worth the time and effort. Thus, I needed to be able to sum the book up in a sentence.

So, I analyzed the one-line descriptions for several months' worth of New York Times bestsellers. A book worth passing along (or that's possible to pass along via word of mouth, which is essential) needs to be able to be summed up quickly and in everyday terms (exactly like the NYT list does with its descriptions; the Book Review has pretty short and hype-free descriptions—not necessarily exciting, but easy to describe). I also needed to be able to sum up the book for myself, to crystallize my swirling ideas into a theme that I felt good about. I looked at all of my back issues of the NYT Book Review to see how hundreds of bestselling books billed themselves. I was looking both for patterns and inspiration.

Then I spent several hours crafting my own one-liner. What would it say if my book was on this list? I filled several notebook pages over the course of a few days. It was like painting the same picture again and again until it felt right. Here are the two variations I finally narrowed my sentence down to:

  • How the world’s most innovative people and businesses get to the top faster than average.
  • How some people do incredible things very quickly in business and life.

Now, these were still drafts, but through the sentence-writing process I had gelled on what was unique about my concept: I wasn't interested in just success (there's lots of books out there about success), but in rapid success. Beating the average. The ones who break the "rules" of success.

Step Two: The Back Cover Description

Next, I converted the one-liner into a couple of paragraphs. Something you'd see on the back of a book jacket, or in the description on Amazon. I spent a few hours on this as well. It was a repeat of my one-liner, but with more detail.

Step Three: One-Page Abstract

So after the jacket copy, I wrote a page-long summary. What you might find in an abstract, or on the inside flaps of a hardcover book. At this point, however, legitimate flap copy would have specifics and teasers to pique interest. I had done a lot of research on my concepts already, but hadn't started, say, trying to get interview access to most of the "superlatives" on my list. So for the purpose of this exercise, I was writing pretend copy—pretending that I already had interviewed Marissa Mayer (youngest Fortune 500 CEO at the time) and had already dug into the case studies I was hoping to get. 

During this stage of the process, I picked up a bunch of books—top-sellers only—to look at how they were structured and the balance of narrative, research, first-person, exposition. I observed a spectrum of styles, from heavily research-and-coined-concept-driven titles like Good to Great on one end to fuzzy-anecdote-driven books like The Success Principles on the other end. I decided that I wanted to be somewhere in the middle: not dry, but still scientific; narrative, but rigorous. I studied examples of authors who pull this off well—folks like Charles Duhigg, Susan Cain, Chip and Dan Heath, and Maria Konnikova. (Notice that these are not purely business writers, either. I figured that popular science was a great place to draw sideways inspiration.) I wrote out abstracts of these books to sort of reverse engineer how Duhigg, et. al. might have described their projects. This helped me refine my own abstract.

Step Four: The Hollywood Pitch

I had now a description of a pretty great sounding fake book. Now that I'd fleshed out my concept a little bit, I stepped back and created a "Hollywood pitch" for the book—essentially going back to the one-liner, but even shorter. The idea of a Hollywood pitch is to explain your book (or movie, etc.) in three or four words, using another book (or movie) as a comparison. Here are a couple of famous ones:

Jaws in space (Alien)

Die Hard on a bus (Speed)

With both of these, you instantly know what to expect. Of course, neither of these movies was that much like its comparison film, but this kind of pitch helps producers and studios buy into a concept quickly. There's also a huge benefit to using an enormously popular title in your pitch comparison: you borrow a little bit of brand equity from it. (Coincidentally, I ended up talking about borrowing brand equity in Chapter 1 in the story about the good/bad US presidents!)

I wrote a grip of Hollywood pitches for my book. Eventually, I settled on one:

Outliers on speed.

Malcolm Gladwell is a gifted writer—I'm jealous of the way he speeds readers along and keeps them guessing even when addressing well-known topics—and Outliers has been on the bestseller list for years. By invoking Outliers, I could do two things at once: 1) Convey that this would be a narrative- and research-driven nonfiction book; 2) Sum up my one-liner in 3 words.

I began talking to people about my idea using this pitch, and actually did so when I spoke to Malcolm himself about the book!

Note: It was at this point that I started talking to literary agents. I sat down with several, simply to seek advice on the process and to learn what publishers would want to see in a first time author like me. The side benefit of this, of course, was that I got to practice the pitch. Before long, I got an offer from a top agent based purely on this pitch. (Of course, my journalism pedigree and connections helped, too.)

Step Five: Insane Note Card Exercise

I now needed to get into real details for further elaboration of my outline to make sense, and to build a proposal that publishers could get excited about. So I stepped back and did a brainstorming exercise. I bought a couple packs of 3x5 note cards and wrote one idea on each: questions I wanted to answer, concepts (success myths, potential answers), stories (often generic like, "a story about x"), characters (the superlatives from my initial list), and miscellany. 

I had a hundred of these cards. Many ended up being rubbish. I grouped the cards on my living room carpet in logical clusters, then regrouped them in different clusters. I tossed cards that didn't make sense. I regrouped them again. After making each grouping, I wrote a bulleted outline on paper to document it. 

Again, I knew that the exact ideas and answers and stories in my notes wouldn't necessarily end up in the book. I was exploring concepts to follow up on. Eventually, I ended up with three different outlines that I actually liked.

Step Six: Minimalist Chapter Outline

At this point, I started seeking feedback. The most helpful was my agent, Jim. I showed him my outlines, and he made a case for one in particular. I shuffled that outline a bit and produced a refined bullet list of the arc of my book. Essentially: Nine chapters, each with a primary question, a hypothesis, and a host of people to interview, academic research to dig up, and original reporting to be done. 

This was about a page long, composed of sentence fragments. I ran this by my agent, too.

Step Seven: Fleshed-Out Chapter Outline

Next, I put some meat on the bones of each bullet. I wrote them out in conversational sentences and paragraphs, until I had, essentially, a summary that read nicely from top to bottom.

Step Eight: Two-Page Pitch For Each Chapter

I showed Jim my outline, and he suggested that I next write a full-fledged magazine-style pitch for each chapter. "Write pitches as if you were proposing each of these as a feature story for one of the mags you write for." So, I built each chapter into a compelling sales pitch. As with any magazine pitch, I had to show the following:

1) Thesis: What questions did I plan to answer with this story. What answers had I found, or what hypotheses was I planning to test?

2) Access: What sources would I use, and how would I get to them? Who did I already have committed to be interviewed? Etc.

3) Story arc: How would I weave the narrative elements together?

4) Why now? Who has already dug into this story, and how will mine be different than what's out there? How will this story be non-obvious and unique? What value will I add to the world with this story?

I went over each of these with Jim in person, and he gave me notes just like an editor. I spent the weekend revising them and turned in a second draft.

Note: I highly recommend this process of treating your agent like an editor and driving a rapid feedback cycle (Chapter 3!) during the early stages of the outlining process—if you have an agent that is up for it.

Step Nine: Finish The Proposal

Finally, I paired my chapter pitches with the standard book proposal sections for marketing plan and author's story, and Jim and I pitched publishers. I was thrilled to sign with HarperCollins less than a week later, which is blindingly fast! I was floored.

The Harper editor had some suggestions for additional elements to add to my outline, and asked some provocative questions that helped me drive my research and writing process.