How to Write a Book

I’m going to jump right to the punch line. I’m going to start by telling you exactly what you need to do in order to finally write that book you’ve been promising yourself for the past three years. Are you sitting down? Good.

Don’t write a book. Even better, stop thinking about writing a book. Your endless internal debate and self-conjured guilt about that book you haven’t written yet is a sensational waste of your time. My guess is if you took all the time that you’ve spent considering writing a book and translated that into actual writing time, you’d be a quarter of your way into writing that book you’re not writing.

So, stop. It’s the only sure-fire way to begin.

The Weight of Big Decisions

The theory about big decisions is that they require a tremendous amount of thought, and that investing in all this thought results in better decisions. There are many classes of decisions where there is a right move. Where deliberate planning around complex issues involving different people with varied goals is essential to making a correct decision.

Your unwritten book is not one of these decisions. Stop debating it.

I’m just about done with my book, Being Geek. This is my second book, so having gone through the process once before has given me experience that I am using for planning. There was an arc that I wanted to write about and a table of contents eventually did show up, but, by far, my most productive move regarding writing a book was — wait for it — writing.

A blank page. A scribble in a Moleskine. That tweet that captured your thought better than a chapter ever would. Quietly crossing out paragraphs you loved. These are the acts that comprise writing a book, not talking about it, not announcing that you’re going to do it, and certainly not reading an article by a blogger who at this very moment is procrastinating finishing his own book by writing about how you should start yours.

The Journey is the Book

There are scenarios where you’re going to want to plan the hell out of your book. If you’re writing the definitive medical book on the treatment of West Nile encephalitis, I would like to encourage you to plan the hell out of this book. These are books where the structure and the data are essential to this book’s success.

This is not the book that you are writing. In fact, if you’re a frequent reader of Rands in Repose, I would suggest that even if you have a book in mind, that is not the book you’d end up writing. Having done this twice now, I can confirm that the only part of my planning process that made it to the published work is the title.

It’s not that I ended up with an entirely different book than I intended. I wrote the book I intended to write, but the majority of the writing involved discovering ideas randomly, without planning, and in some of the strangest places. The following is the documentation of tools, strategies, and mind games I use to remove barriers and create a book.

The Title and the Pitch

If you’re going to obsess about something early on, my recommendation is to obsess about your title. Giving clever names to people, places, and things is my schtick — I know when I’ve succinctly and adeptly identified a thing, and once I’ve done it I stick with it. There wasn’t a moment during the writing of either book when either title was debated or at risk.

As for the pitch, well, if your title (“Managing Humans“) has done its job, you don’t need a great pitch. However, the other title (“Being Geek“) doesn’t always define your arc like you’d want, so you need the pitch. “A career handbook for geeks” is the pitch for the second book and it came straight out of early discussions with my editor.

The title and the pitch aren’t just the backbone of your book; they help define the literary space that you’ve chosen to write within. While I think it’s important to define some constraints up front, I’m more interested in your writing, so if you haven’t fallen in love with your title, don’t sweat it. Take your best shot and get back the writing.

Mobility, Pt. 1

Once your brain is engaged with your book, ideas are just going to show up randomly.

I make it a practice to keep a travel-sized notebook and pen with me at all times. When I forget these essential tools and my iPhone is nowhere to be found, I have no qualms about asking a stranger for any type of writing instrument in order to capture the relevant thought on the nearest portable writable surface.

The rule is simple: if you don’t write it down, it never happened.


Haphazard notes are then transcribed into TextEdit.

The entire first draft of both Managing Humans and Being Geek was written in TextEdit. I eagerly test-drive the latest gorgeous, time-saving, writer-specific tool, but after each evaluation, I always return to TextEdit.

Why? Barriers. I’m uncertain if it’s a nerd perspective or a writer one, but once you’ve begun a book, the world transforms into a menacing place intent on distracting you from doing what you love — writing.

See, you’re chasing an elusive high where the story just pours out of your fingers, and it occurs so infrequently that you start to wonder: is there a system? Is there a perfect sequence of events that conjure writing nirvana?

I wrote four effortless pages sitting on that high bar stool in the Los Gatos Coffee Company. And I had a black coffee, a 10% Kona blend… in my favorite mug… on a Tuesday.

What was a random sequence of events becomes your writing religion and suddenly you’re obsessing over the seating arrangements in your local coffee shop rather than doing what you love.

Humans, especially nerds, are creatures of habit. Often, these habits are designed to make the world a predictable place so that our brains can focus on the creative task at hand. The reason I continue to end up in TextEdit is because my favorite feature is the lack of features.

Here’s just a slice of one of the preference dialogs in a great writing tool called WriteRoom:

Do you know what I see? I see hours of gleeful distraction tweaking features and defining the perfect writing environment. In TextEdit, there are no knobs and dials for me to fuss with in order to optimize my writing experience.

Features create choice and choice is a dangerous distraction and the last place you want to find distraction is in the tool you use to write. In TextEdit, I set one preference — body text: Sentinel 15 pt and then I start writing:


I have two writing states when generating new material. A fresh thought and an edited thought. The fresh thought state is when I’m staring at a blank page and starting a new article or chapter. The edited thought state is when I’m firing up an incomplete article and picking up where I let off.

Starting, in both states, is tricky, but it’s trickier picking up the editing state because I’m lacking the original raw motivation that caused me to fire up TextEdit and attack a blank page. My move in acquiring my train of thought is to re-read what I’ve already written and then retype the last two or three paragraphs of the existing work. This is usually enough of an exercise to kick off the mental dust.

My other momentum move involves the [square brackets]. The writing zone is a tenuous one and sometimes the thought just can’t be expressed in words, yet. Rather than getting lost in a single sentence, I put my best effort in [square brackets]:

  • [Something about writing being hard]
  • [You can say this better]
  • [Blah blah blah I can’t be eloquent in a chair where my feet touch the floor].

[Square brackets] get those niggling thoughts out of your head and onto the paper so you can focus on moving forward.

Mobility, Pt. 2

Given that you can’t predict your writing mood, you need to have the entirety of your book at your fingers regardless of where you are on planet Earth. Better yet, I’d prefer if you had every single version of your chapters at your disposal.

This used to be a daunting requirement before Dropbox. Not only can you now have every single word you’ve written available on any computer on seemingly any platform, you also have access to every saved version as well.

As I’ve written before, the magic of Dropbox is that once you’ve started dumping chapters into your folder, you simply forget about it. You forget that your writing is seamlessly copied to all of your computers. You forget about that chapter you had to rewrite after accidentally deleting it from your USB thumb drive. Once again, you have a tool that eliminates distracting barriers.

Chapter Evolution

You must become comfortable with incompleteness. At one point during the latest book, I had seven chapters in various state of doneness. When I began Managing Humans, I’d get panicky if I didn’t complete one chapter before starting the next. This is your brain, once again, trying to organize where it shouldn’t.

The reason I have simple, readily available tools is that I can never tell when I’m going to be able to write. I’m on a deadline and my editor is breathing down my neck, which means I do have a weekly writing schedule that carves off mornings three days a week. As I settle into one of these mornings, it’s just as likely that I’ll write as it is that I’ll count the number of folks in the room who’ve chosen to drink from ceramic mugs versus paper cups.

A singular focus on finishing a chapter is just another barrier to writing. By browsing all my chapters in various states of doneness, I’m more likely to pick one that is going to tickle my writing fancy: Oh hey, I have something to say about this today. Those ceramic mugs have to wait.

A Table of Contents

At some point, it’s a book. This moment is entirely dependent on you, and the best advice I can give is that you’ll know when it happens. Perhaps it’s a critical mass of chapters. Maybe it’s the discovery of one key thought in one paragraph. The point is: you’re no longer actively thinking about not writing a book, you’re writing a book.

Congratulations. It’s time to get organized.

Once you feel you’re actually writing a book, it’s time for a table of contents. I exclusively use a spreadsheet for this task because it’s flexible as well as being good at math. My table of contents starts with three columns:

  1. Chapter Number
  2. Chapter Title
  3. Notes

I then dump whatever chapters I have into this spreadsheet in whatever order feels right. There. Now, you have a table of contents.

There are all sorts of interesting ways to stress yourself out with this spreadsheet. Word counts, chapter counts, percent completes. There’s going to be plenty of time to do this when your editor starts with their kind yet passive aggressive threats, so my advice is stick to three columns for now.

Like many of your chapters, your table of contents is a work in progress. When you finish a chapter, when you’re inspired, or whenever the mood suits you, fire up the spreadsheet and read your table of contents. Are the titles right? What chapters are missing? Which ones don’t make sense?

As we’ll see in a moment, the closer you get to a final first draft, the more your table of contents becomes an essential specification for your book.

See It

Ok, it’s really a book now. 20 chapters, right? Feel like you’re beginning to repeat yourself? Getting annoyed by the sound of your voice in your head? Thinking about writing an article about How to Write a Book? Yeah, that’s pretty sweet.

There’s a painful threshold when you’re roughly two-thirds of the way through the book where you need an extra shove. My advice is to not write an article about this experience, but rather print out the whole damned book. That’s right. Every single page. If you haven’t already invested in a home laser printer, now is the time. You’re almost an author, dammit.

Seeing all of your work spread out on the floor of your office is cathartic.

You’ve spent the last few months (sigh, years) staring at the words and being lost in the paragraphs, so there’s a good chance that you’ve forgotten what you were up to. Look, there on the floor, you are writing a book.

Now is also a good time to make another pass at that table of contents. The sense that you’re repeating yourself in your writing is a good sign that you’re begin to tie up whatever stories you were intending to tell. The combination of the ready availability of all your writing on the floor and the structure of your table of contents makes for a constructive opportunity to see precisely where you’re at regarding your book. Does it fit together? Is it obvious where the holes are? Are there plans to fill those holes? Do you actually have an ending?


This is the last piece of advice and you don’t want to hear it because what I’m about to tell you is depressing. If you haven’t written a word of your book — if it’s just a great title — you are two years away from being anywhere close to done. I base this opinion on entirely unscientific evidence of (almost) having published two books.

Two years is forever, but I’m going to turn it into an opportunity.

Writing is a game of inches. No author I know sits down every morning in their home office and steadily produces three pages a day. I’m sure they’re out there, but these annoyingly efficient and profitable authors aren’t doing this on the side. They’re doing this because they’ve written enough to make it a career.

While the idea of writing books for a living is appealing, my impression is that if I stopped being a software engineering manager, my voice would quickly become an echo of how things used to be rather than how they are. Thanks, no.

You have time. In fact, you have lots of time. There will be weekends where all you will find is a paragraph. There will be a week where all of your progress will circle around finding precisely the right title for chapter 12.

In writing a book, you’re going to find all sorts of interesting ways to mentally beat yourself up. You’re going to consider new tools and different writing schedules. You’ll discover that inspiration can be encouraged, but never created. You’re going to find constructive ways to procrastinate and your friends are going to stop talking to you because all you talk about is that damned book.

Super. In the meantime, let’s write.