How To Write The Book Of Your Dreams: An Outrageously Detailed Guide

Behind the scenes of the making of the new book Dream Teams, and how you can make your own book come true. (Including: screenshots, tools, spreadsheets, charts, and bad jokes.)

Ijust launched my third book, Dream Teams: Working Together Without Falling Apart. To celebrate and to pay forward some of the great book writing advice I’ve gotten over the years, I’ve decided to peel back the curtain and do the thing I never did in high school math class: show my work.

Over my 3+ year journey making Dream Teams, I documented my process at every step. I hope that peeking into it can help you with your own book or big writing project one day. I’m going to put together another big post on book marketing soon, but for now we’re just going to talk about making something worth marketing in the first place.

My quest is to share with friends and colleagues the alchemy behind what one critic called:

“The best darn thing I have ever read ever, and I’ve read that essay on kindness Jesus wrote in high school.”

Ok, nobody ever said that. But that’s the feeling you have when you finish a book. It’s exhilarating and awesome!

(For about 45 minutes before the panic of the prospect of someone reading said book sets in.)

The calm before the panic…

This post will walk through the following:

  1. The agony of book writing — and how to get through it
  2. How I do concepting and research planning
  3. My research method(s)
  4. How I do my outlining before I buckle down to write
  5. The scoop on titling and book positioning (this comes before writing for a reason; you’ll see)
  6. How I wrote and shaped the Dream Teams manuscript (including a time-lapse video of me building a chapter in 1 minute using Evernote, Google Docs, and Hemingway!)
  7. Body Armor: editing, fact-checking, and manuscript bulletproofing
  8. My one tip on book cover design
  9. A rundown of my favorite tools for researching and writing

After all of that, you may just end up with something you’re proud to see your name on, like this:

Ok, here we go:

I. The Agony of Book Writing

Perennial houseguest Oscar Wilde was once asked by his host what he’d been up to that day…

“I was working on the proof of one of my poems all the morning,” Wilde replied, “and I took out a comma.”
“And in the afternoon?” the host inquired.
“In the afternoon,” said Oscar, “well — I put it back again!”

Oscar wasn’t slacking. Anyone who’s ever attempted to compose anything longer than a tweet knows that converting the human experience into words is like performing brain surgery with a Slap Chop. With a few notable exceptions (Kubla Khan, The Catcher in the Rye), great literature doesn’t just write itself. And no reader is ever going to think your baby is as cute as you think he is.

“All writing is rewriting,” said John Green

…and every other writer since cavemen scratched on rocks. If you’ve never spent 15 hours going over the same three pages again and again until your eyes bleed, then, buddy, you’re on the wrong career track.

What I’m trying to say is: Writing a book sucks way worse than writing other things. Even if, like me, you love the act of writing itself.

Trust me. Don’t do this if you aren’t willing to roll down one of those awful Chinese staircases naked for your book… and then walk back up and do it again. Cuz that’s what making a book is like.

If you’re ready to do that, though, there are some things that will help…

4 Things To Help Ease The Book-Writing Pain:

  1. Only write a book about something you love so much that you’re willing to talk about it for the next five years. Between the writing and the promoting, you’re going to be in this for a long haul. So if you’re going to write a book, write about something you’re happy to have the majority of your conversations be about for the next half-decade. Being madly in love with the topic will save you LOTS of pain when things get hard.
  2. Take breaks from thinking, before you feel burnt out. Don’t wait ’til you’ve got an epic case of writer’s block to take a breather. In fact, the right time to wander over to Netflix is precisely when you’ve still got something compelling left to say. Your muse is like a ’76 Gremlin. Park that sucker on a hill, and it’ll be so much easier to pop the clutch and bring the ol’ bird back to life one more time if it’s not burnt out.
  3. Try to make the actual thing as fun to read as it is to watch whatever is popular on Netflix right now. Basically: IF YOU’RE BORED, THEY’RE BORED. Remember: only one person thinks it’s cute when your manuscript projectile-vomits mooshed peas. If you are boring you, just imagine your reader!
  4. Drugs. (Fun fact: All the greats did speed!) Okay, the real advice here is I recommend making a diet and caffeine routine—and being strategic about the timing—to optimize your output and minimize your excuses for not pounding out sentences. I actually spent a lot of my actual manuscript writing process in ketosis, which is a diet that, once you get into it, keeps your blood sugar and energy levels pretty stable. This is good, because my personal writing process involves bursts of long writing sprints, and you don’t want a mood/energy rollercoaster to affect something like that.

Lemme put it another way…

— A seventh-grader reads a book just to finish reading it.

— A noob writes a book just to finish writing it.

— But an author? An author weaves words for the sheer joy of it. An author has a song. So she sings.

So sing a song that won’t annoy you two years from now.

(And then edit your song one million times.)

II. Concepting And Research Planning

You know that whole thing about how Michelangelo didn’t carve the statue of David, but instead he just dug into the stone until he “found” him? That’s what creating a good book is like. (I owe that analogy to my agent, Jim. Jim, you’re the best!)

Concepting is about finding the core thesis of the book you plan to write. What’s the underlying thing you’re writing about, the bedrock on which you’ll build your research and narratives?

Or, conversely, what’s the umbrella under which everything in your book lives. Or, what’s the thread that ties everything together?

Whichever analogy is the right one for your particular project, I think the first and most important questions to ask are these:

1. What am I trying to convey to people? And:
2. Is a book the best medium in which to convey it?

Don’t start writing your book until you’ve answered those questions.

With Dream Teams, I wandered around the intellectual map for a year before I could properly answer these. I wasn’t even sure I was working on a book for long time when I began exploring these concepts.

Initially, I started obsessing over a jumble of ideas that had been tickling my brain for some time. The following things came together in Dream Teams in some form. I found them adrift among a sea of a other ideas I had been noodling on and thinking about writing about as articles, or something:

  1. I’d been thinking a lot about the phenomena that occur when outsiders enter a new field — when physicist Freeman Dyson got into game theory and solved the Prisoner’s Dilemma, or when NASA engineer Lonnie Johnson invented the Super Soaker — and the patterns between that sort of thing and when, say, immigrants move to a new city (resulting in more patents being produced in that city, but also higher reports of fear among residents).
  2. I’d been thinking about how my role in my startup company had gone from “guy who builds things” to “guy who gets other people to build things,” and the paradoxes around creating an inclusive company culture while also wanting outsiders and diversity, for both pragmatic and moral purposes.
  3. I’d been thinking about how breakthrough innovation was often a product of friction, conflict, and rivalry, not sitting around a fire singing songs.
  4. I’d also been thinking about why genius and crazy look so similar, and how we need seemingly crazy people sometimes to help us move forward.
  5. Finally, I’d been mulling over the paradox of how my father (who worked at a nuclear test facility) had taught us kids about how scientists from all these different places worked together to harness this amazing new source of energy… but that same technology was now something those same scientists’ countries threatened to destroy each other with.

Was there a unifying principle to all these things? Was there an umbrella under which some of these fit? I didn’t see it at first. I was exploring all of these separately. Maybe for articles, maybe just to talk about at the bar. I didn’t quite know yet.

After a fair amount of research, I concluded that there was something to the idea of “The Outsider Advantage,” that could potentially make for an interesting book. I started researching and casually bringing up this concept in conversation with friends — just exploring it, prodding it, playing with it.

I eventually decided that the question of “Why is there sometimes an outsider advantage — and sometimes not?” was pretty interesting, and hadn’t been done much justice from a pop-psychology standpoint. The answer to the question soon became obvious: It’s because when different ways of thinking combine, we get creativity and innovation, or chaos and problems. And outsiders bring different ways of thinking with them.

When I started thinking about the ideas around “Different Thinking Combined,” suddenly the stuff I was noodling on about my company’s culture and team dynamics started to make sense in this context. So I started giving people elevator pitches about what I was studying around the idea of “Intellectual Friction” and then more generally, the idea of “The Power of Differences” in the workplace.

After lots more reading and discussing, I realized that learning about the power of differences was interesting — and there was enough new stuff there for a whole book — but the main question that readers would have was, “Why do I need to know this?”

This brought me back to the nuclear energy thing. If we blow ourselves up because we use our differences against each other, that would be a problem. But the inverse of that turned out to be the hook that a book on these kinds of intellectual explorations would need: What if we could learn to harness our different ways of thinking to become incredible together INSTEAD of blowing up? And not just in business, but in society, and at home?

That’s when I realized that we really had something. This was a big, meaty, fascinating topic that science could help us understand better — and a narrative nonfiction book could be the perfect way to talk about it. This was the David in the stone: a book about the art and science of really WORKING together without falling apart.

After settling on the thesis, I went through the following exercise:

The Snowflake Method:

I didn’t invent this; some fiction writer did. But it’s got my name inside it, so I don’t hate if you think of me when you think of it. ;) It’s also been developed separately as “One Sentence, One Paragraph, One Page” in Ryan Holiday’s Perennial Seller, an awesome book on making creative work that lasts.

The Snowflake Method is about starting small and building out your book via a series of increasingly complex outlines. You start with a tiny snowflake, then you make it a little bigger. Then a little bigger. Until you have a snowball. Then whatever is bigger than a snowball.

This method is useful because it helps you clarify your pitch, and gives you a lodestone toward which you can orient everything you write.

Here’s the method:

Step 1: Workshop a one-line description of your book pitch

E.g. how the New York Times bestseller list would describe the book.

This should take longer than you think. I workshopped dozens before arriving at my final one for this book:

How some groups of people become incredible together, and why most don’t.

Step 2: Turn that into a one-paragraph description of your book

E.g. how you might describe your book in 15 seconds to Anderson Cooper

Here’s what I ended up with:

Dream Teams is about a paradox. When groups of humans come together, they can become more than the sum of their parts and make incredible breakthroughs together, but usually our groups slow down or break down instead. Dream Teams is an intellectual adventure through fascinating old history and compelling new science to discover what makes the difference between those two outcomes.

Step 3: Turn that into a one-page description of your book

E.g. what would go on the book flaps?

Here’s one of the final versions of mine:

WHY DO SO MANY PARTNERSHIPS AND GROUPS BREAK DOWN — AND WHY DO A SELECT FEW BREAK THROUGH SPECTACULARLY?

We all know that the best teams are more than the sum of their parts, but collaboration so often fails to fulfill this promise. Studies and statistics reveal unambiguously that individuals consistently outperform teams.

But there are a small number of teams that defy the odds. This book is about those dream teams: the creative agencies, rap groups, social movements, and ragtag armies that manage to pull off amazing things together, far beyond what any individual could do.

Shane Snow takes us on an adventure through history, neuroscience, psychology, and business to reveal what separates groups that simply manage to get by from those that get better together.

Drawing on exciting stories from history, Snow explains how to leverage team members’ diverse perspectives and experiences. He reveals why most mergers flop — and the one factor that predicts failed mergers, marriages, and partnerships. He teaches partners and groups how to fight with one another productively. And he dissects great social movements throughout history to decode the science of becoming open-minded.

Note: this is a little different than what actually ended up on the flap copy of the book. The final includes specific examples that I wrote about for each of the principles. But when you’re just outlining, you probably won’t have these specifics yet.

Step 4: Repeat steps 1–3 for every individual chapter of the book.

In order to do this, you’ll likely need to do more research than you’ve done at this point. So that’s what we’ll dive into next.

III. Research & Reporting

In middle school, one of the few things I liked more than the math club was the Science Fair. If you ever did Science Fair, you may remember the Scientific Method, as taught to school kids. This is basically what I think all writers should keep in mind when embarking on research for their books.

Step 1: Make an observation
Step 2: Form a question
Step 3: Form a hypothesis
Step 4: Experiment/research/interview/etc. to disprove or prove the hypothesis
Step 5: Analyze the results and draw a conclusion

When I go through this process, I’ll typically create an Evernote notebook on the subject, and then I will fill it with notes.

I’ll use Evernote’s Web Clipper to download PDFs and web pages and scholarly research on the subject into the notebook.

I’ll watch documentaries or listen to interviews on the subject while taking notes simultaneously in Evernote in the notebook.

I’ll conduct interviews, record them, get them transcribed at Rev.com, and then dump the transcripts and audio files into Evernote.

I’ll fill Evernote notes on the subject with links to Internet articles and my commentary/summary.

And basically, for each topic, I’ll end up with something like these:

Some observations and questions will not be answerable by researching what’s already out there. So you’ll have to either

a) interview people and extract insights from them;
b) find raw data and extract insights from it; or
c) conduct an original study or experiment.

For Dream Teams, I conducted several research studies and experiments, and supplemented existing research with original, primary research by conducting several national surveys using SurveyMonkey, my favorite tool for polling hyper-specific audiences inexpensively.

I then analyzed the data I got (from both my original studies and data I downloaded from Internet databases) using Tableau, my favorite tool for finding stories in data. Here’s a few examples of how I used the scientific method and these tools to do all that:

Example #1: Innovation vs Inclusion

In the course of research, I came across a statistic from Gallup that said that workers were more likely to do poorly if their managers ignored them than if their managers mainly focused on their weaknesses. I found this curious, and dug a pretty deep rabbit hole to learn about the damaging effects that exclusion, organizational silence, and superficial communication have on relationships — at work or in life in general.

My observation: Excluding people makes for unstable relationships.

My question: How does exclusion affect companies?

My hypothesis: Excluding people decreases the likelihood of producing breakthrough innovations or novel solutions to problems inside of a company.

My experiment: I decided to do a SurveyMonkey poll of American workers at fast-growing, innovative companies, and pit them against workers at slow-growing, non-innovative companies. SurveyMonkey makes it easy to generate lots of data really quickly. So I designed a survey and collected data on this front.

My analysis: I exported the SurveyMonkey data to CSV, and then loaded the survey responses into Tableau. Tableau immediately spat out this chart for me (which we then re-formatted for the book):

My conclusion: My hypothesis was correct. Even more so than I imagined. The results, as shown here, are stark: The more you let someone be themselves at work, the more you allow them to participate from their different points of view, the more likely the company will be fast-growing and innovative.

Example #2: Gay Television

Another big, interesting thread I chased in Dream Teams had to do with the struggle for acceptance of gay rights, and how that related to the stories being told in popular media.

My observation: There seemed to be a lot more sympathetic gay characters on TV these days, and also Gallup polls were showing that people were generally more pro-gay rights.

My question: Which came first: Sympathetic gay characters on TV, or gay rights?

My hypothesis: Knowing what I know about the neuroscience of storytelling, I bet that the stories on television had an impact on gay rights before popular opinion did.

My experiment: I downloaded TV show data from IMDB and made a spreadsheet of all the gay characters on TV from 1970 to the present. In my spreadsheet, I painstakingly indicated whether each character was good or evil (this required a lot of Googling). Once my spreadsheet had all this info in it, I used Tableau to chart the number of gay characters in mainstream fictional television shows per year, as well as the number of good gay characters, etc.

It took me like, three clicks to generate this chart:

I then downloaded a TV script database to chart the usage of gay slurs in TV, and to put the public opinion toward gay people in the 20th and 21st centuries side by side with it and the characters charts. (I got the public opinion data from Gallup.)

All this showed, yep, that gay rights and gay TV were highly correlated:

Further research showed that people in surveys actually credit shows like Glee and Modern Family for helping them change their minds about whether their gay neighbors should be allowed to get married. So I now had quantitative and qualitative research showing that my hypothesis was correct. Hooray!

Example #3: Intellectual Humility

This one was a bit more of an involved observation: Our culture talks about open-mindedness as a virtue, and closed-mindedness as the mark of an un-evolved person. But I discovered that philosophers and psychologists have argued for years about what exactly it means — much less, how to measure it.

I then discovered that in recent years, however, scientists had found consensus around a related virtue that embodies what most people mean when they talk about open-mindedness in everyday life.

That virtue is intellectual humility. It turns out that it’s the missing component in the quest to measure open-mindedness — and it’s something that’s key to making our relationships, partnerships, and governments more excellent.

My observation: Intellectual Humility is super important to being a good collaborator.

My question: How do we develop Intellectual Humility, so we can get better?

My hypothesis: Watching news, reading books, traveling, living places, changing your religion or political views — these kinds of things have long been suspected to help us become more open minded. I theorized that was probably true.

My experiment: Nobody had really done a big study using new research that shows how to measure IH, and asked about things like your media habits or where you’d lived. So I conducted such a study on SurveyMonkey:

My analysis: I ended up with a giant spreadsheet of answers, which I analyzed using, big surprise, Tableau.

Some super interesting things came out of this study in particular. This chart here is where I looked at data on how much time people have spent living in countries other than where they grew up, and how this relates to different dimensions of open-mindedness, their political leanings, and other attributes:

Turns out that traveling to lots of countries is correlated with higher open-mindedness scores. But living in other countries helps even more. So does watching lots of fictional television or reading lots of books! But I was wrong about one thing: taking in lots of news does not increase IH. In fact, even taking in a diversity of news channels (watching both FOX and MSNBC, for example) doesn’t lead to more IH. According to the data, the IH increase only happens with fiction!

I can’t emphasize enough how important it is to do the research and thinking part to death before composing the book. This saves tons of time in the writing process, and it also gives you lots of material to talk about later—stuff that doesn’t make it in the book that you can use in interviews and articles that doesn’t give away the book itself.

Anyway, once the research is done, it’s time to put this thing together.

IV. Outlining (Before Writing!)

You have the research. You have the conclusions. Now you need to weave what you’ve found into a narrative arc that makes sense and helps readers understand what you now understand better than anyone.

Your first instinct for your chapter outlines will probably not be what you should end up with. Every chapter of Dream Teams went through a half dozen different outlines. Here’s how I went about outlining:

I diagramed out the overall concept map for everything I decided probably needed to go in the book. I find that it’s helpful to do this visually, eg.:

This is probably the least awesome way to describe my book. It’s sort of this stale awful way of putting it, but it was useful for my process to put it down like this.

I eventually simplified the diagram to something prettier, a higher-level abstraction of the concepts that I was really writing about (and this one was the most helpful for the organization of the chapters):

Next, I sat down with a Sharpie, my Evernote summary/notes for the topic at hand, and a pack of sticky notes. I used different colored sticky notes for

a) concepts;
b) supporting evidence; and
c) stories that are good examples of these

And then I put them up in different combinations on every window, mirror, or wall I encountered, moving them around and re-considering them until I had an outline that looked like it would work:

Next, I did the Snowflake Method for each Chapter. E.g.:

Ch. 2 One-liner: Teams that break down avoid conflict. Breakthrough teams fight, but they do it the right way.

Ch.3 One-paragraph: Groups of people that have all the ingredients for high-potential collaboration often fail, not because they have conflict, but because they avoid conflict. In this chapter, I explore — through the stories of DaimlerChrylser and the Wu-Tang Clan — how a psychological concept called Cognitive Friction makes the difference between teams that break down and those that break through.

You get the idea.

Finding and telling the perfect stories

Once the snowflake is built, then it’s time for the fun part. Crafting the narrative that gets the reader to care about all this stuff you want them to learn.

I co-wrote a whole book on how to tell great stories. So I won’t rehash all the mechanics of storytelling here. But I will briefly summarize my book storytelling process here:

I get asked rather frequently how I find the stories I end up putting in my books to illustrate the research and principles I want to get across. So I’ll touch on that for a moment here.

I generally look for stories in two categories:

1) Stories you don’t know about people you do know; and
2) Stories about people you don’t know, but you’ll wish you knew them afterward.

So, my story-finding process generally goes along two tracks:

Sometimes I’ll have a principle that I’ve researched and I just need a great story to help people remember it. In that case, I tend to search for less-known stories about people who are pretty famous. If the research is valid, then finding a story to illustrate it shouldn’t be too hard once you know what to look for.

I liken this to when I was a teenager and started skateboarding; suddenly every piece of concrete looked like a skate park. To be honest, I usually start reading Wikipedia summaries about tons and tons of people who I suspect might be interesting examples. When anything piques my interest at the Wikipedia level, I’ll tend to buy a couple of the best biographies out there on the subject and read them, looking for that skate park. (This is how the Malcolm X chapter of Dream Teams came about — after I searched for examples of well-known people who’d changed their minds in epic ways.)

The other way I find stories is through interviews with real, live people. Whenever I’m interviewing professors or researchers or experts of some sort about the research I’m exploring, I tend to ask them at the end of the interview for people who are examples of what we’re talking about. Then I go interview those people and ask the same question until I find a story that really grabs me.

For instance, in Dream Teams I have a chapter on women detectives. For it, I interviewed criminal justice professors whose work I found on Google Scholar, etc., and asked them to put me in touch with badass women detectives, agents, and officers who could talk to me about the principles we’d just discussed in our interview. I took these referrals and interviewed a whole bunch of amazing ladies. One of those ended up being a woman who happened to be the #1 marksperson in the FBI. And she happened to have an amazing story of thwarting a mafia boss in the 1970s early in her career (and soon after they started letting women become FBI agents). She’s not a household name, but when you read her story in the book, I guarantee you’ll want to hang out with her.

Here’s my process for coming up with story structures themselves:

a) Watch J.J. Abrams movies or episodes of TV;
b) Write down the plot structure of each story as I watch it;
c) Sketch out my own stories using various J.J. structures; and
d) See which works best, and modify to fit the way my story needs to be told.

E.g. Many J.J. episodes of Alias go like this:

Start in the middle of the most intense part of the story;
End on an unresolved cliffhanger;
Go back in time and see how we got here;
Get back to the cliffhanger, only to realize it’s not what it seemed.

Or

Start with one storyline, end on a cliffhanger;
Start a second storyline, end on a cliffhanger;
Present a third storyline, which it turns out explains the previous story;
Wrap up the second story, using knowledge we just got from the third story;
Surprise! Wrap up the first story using knowledge from the ending of the second story!

Etc.

I do this kind of story structure analysis with any article or movie or TV show that really gets me going. I’ll save my dorky little outline for later, and then bust it out when I have my own story to tell. You’d be amazed how a story about a boring corporate merger can get exciting if you tell it like J.J. Abrams, and weave it in with the story of a rap group almost killing each other in a recording studio.

Nowadays when I write, the stories come last. Whereas I love the stories the most, the research and thinking needs to come first. There will always be stories to put meat on the research bones. When I used to write story-first, I would tend to run into a problem: I wouldn’t want to cut the story because I loved it so much — even when that story ended up being a not so great example of the principle, or worse, when it ended up being an exception rather than a proper example.

Check out this video where I talk more about my writing and research processes.

V. Titling And Positioning

This is the point where I think authors should start seriously thinking about the way they will position their book for maximum sales and marketing appeal. You have the ideas, the research, the concepts. Now you need to figure out what the final package is going to say to people.

Ryan Holiday, whose been a guiding force for my book writing and marketing for years, advises in his wonderful book, Perennial Seller: The Art of Making and Marketing Work that Lasts, that book marketing starts with the manuscript itself. You want to work the book’s pitch into the content itself from the beginning.

My theory on book marketing can be summed up by this chart I made here:

The title and subtitle matter a great deal for Conversion Rate, which is how many people out of 100 will buy the book when they see it.

(My favorite recent example of the power of this is an author buddy of mine who wrote the book The Subtle Art of Not Giving A F*ck, which has sold millions of copies. He says he originally wanted to title the book, Negative Self Help. Glad he didn’t stick with that. That book would have sold about 3 copies.)

The book title was particularly difficult for me this time around. I ended up making giant spreadsheets of potential titles and bothering friends and acquaintances for their opinions on them for MONTHS. The problem was I hadn’t fully fleshed out my outline and organizational concepts when I started working on titles. Basically, I knew that getting the positioning right was important to do early on, but I started too early.

Here’s a screenshot of one of my awful title spreadsheets:

For the record, I KNOW most of these are BAD. But I show you this to illustrate how important it is to really work on getting the title right.

For a long time, I decided I wanted the title to be The Plus Ultra, based on an apocryphal story of a ragtag group of geniuses at the turn of the 20th century banding together to solve world problems. I even mocked it up to see how people liked it.

Ryan Holiday told me that people would either decide I’m a genius for that title, or nobody would ever pick it up, so it would never get enough exposure for people to realize how cool it was. Ryan suggested, “Why not call it Dream Teams?” since I had used the phrase in my snowflake outlines.

Yep. That was the one. Blast that handsome man.

The subtitle was more straightforward. After lots of back and forth on different formulations around the idea of breaking through instead of breaking down, one day my editor, Merry, who is the fricking best, suggested, “Working Together Without Falling Apart,” and there we had that one too.

In other words, I can’t say there’s a science to book titles. More of an art. But don’t settle until you have something that lights people up immediately.

VI. Writing and shaping the book

Everybody’s writing process is different. (I interview an author every month on my blog to get theirs!) But I subscribe what I call The Michael Lewis Method:

1) Research and outline in extreme detail;
2) Go over your notes until you basically know them by heart; and then
3) Hole up and write it all as fast as you can.

For Dream Teams, I primarily went to South America. For a little over two months, I would write for 14 hours a day from Monday to Friday, travel to a new city on Saturday, rest and explore on Sunday, then repeat.

At this point it was just about typing, not about thinking. So my goal was to put myself in a scenario where I could do as much of it as I could. Here’s what I do when I’m cranking on this kind of writing:

  • Go somewhere where nobody knows me
  • Shut off notifications on my phone
  • Every morning follow the same routine: Wake up, meditate, and exercise — so my brain and body are ready to go — then…
  • Go to a coffee shop, drink coffee, and write
  • Go to the next coffee shop whenever I started getting distracted or antsy
  • Repeat until dark
  • Wind down / reward myself at the end of the day with an episode of something totally unrelated to the book (this time for me it was mostly The Expanse)

Note: If you do this long enough, you WILL go crazy. That’s why moving locations each week helped me. But if you know exactly what you’re going to write down, you won’t need that long to do this.

Also note: Some people just can’t sit down and work for 14 hours a day. I think that’s why all my writer heroes did speed. I find that I can pretty much do this with just coffee.

My actual chapter assembly process is as follows:

  • Pull up the outline, put it into a Google Doc
  • Pull up the research in Evernote and open up all the links to reference materials I’ll be quoting or referring to (clipping any PDFs down that I haven’t yet saved from the web into my local notes)
  • Copy/paste research snippets and notes into the proper spots of the outline
  • Overwrite them all with my own narrative
  • When I’m finished, copy/paste the chapter and put it into Hemingway
  • Try to take out as many “very hard” sentences as you can (Hemingway highlights them in red), and decide which adverbs and “hard” sentences to remove/fix. My goal: reduce the reading level to 7th or 8th grade.
  • Copy/paste back into the Google Doc, format back to normal
  • Add graphics and figures as necessary
  • Send it to my editor and watch an episode of The Expanse

Want to see this in action? I took a screencast of me writing the first draft of Chapter 4 of Dream Teams:

Assembling Chapter 4.0.1 of Dream Teams, fast forwarded to 1 minute

VII. Editing, Finessing, and Bulletproofing

To keep track of everything, I used a number system for my chapter drafts that’s much like a software versioning system. Every chapter was titled like this:

[DT] 1.0.1
[DT] ← for Dream Teams, with brackets so it would come up first alphabetically in Google Docs for easy retrieval
1.0.1 ← Chapter, major draft, version of the draft

Every day when I started work on a chapter, I would save a copy of the previous draft as a new version (1.0.2 now), and then start writing. Whenever I was ready to submit the chapter for people to review, I would save it as a major draft (e.g. 1.1.0).

But editing is not a solo process, of course. So every time I had a major draft, I would loop people in to help tear it apart and build it up again. I made everyone use “Suggestion Mode” so I could decide what to keep and what to cut, and to make sure that changes people made didn’t end up sounding like someone who wasn’t me.

One of the best pieces of advice about the book process is something my agent has said more than once to me:

He advised me to think of myself as the CEO of the book. Everyone else who’s helping, he said, are kind of like my “employees” (even if the book publisher thinks of it the other way around).

In other words, it’s your book, your name is on it, and you care personally about the outcome more than any other individual. So you need to manage the process, rather than be managed by it.

That said, it’s not going to be a good book if youdon’t let these other people push you to make it better. So your job as the author is to collect feedback and edits and take them seriously. You don’t have to accept every idea that someone has, and you can push back on your editor (which I did, a lot — thanks for being a good sport, Merry!), but if you are not open to changing every word of your book, it’s not going to be a great book in the end.

Here’s the squad of the different people who helped me tackle different parts of the editing and refining process of the book. I would send each chapter to these people, in the following order, for their edits/suggestions. I’d then revise, deciding which things to keep and which to not, before sending it to the next person in this chain:

  • Jim, my agent, for general notes; then
  • Frank, my hilarious lawyer/novelist buddy in Bermuda (for line edits and making it funner); then
  • Merry, my Penguin editor, for big edits and line edits; then eventually
  • Cara, my fact checker, for smaller edits and to verify accuracy of every little tiny detail; and then
  • My four sensitivity readers, to catch little things that might distract or offend people for no good reason; and finally
  • Random other friends, to tell me when they got bored, so I could make those parts better (or remove them).

For the sensitivity readers and other friends who were just reading and not editing, I actually used Contently Docalytics to host the manuscript pages. This way I could track what pages people spent the most and least time on, and where people dropped off, so I could shore up the complicated parts that people didn’t speed through, and fix the parts where people clearly got bored:

Perhaps the best advice I got besides Jim’s, when it comes to editing, came from an author friend of mine who told me to just let people read your drafts and mark the parts they got bored.

Don’t ask them for suggestions for what to do about it. Just have them identify the problems. I like this advice very much, because as the CEO of the book I know more about what’s going on than most of my collaborators. So suggestions will tend to be less-informed. Sometimes they’ll be helpful, and sometimes they’ll be distracting or off-base. But anytime someone tells you they’re bored, that’s going to be useful feedback.

And here’s where I’ll reiterate a previous warning that bears repeating: Be prepared for LOTS of editing and revising. I spent 3x as much time revising as I did writing. If you do less than that, you’re either a prodigy or you’re leaving potential on the table.

VIII. The one book cover tip you’ll ever really need

People judge books by their covers. Sorry. The cliche that says otherwise is advice, not what people actually do. (Remember my diagram above? The conversion rate of how many people buy your book depends enormously on whether the title gets them or not.)

Thus, I am really feisty about my book covers. My first goal is for the cover to stand out in the sea of other books out there. My second goal is for it to not make me look weird, since my book cover will follow me around for the rest of my life.

For that first goal, I found the most useful exercise to be to take the book cover mockups my publisher sends me, and photoshop them onto Amazon search results pages to see how much it stands out:

Notice there is not one, but four Dream Teams covers in this. A couple of them are okay, but Dream Teams isn’t the book that stands out here even though there‘s more than one. Fun fact: the book that stands out the most to me in this screenshot—Originals by Adam Grant—well, we ended up getting the designer of that cover to design the final Dream Teams cover.

That’s basically the advice here. Keep running cover ideas through this gauntlet until you find something that actually catches people’s attention.

That’s how we got this, which I’m super proud of:

IX. My Book Writing Toolkit

Here’s the list of tools I used to make Dream Teams. I explained how I used them earlier, but just for summary:

  • For note taking and organizing all the research: Evernote. This is the best tool I have found for projects that involve research, writing, and collaboration. I’ll explain more later. But if you’re a writer and you’re not using Evernote, I hope you are some eccentric who only writes on a typewriter in a bathtub. Because if you’re not, you’re doing yourself a disservice on this one.
  • For interviews: I use Automatic Call Recorder Pro for Android (there ought to be equivalents on iPhone, or use Skype) for my recorded interviews. Then I get the interviews automatically transcribed into a Word doc via Rev.com. Rev is the freaking best, you guys. Temi is good too in a pinch if you don’t need super accuracy.
  • For word processing: I wish I could use Evernote for this, but editors always want you to use Word because they’re used to the layout and in-line commenting / track changes features. I managed to get everyone on board with Google Docs this time around, which has all that but is just an easier user experience and is all in the cloud.
  • For files, assets, sharing, and backups of everything, I used Dropbox, with separate folders for the manuscript, graphics, marketing, cover, etc. You will end up with a lot of files, trust me, so set this up from the beginning. (From this shot it’s clear that I definitely organize my book files better than my other files lol.)
  • For charts and finding stories in data: Tableau is the absolute best. I used Tableau for the original studies I conducted, and to parse out patterns in huge data sets I downloaded.
  • For making the writing flow better: HemingwayApp, based on what I learned in writing this old post.
  • Analog tools: I am a big fan of making giant sticky note maps on walls and windows. If I’m taking notes by hand, the only tool that will do for me is a Blackwing 602 (Steinbeck’s pencil of choice!) on a Moleskine notebook:

I love Blackwings so much I actually have one tattooed on my inner arm:

X. Final Thoughts

It’s a surreal feeling the first time you hold your own book in your hands. But making the book is only half of the battle. Maybe even less than half of it. Launching the book, marketing the book, and keeping the party going — that’s hard work. I’ll be writing another post soon about all that.

I’ll close by saying this: you’ve surely noticed from reading this post, writing a book is not a solo process. Even though most of the time will be spent alone, a book requires lots of collaboration. Lean into that. Include people in your process. Invite their critiques. Bounce your ideas and arguments off of everyone you can. Workshop the book together.

Do that and, dare I say it, you might just realize that your book was built by your own little Dream Team.

See you out there.

–Shane

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