“What is going on?”

My head tilted to the side, mouth wide as if to emphasize my inability to explain.

“I don’t know. No one’s articulated it, you just gotta show up.”

I was eating an omelet and drinking coffee at 8am Wednesday October 22nd at the A2 cafe in Bangkok.

“Yeah, you do.”

“When people understand this, it’s going to change everything.”

“Yep.”

We nodded and turned back to breakfast. We’d had this conversation before. It never went anywhere.

We were at a business conference in October of last year where three hundred entrepreneurs from around the world had met in Bangkok to talk about was going on in their businesses and in the community.

I remember the date because it was the day I dived down a rabbit hole that has consumed most of my creative energy since.

I started writing a book to explain “what was going on.”

My plan was to hole up in Saigon, Vietnam for two months before Christmas and bang out a book. That was overly optimistic, to say the least. I got a first draft done but massively underestimated the time and energy required (more on that later).

I didn’t really understand what was required for how to start writing a nonfiction book. Since I’ve talked with so many people considering it, hope this article and those that follow will give you an idea of what’s required, what it looks like, and hopefully save you some time and energy by learning from my mistakes.

Why Write a Book?

Before going into the process of writing, make sure you know why you’re doing it. Flagging motivation has killed more creative projects than the Medieval Popes. As with any substantial creative undertaking, you can safely assume it will take you twice as long and be twice as hard as you expect.

For me, there were three reasons:

1. On a personal level, it’s something I’ve always wanted to do. No other medium has impacted me like books have and it’s inspiring to work to be a part of that.
2. Magic is happening right now for (prospective) authors. Self-publishing has democratized the publishing, making it much easier to publish (not write!) a book.
3. Brand definition – As I’ve “turned Pro” over the last year and especially in the last few months, I want a robust piece that defines the brand going forward.

So, What is Going On?

As I reached graduation and the end of school, I confronted the life I had been imagining for the prior four years: law school.

When I fully considered it, the idea of not being able to travel, to work on things I found meaningful, and to own my time was deeply unsatisfying.

And so I started trying to figure out what else to do.

I worked at a local marketing agency using a small kitchen furniture publishing business I’d built on the side.

I went from intern to lead project manager, managing accounts for international manufacturing brands and higher education institutions.

I left to go work with a publishing business, where I edited a top 25 iTunes podcast and 10,000 subscriber blog. I planned events and managed a private organization of over 1000 location-independent entrepreneurs.

I managed the online marketing for a portfolio of eCommerce businesses in the hospitality industry.

I spent six months running sales and product development for a valet parking software startup, selling into enterprise parking operators while managing product development and strategy as well as an overseas team of developers.

I spent three years working with entrepreneurs. What was so special about them that I hadn’t understood before?

Turns out, not that much.

Yeah, they’re smart; they’re trying to do something interesting and meaningful with their lives. But that’s true of a lot of people.

What was the difference?

There’s a lot of people that try to “sell the dream” of entrepreneurship.

“Do what you love!” “Follow your Passion!”

They make it seem like it’s all rainbows and fairytales, all upside and no downside.

That argument never really appealed to me.

For one, it felt disingenuous and fake. I can hear the soft, mounting wails of the bullsh*t siren winding up in the back of my head everytime I hear it.

For another, I never hated any of the jobs I had. I just found them less satisfying and exciting than I felt was possible, and I figured if I only had one life to live, I might as well do it right.

I also haven’t talked to a lot of entrepreneurs that would describe their experience or lives as “easy.”

Psychologically challenging, emotionally testing, and physically exhausting? Frequently.

Worth it? Almost universally.

So, what is the difference?

Most entrepreneurs I know run businesses that could not have existed a decade ago or, in many cases, even five years ago. They’ve taken advantage of structural changes in the global economy, mainly globalization and the internet, and updates to social scripts that have happened in the last decade.

The social and technological inventions of the past one hundred years have carried us to a point where jobs no longer create meaning, freedom, and wealth in our lives. We’ve hit peak jobs.

Those same technological and social inventions have made it easier, safer and more profitable than ever to become an entrepreneur, to harness our innate human drive for money, meaning, and freedom to make a dent in our lives, the lives of those we love and the world at large.

I believe that if a lot of people on the fringe—who may have friends doing entrepreneurial things or have read about it—understand what’s going on, they’ll choose it not as a way to “escape the cubicle,” but as a strategic life decision that aligns with their values.

Much of the language used now to describe paths like law school, medical school, accounting, and other “good” jobs is dated. If someone is considering investing the next forty years of their life in it, it’s worth asking how “safe” or “smart” those paths are and will be for the next four decades.

I’ll go into more detail about the book over the next few months.

If you’d like to be on the updates list and get a free early copy, drop your email here.

The rest of this article will be more about the process of writing a book in 2015 for anyone else interested in doing the same thing.

I’m going to go pretty specific and deep into my writing process, which may or may not be applicable to you depending on your industry, writings style, and goals, but I prefer specific—if not perfectly relevant—examples than broad platitudes.

How To Start Writing A Nonfiction Book

Daily Writing Process

• Open up Scrivener
• Turn on Freedom
• Turn on tunes (Currently Jungly – Busy Earnin’ on repeat)
• Read over Target Reader and Promise of the book
• Review writing prompt from yesterday
• Start writing on prompt from yesterday
• If you’re stuck, start journaling
• If you aren’t excited about it, either get excited or write something else. If you aren’t excited, the reader won’t be either.
• If you can’t get clear ideas, review notes of books that inspire you.
• If writing starts getting too philosophical/abstract, imagine emailing it to a target reader
• When finished, log progress into Writing Tracking Spreadsheet.

My goal for everyday is 2k words. If I get on a roll and go over that, I keep rolling.

I don’t always hit the goal either, especially on heavy editing days. I’m not sure word count is the best measure of productivity as I enter the middle stages of writing the book. Frequently it’s the days I delete more than I add that actually improve the book.

On a day-to-day basis, writing output for me seems to follow the same pattern as advertising spending. I need the first thirty minutes or so to review and load up my mental RAM for the book, then I usually get two to four hours of high quality output before I hit brain drain.

Anecdotally, this is what a lot of other authors and writers have shared with me as well. Initially, I tried “not being a pussy” and pushing through but this actually created more work since everything I wrote after the three to five hour mark not only took time to write but then took time to delete or edit the day after.

Tracking

I use a Google spreadsheet that I fill out at the end of my writing sessions every day with some basic data points, notes on that day, and a prompt for the next day.

The bottom row show my average output over the course of a month on days that I wrote.

I track the words using Scrivener. If you go to Project → Show Project Targets, you can set up a daily project target based on your deadline.

I.e., If you want to write a 40k word book in 60 days, it will auto-calculate how many words you need to write that day to get on pace. This is HUGELY motivating for me, as it provides a little red/yellow/green status bar that incites me to just keep pumping out words even if I feel stuck.

My word count/hour seems to be way under average, but I’m lumping editing into writing time so on big editing days I’m usually at 0 new words output.

There also seems to be a distinction between writing what you know and writing to know .

I.e., Sometimes I’m writing something that I’ve already got composed in my head and just need to get on paper, and sometimes I’m writing something that I still need to figure out and the writing is the process of figuring it out. Word count while writing the later is far higher unsurprisingly.

Draft and Book Writing Process

The structure behind my writing process is mostly stolen from an interview with Neil Strauss on his writing process by Tim Ferriss. I’ve added specific mindsets, prompts, and thoughts that deal with exactly how I personally write.

I developed this writing blog articles and have found it to be equally useful for how to start writing a nonfiction book.

Draft 1 – Thinker/For Myself

The goal of the first draft is to get the logic of the piece to make sense to me when I read it all the way through; tone is conversational, like an informal email.

• Imagine emailing this to a target reader
• Are you excited? Is the writing emotionally compelling?
• If there is a way to graphically display the thinking? Can you add a graphic?
• Figure out the angle of the sections as soon as possible and build it around a specific example of a big idea. One Idea Per Section!

Draft 2 – Writer/For The Reader

The purpose of the second edit is so the reader understands the concepts more clearly. The writing should support the thinking in the sense that it doesn’t force the reader to think about the writing, and instead lets them focus on the thinking.

• Create an overarching narrative – Add stories, analogies, and metaphors; try to paint pictures to make it easier to understand
  • Start in the Middle – Add a hook/anecdote to start the post. Michael Lewis is exceptional  at this.
    • If feasible, loop back to this throughout the post to create an overarching narrative throughout the post
  • Make sure each logical point has a clear illustration if not self-evident.
• Address Questions/Common mistakes
  • Is there a smoother way to say this?
  • Bridge points together with smoother transitions
  • Did you remove conversational transitions (ex. so, say, like, sort of)?
  • Are you preaching? Don’t preach.
  • Remove “it”or “that” or “this” and use actual examples or synonyms
  • Make it as short as possible. Did you remove every unnecessary word? Get rid of all instances of the verb “to be,” “very,” “really,” and “a lot”
  • Don’t use obtuse language (like “obtuse”); speak simply and clearly – like Lincoln would
  • Is there any section you skim? Delete it or improve it. If you don’t want to read it, no one else will either

Draft 3 – Marketer/For the Haters

The purpose of draft three is to pre-handle any potential objections and think about how the piece will be received. How can I bake the marketing into the piece?

• Optimize for impact –
  • Heading should create intrigue and state the benefit immediately. Write 5 different options for each subhead and 10 different options for each heading. Use Contradictions and Open Hooks, such as: “How a Coke Bottle Can Ruin Your Life.”
  • Pre-handle any potential objections from haters.
  • Rewrite the introduction/hook. Is the first paragraph emotionally compelling?
  • Rewrite the Conclusion. What will the reader leave with?
• Don’t “sell the dream” – Be assertive and bold in the body, use a small section at the end for haters if you must, don’t qualify throughout
• Don’t name drop by calling people “my friend” (personal bad habit!)
• Re-address questions/common mistakes
  • Is there a smoother way to say this?
  • Bridge points together with smoother transitions
  • Make it as short as possible; remove every unnecessary word. Get rid of all instances of the verb “to be,” “very,” “really,” and “a lot”
• Think about how people mentioned will receive it: how can you tie them into the marketing?

General Frameworks for Writing

• Optimize for impact, not shares. Better to deeply impact a few than shallowly impact a lot, i.e., Be the Atlantic, not the Huffington Post
• Explore concepts which you don’t understand and use writing to define them.
  • “The test of utility I propose is whether we cause people who read what we’ve written to do anything differently afterward. Knowing we have to give definite (if implicit) advice will keep us from straying beyond the resolution of the words we’re using.” – Paul Graham

Major Lessons Learned To Date

On First Steps

Define exactly who you’re writing the book for. Where do they live? What do they do? Are they single? married? Intelligent? Ambitious? How old are they? Write down exactly who it is (better if you know them) and think about what a day in their life would look like.

Don’t start writing until you have an outline. This may take a month. Yes, a month. It depends on your writing style, but put together an outline and send it to 5 people that you would want to read the book and see what they say. If it’s not compelling to them, you just saved yourself a lot of work. I’ve thrown out around around 40k words already. That’s a lot of wasted time that a good outline could have solved.

The Promise is the Linchpin – What’s the promise of the book? “After you read this book, X transformation will happen in your life.” What’s X? Keep both the promise and the person you’re writing the book for in a note and read it every time before you start writing. Everything in the book is for that person, to achieve that result.

If I were to start again today, the first thing I would do is create a document consisting of who the book is for, a rough outline, and the promise of the book, and show that to 5 people I wanted to read the book and keep tweaking it until they were excited to read it. That being said, if you’ve never written a book before, I’m not sure how possible this is. I had to write 20-30k words before I even figured out what the books was about, so if you can’t figure out a promise and outline, just start writing and see what comes out.

On Process

Momentum/One Thing/Consistency – A book is greater than the sum of it’s parts. One of the mistakes I made, and that I suspect a lot of other bloggers make, is that it seems as if a book is like writing a lot of blog posts. If a book is at least 40k words and I usually write a 2k word blog post, then it should take me twenty blog posts’ worth of time, right?

Nope!

It’s difficult to “keep the book in your head” if you only do it intermittently. If I take more than a day off from the book, the first day back is usually just catching up and loading up the mental RAM to put it back in my head. If you can schedule 1-2 hours everyday to “go to the writing gym” ON THE BOOK (writing blog posts hurt my book momentum) and be consistent, your time will be spent a lot more efficiently.

Writing style and objective matter a LOT – The point above is relative. Dan Norris wrote most of The 7 Day Startup in a week. I’m two months in, and still have a lot of work to do. This is in part because Dan appears to be a content machine, but it’s also in part the nature of the book. If the book is primarily prescriptive and you already know the prescription, I suspect it’s a lot easier to write.

Ash Maurya hacked this process by teaching classes first, then writing the book based on the feedback from the class. If the book is more of an exploration than a prescription, this is more difficult.

If you aren’t excited about it, don’t write it – If what you’re writing doesn’t get you noticeably emotionally aroused, it’s not going to be very good. Either you need to take some time off and recharge, or pick another topic.

Book writing is the most creatively draining activity I’ve ever done – I thought I’d done creatively draining work before, but a book has proved to be totally different. Five hours of book writing broken up into two writing sessions (Usually 3-4 hours in the morning and 1-2 at night on a good day) leaves me in a state where I can barely think enough to tie my shoes.

On length – I’m currently at around forty-five thousand words. Based on other people I’ve spoken with, 180-200 pages (roughly 45-50k words) seems to be the bottom limit for a “book book” in most people’s minds. I don’t have a clear end word count at this point. I’m more focused on making it good than a certain word count, so anything in the 45k and up range would be fine. You can tell when you read a book and the author threw 20k words of fluff in, and I don’t particularly want to be that guy.

Deadlines and deliverables are sacred and to be treated as such – Set Deadlines and Deliverables, and then break them down into daily writing chunks. For example: One month to finish Section One means I need to finish Part 1 of Section One, which means today I need to write 2000 words on why we’re over-credentialized. I plan this out at the beginning of each week in Evernote:

On Alpha Readers

I sent the first draft of the book out to two people that I would want to read it, as well as two writerly people. This is a good mix. There were a lot things that my target readers liked or didn’t like, but they couldn’t articulate why because they’re not writers themselves. The more writerly reviewers helped with that.

I sent it out in Google Docs since Google Docs now has track changes. I sent everyone their own copy to keep the feedback separate but I’m not sure if that’s really necessary/helpful. My editor pointed out that as a reader, it’s sometimes nice to bounce off other people when generating feedback. But as the writer, you don’t get the emphasis on which parts multiple people had issue with since most people will skip over critique that someone has already noted. It definitely creates more work. I’m still in the process of putting it together, and I’ll update on this once I have a better perspective on it.

Current Timeline

Oct 22nd 2014 – Decide to Write Book and Start Introduction Dec 18th 2014 – Finish First Draft (113 Writing Hours, 44,268 Words, average of 468 Words/Hour)

Current Experiments/Status

Blogging it Out – Certain segments of the book I’ve written about here on blog. Because of the value of momentum, being able to spend 6 days each week on the book instead of just 2-3 is much more productive. If I take 2 days off to write a blog post and then Sunday off to recharge, I usually spend all of Monday just loading the book back in my head. So I really only get two days each week working on it. However, there are a couple of issues with this:

1. 1. The book has to be greater than the sum of its parts – I’m not a huge fan of blogger books that are just repackaged blog posts. If they claim it’s just repackaged blog posts, that’s cool. However, I feel like there has to be a substantial amount of editing done to truly create a book and it can sometimes lead to the “sunk cost fallacy” of figuring out how to force blog posts into a book that really don’t belong there.
   2. Heavy editing has to be done, since a blog post requires a narrative arc (beginning, middle, end) which, when thrown in the middle of a book, is disjointed.

My next round of experimenting is going to be using the blog for concepts on the fringe of the book. In other words, certain ways of explaining a concept or concepts that branch off from the main idea.If it does well on the blog, I can stick it in the book. If it doesn’t, I toss it, but hopefully I still kept the book in my head 6 days of the week, so I eliminate any switching cost.

Rewriting the promise – I’ve spent the entire month writing and rewriting the introduction and promise of the book using this outline

• Problem
• Solution/Benefits
• Assert My Credibility
• Reassert Benefits
• Overcome Objections – Top 10 Questions and Objections and Answers
• Make Promise
• Warn Against Waiting

Getting the promise super clearly defined seems to be the linchpin piece for the book at this point, as it will let me know exactly what the deliverable for the final book looks like and exactly what I need to deliver on.

I’m starting to think of the introduction as a sales letter pre-selling the book like you would with a SaaS app or info product. If I can define exactly what the product is and describe it in a way that’s compelling, then I have my marching orders for writing the book.

Writing Resources

Books on Writing Books

Bird By Bird – Anne Lamot

War of Art – Steven Pressfield

On Writing Well – William Zinsser

On Writing – Stephen King

Writing Tools

Scrivener – This is my first foray into Scrivener. For one, it does feel sort of cool. It’s a lot more writerly than Google Docs. The two essential features are:

1. 1. Outline – Because you can hierarchically structure the book in outline mode, it’s a lot easier to see how everything connects and how to move the pieces around. I usually don’t look at tutorial videos for new software and just jump in, but spending a couple hours understanding Scrivener was a good investment.
   2. Track Progress – This is the most important Scrivener feature for me. You can gamify the whole writing session, which, if you’re trying to pump out a shitty first draft, is essential. Hard to overstate the value here.

Freedom – No Internet is 100% for me when writing. I’ve never had a more well-looked-after inbox and budget since I started writing. I’ll find ANY excuse to avoid writing, so blocking myself off the internet entirely is the only solution. I still have access to Kindle and Evernote offline if there’s anything I need to reference, but generally find it’s best to skip researching if I’m in the flow and come back later. So if I hit a point where I want to know, say, the number of law graduates in the past 5 years, I’ll just make a note and keep writing instead of looking it up.

Coffee – My Drug of Choice.

Google Docs – Seems to be better for shorter content. Scrivener helps me see the outline and move parts around more easily than Google Docs does. If I had to guess, I would say 20kish words is probably the turning point where you need to get out of Google Docs and into Scrivener. I’ll be posting regular updates about my writing process and the phases the books if moving through, so if you’re considering writing a book this year, drop your email in the box below to watch it unfold.

Last Updated on July 30, 2019 by Taylor Pearson