My Book Writing Habits

“You should write a Medium post on how to write a book,” Derek said.

“Ooo. That’d be fun,” I thought, “Except I’m in the middle of writing a book and have no time.” But then I realized that one of the great things about my approach to writing books is that it actually leaves time to write other things. And I’m not alone. The New Yorker recently wrote about Trollope:

…three hours a day is all that’s needed to write successfully. Writing is turning time into language, and all good writers have an elaborate, fetishistic relationship to their working hours. Writers talking about time is like painters talking about unprimed canvas and pigments.

And so, here I am, 4:05 PM on a Friday, feeling like the lord of the manor. All my daily goals are done. I have a few hours before I need to make dinner for my wife. And so, yes. Yes. I will write an article on how I write a book. The more I thought about it since Derek suggested it, the more I realized that the tips and tricks I’ve learned to speed the process are as important as the knowledge, creativity and hard work (“turning time into language.”) We can say that the tools of the trade are just pen and paper, but that’s like saying music’s tools of the trade are just a voice and an instrument. Tell that to Drake. Or Max Martin. Knowledge of the tools is vital, as is a mastery of habit.

Note: I am concerning myself primarily here with non-fiction books. This is because I have published one, written a second, and am working on a third. I’ve tried my hand at fiction, and while I’ve succeeded at novellas, I have yet to complete a novel. I’m going to keep at it. And while I’ve yet to succeed, many of the tactics I outline here made my last attempt so much more successful than my first, so I have a hunch that they are applicable to fiction, though it’s admittedly still a hunch.


Write. Always Write.

In many ways, the process seems so straightforward. You’ll find a million quotes about how to write a book, and most of them revolve around the basic concept of “just write.” Write, and don’t stop. It’s like Douglas Adams’ maxxim that the secret of flying is to jump at the ground and miss:

There is an art, it says, or rather, a knack to flying. The knack lies in learning how to throw yourself at the ground and miss. Pick a nice day, the guide suggests, and try it.
The first part is easy. All it requires is simply the ability to throw yourself forward with all your weight, and the willingness not to mind that it’s going to hurt.
That is, it’s going to hurt if you fail to miss the ground. Most people fail to miss the ground, and if they are really trying properly, the likelihood is that they will fail to miss it fairly hard.
Clearly, it is the second part, the missing, which presents the difficulties.

The key to writing a book is to write. Or, rather, to write every day. I mean, sure. Yes, you can miss a day here and there. But you should strive towards writing every day. Fit it into your life. Make room for it. Make time for it.

There are many tools for this, but I would like to introduce you to just one: 750 Words.

750 Words: A Site devoted to private writing, by Buster Benson.

My friend Buster Benson built this site, and I cannot thank him enough for it. It has literally changed my life. Now, I have always managed to write every day, at least for the last 30 years or so. The problem was that I always wrote for an audience. I wanted my writing to be productive. And it killed my writing. As much as I miss the old days of Livejournal where a wonderful, supportive group of online friends nurtured each other and their writing, the fact that I was writing for an audience stunted my writing. 750 Words is private writing. In this world of sharing too much, there are virtually no sharing features on 750 Words. You can tweet out that you wrote that day, and maybe a few stats, but that’s it.

The interface is free of distractions. The lack of an audience makes it easier to try new things, to ramble, to bitch and moan to just get the words out. There are days that it is so painful to keep writing that I literally write “I don’t know what to say,” or words to that effect, over and over until I am done. This will happen to you, too.

There are other days that I wrote something brilliant that came out of nowhere. Many of my best and most successful Medium posts, such as The Economics of Star Trek, and Life as an Arcade, started as 750 words entries.

This is an important point: it’s okay, after you’ve written, to share the writing somewhere else. The point is to have no agenda when you set out. If it turns out, great.

750 Words is part of my morning routine. I do my exercise in the morning, check my email, and do my words before I go through much of the day. In other times in my life, I have done it on lunch breaks, on long walks, or last thing in the evening. It can function as a journal entry, it can function as therapy. Sometimes I take a pause and use my 750 Words to write a longer email to a close friend that I know needs to be done.

And sometimes, when I am working on a book, 750 Words warms me up, much like a morning stretch. I might be stuck in the book and it’s bothering me. So I will pause and do my 750 words, and bitch about how I am stuck. Nine times out of ten, just writing about the blockage, rather than trying to write the book, will unclog the blockage.

Make 750 Words part of your life. Write every day. The site will remind you to do it. There are little gamification tricks to keep you incentivized to keep at it, and a nice community of writers who, while very much in the background, still inspire you with their diligence. It still needs an iOS app, but if you add the site to your home screen, it can pretty much feel like an app. Protip: Set the time zone setting so that the end of the day is after you go to bed, and not midnight, if you like to do late night writing like I do. I have my 750 words turning over to the next day at 4 AM my time.

{iOS/Android note}

You will find my comment about 750 Words not having an iOS app will be a recurring theme in this article. Many of the best writing apps are bound to the desktop. I suppose this makes sense, as many people still feel the need for a full-sized keyboard when writing. But I do think that as tablets and phones slowly replace our computers, this will change. The specific tools aren’t set in stone. It’s the habits and developing a workflow that are important.


When writing an essay, or a blog post (god, definitely a blog post), it’s often the case you can just bang it out without doing a bunch of advance reading. This is almost never the case with a book. The odds are very slim that no one’s tackled the topic you’re tackling. Even if you are writing an autobiography, a working knowledge of the various forms of autobiography is somewhat essential. My first book, Agency, was a book that took my twenty years of experience in the ad industry and offered concrete advice on agency management. It was, in theory, as much of a book of “just type down what you know,” as can be. I still had to read dozens of books to complete it. The point is, you are going to have to read.

The reading time for your book is separate from the writing time. You will need to do both every day. Typically you need to read the books ahead of the writing, though we don’t always have that luxury (new things are being published every day, and you will undoubtedly eventually experience the unpleasant sensation of someone publishing something super relevant to your book when you are in the final stages of editing.) Generally speaking, though, you want to do your reading before you do your writing. If you know the topic in and out, and have been living and breathing it for years, you may be able to start writing without doing additional reading. However, you’re still going to find yourself needing a specific quote, and it’s much nicer to have it on hand than to have to go dig it up and mess up your flow.

When you’ve gotten really good, you might get to the point where you’re writing one book, while reading books in advance of your next book. This is a pleasant sensation if you prefer to not live and breathe a single topic your whole life, but can also be distracting. I typically pick up a new topic in depth when I’ve reached the editing stage. Or, well, I aspire to. Hasn’t quite worked out that cleanly yet.

Analog v digital

Various people have various opinions on reading paper books or kindle books. These biases are going to accompany you into this project. This is okay. However, you should prepare yourself now for having to read documents & books in both formats, regardless of your preferences. And you’ll need to develop a workflow for each format. Some books are only available on paper. Some books are $100 if you buy the one copy on Amazon of that 1912 out of print book, but are free in Google Books.

Books, Research Papers, Articles

You’ll also be reading many different types of documents. This will necessitate different workflows. For example, I prefer, when possible and affordable, to read my books on the Kindle. However, when reading a scholarly paper from an academic journal, I typically receive these in PDF form. These are much harder to read on the Kindle, and not only that, I can’t take notes or highlight in the same way. You will need to develop a workflow for each type of document.

Note Taking & Highlighting

From all of this reading, you are going to need to draw quotes, and remember what was in that book. When I first started, I made the rookie mistake of thinking that I could do all of this in my head. You won’t be able to. Assume from the beginning that everything you are reading will be forgotten. Learn to take notes. The important thing when finishing a book or other document is to make sure that when you’re done, you have marked up the document thoroughly, so you will be able to quickly find anything you need in the future.

The old fashioned process for note taking was to use a pen or a highlighter, highlighting passages and taking notes in the side. I still find myself very (occasionally) doing this. However, for me, I prefer to have these notes digital as soon as possible since, as you will see, the goal is to get all of them into a digital form as quickly as possible.

This can lead to some absurd situations. I take pictures of the screen of my Kindle. I take photos of books. Whatever it takes.

It’s important that all of these notes and highlights end up in one place. In the old days, when I was a kid, that meant note cards for each note and highlight. These days, for me, it means Evernote.

Evernote is the grand central station of book organization.

Evernote is the grand central station of book organization. Everything you are going to put into your book can and should go into Evernote (or some other equivalent product — I’m sure they’re out there, but.. Evernote!) Evernote works on desktops and mobile. This makes me prefer Evernote over the powerful book writing tools we’ll talk about later. Evernote is highly configurable and customizable.

The first important thing to do is to set up several notebooks in Evernote, where you are going to store your notes. Notebooks in Evernote can nest, so you can have a folder for your entire book project, with various notebooks. It might look something like this:

From here, it’s simply a matter of making sure that every note goes into the right notebook. Let’s walk through a few workflows to get there:

For Kindle books, I highlight and take notes using the internal highlighting and note taking tools built into the Kindle and Kindle apps. I then use the Kindle desktop app for Mac, open up the book, and go through my highlights:

I copy each highlight, and paste it into its own Evernote note. Note: this is kind of nice, because when you do it, the Kindle App helpfully appends a source to the copy and paste:

Note that the Kindle helpfully pastes an attribution, along with the page number. Also note that you can plug your Kindle into your computer, and grab an .XML file of all your highlights. You could theoretically find some automated way to do this into Evernote I suspect, but I do it manually because a) I’m not that tech savvy, and b) I often find that notes and highlights may go into different notebooks.

For PDFs, I use an app called iAnnotate on my iPad, or just the Preview app on the Mac, to highlight portions of PDFs and to make notes on them.

I use Dropbox for all the files related to my book, and sync it between my computer and my iOS devices. iAnnotate allows me to take a PDF out of the “research” or “to read” folder I have set up alongside my book, make edits, and save it back to that folder. From there, I can quickly scroll through the PDF on my desktop, and copy out any highlights and notes into Evernote. I SHOULD do this immediately upon finishing the document, but at least even if I forget to, when I go back to the document, all the important bits are highlighted and my notes are right there.

For articles on the web, I use the Evernote plug-in for my browser. Gosh, is it great:

Find an article, click the Evernote icon in your browser, and you’re confronted with a whole range of options. One thing I love is the “simplified article” setting, which strips away all the crap and just gives me the article:

You can also select the notebook you want to put the article in, and add tags. And, best, because this is an article from the web, Evernote will keep the URL and title, making citation easy.

Paper Books and magazine articles are undeniably the most difficult to get into Evernote. The main challenge for me is to get the note quickly into the digital space, without disrupting my reading and thinking. I have two approaches. First, I may read the book with a highlighter or pen, marking up the book as I go along. i.e., the old school approach. After reading it, I go back and transcribe the notes into Evernote. There are several things that suck about this. First, you can’t do it to library books. Second, you need to have a highlighter on your person. I don’t always have a highlighter on me.

Captio is the best

But you know what I do have on me all the time? My phone. It’s time to introduce you to my favorite little app, jack of all trades, best buddy and home screen denizen: Captio.

Captio is an app that lets you rapidly email yourself something. That’s it. Deceptively simple. But so powerful.

First, you can email photos. So when reading a book and I stumble upon a highlight, I can whip out Captio, take a picture of the relevant passage, jot down a quick note, and email it to myself. This is wonderful.

And getting these notes into Evernote is a breeze. Because you can set your Captio up to email automatically into your Evernote. Oh my god, it’s the best. Here’s what I do. Following these instructions, I set it up so I can email into Evernote, going into a default notebook. Then I set up Captio to email to that address and my personal email address. I do this through a quick Gmail forward hack. If I only used Captio for emailing myself notes from paper books, I wouldn’t need to do this, but turns out I use Captio for everything. (Thanks to Michael Galpert for telling me about Captio years ago. Seriously. It changed my life).

You can also set things up to automatically tag the notes, but I don’t bother. I just have all of my Captio notes sent directly into evernote into a notebook called “Random Captio Emails,” and then occasionally parse it, placing the notes into their various appropriate folders. This is such a powerful life hack. More on this in a moment.

Best of all, you don’t need to carry a highlighter, there is no transcribing (until later, and then only if you’re directly quoting the source), and you don’t mark up your books. My condolences to future historians who have relied on personal, note-riddled copies of books for autobiographical source material.

I also use this technique for paper magazines.

People who value simplicity could well point out here now that I could also use the Evernote mobile app to take my picture and notes, and bypass the Captio step here. That is very true. This step also has the potential bonus of allowing Evernote to use its text recognition technology to do the transcribing for me. The reason I don’t take this approach is because I value Captio’s rapidity. It lets me go right back to reading within seconds. Evernote mobile is a great app, but it is harder to create on it than the desktop app, which has many wonderful features such as a distraction-free writing mode. However, I find it very time consuming to open the app, select new note, assign it to a notebook, click on the photo, click on the document-scanning mode, and take the photos. Captio gets me back to reading more quickly, which it my nominal task at this point. Your mileage may vary.

Don’t Forget the Book Report

I have also learned that the best thing to do when finishing a document is to immediately write a quick book report on it. I do this in my 750 Words the day I finish the book. Oh, dear god, I wish I had done this sooner. It is the best. If you’re dilligent in this one thing, in many cases you can have a third to half of the book done before you even begin. Trust me, it is glorious.

Do this as soon as possible. Preferably within a day or two. Don’t bother to look too much at your source material, or mine it for quotes. Just get your thoughts and impressions down. Do it like you were telling a friend. Don’t worry about “book voice.” By writing down your pure, unfiltered thoughts on the topic, you’re getting your point of view about the work. Not what other people want you think, and not what the book says itself necessarily. This is original work!

Creativity and Inspiration

We’ve tackled how to consume and parse third party material, but there’s also your own thoughts and material to contend with. This really comes down to two parts: getting your thoughts down to paper, and getting them organized. Let’s tackle the first here.

Even when we know a subject well, it is often hard to remember everything we know about it. When starting to write Agency, I first tried to just write down everything I knew. Seems simple enough. Turned out that even a year later, as I was finishing up the editing, I would suddenly remember a whole topic I hadn’t mentioned that was important for the book.

Thoughts are going to hit you all the time. I often think of a thing I need to get into my book as I’m falling asleep, cooking or on a walk. These are important to get down right away. It’s easy to think that it’s so important you will remember it, but you won’t, and few things can be as frustrating.

(I should pause for a moment to say that Evernote has a wonderful line of paper, analog notebooks in partnership with Moleskine that could, theoretically, provide as flexible and awesome an interface as my Captio-to-Evernote workflow. I haven’t tried them. But I always mean to. I guess that’s the evidence in itself I don’t need them. Because it’s just another thing to carry. It’s another thing to have on hand when the moment strikes. Also, we are writers, we use words. And I can type words. I can see the Evernote-Moleskine combo being hugely useful if you are in a visual medium. Our goal here is to get words down. )

Again, Captio comes in handy here. Have it on hand all the time. When in the thick of writing a book, I send myself literally a dozen notes a day. This morning, while on a walk, something hit me and I jotted down a 200 word Captio note. I felt awesome when I started today’s writing having that head start.

Walk walk walk

On that note, go for walks. Get away from the computer. Do things. A book, no matter the subject, is an expression of creativity. Creativity does not only happen in front of the computer. It happens at the movies. It happens in the kitchen. In the bed (bom chicka wow wow). Be ready to get it written down the moment it happens.

There exists, of course, the risk that you’ll spend too much time on the “creativity” and not enough on the writing. But this is where routine comes in. We’ve touched upon this with our 750 Words habit. We’ll expand upon it when we get to targets.

When spontaneous words become books

We should also point out that our 750 Words habit, even during the research and discovery phase of a book, can yield whole chapters of a book. If the mood strikes you one day, and you’ve written on the topic of your book (as opposed to about your day, your love life, or how hard it is to write — a surprisingly popular topic I’ll wager), copy and paste it out of 750 Words and into Evernote.

Organizing & Outlining

Once you’ve read all your source material, and captured a large amount of your own personal thoughts through inspirations tapped into Captio, unexpectedly genius spontaneous 750 Word entries and the like, it’s time to get everything organized.

Of course, in a way, everything is organized, in Evernote. In a way. But now we take it to the next level. It’s time to outline your book.

It is here I introduce you to a new piece of software I couldn’t live without: Scrivener.

Scrivener, a bookwriter’s best friend

Now. Before we go any further, I need to warn you that Scrivener is only a desktop app. Their attempts at developing an iPad app have been long and miserable. It is really sad. The company is getting close to being completely moribund. This may matter to you. What I have found is that for me, the need for an iOS version of Scrivener is more academic. I rarely write on an iOS device, and when I do, I write right into Captio, sending it to Evernote, or I write my 750 Words. However, I am a well off dude that owns, like, 6 Macs, and has been typing on a full sized Apple keyboard since 1983 or so. Some people can’t afford a full Mac. And some people are more comfortable typing on screens, or mini keyboards, than I am.

If these are concerns of yours, there are two up-and-comers who you should consider. The first is the aforementioned Evernote. They seem to be working very hard at turning Evernote into a viable option for book writing. My friend Nicholas Carlson wrote his whole book directly into Evernote. The second is Storyist, which is essentially a new version of Scrivener that actually also has an iOS version. Storyist also seems to be a bit more robust if you are writing screenplays.

Storyist is like Scrivener’s young, attractive sibling.

I stick with Scrivener because: a) the current book I started was 3 years ago and this wasn’t an issue as much, b) Evernote is built for so many people doing so many things that they are very slow to iterate on longform-writer specific features, such as Kindle export, and c) I can’t live without targets (more on them later). For my fourth book, I will probably move over to Storyist if Scrivener hasn’t come around. I’ve also had a hankering to try a screenplay out, so all the better.

All that being said, Scrivener is still awesome. If you had visions of writing your book in MS Word or Pages, give them up now. While Scrivener has many strengths, one of them is in content organization. It’s so good, that there have been times I have thought about abandoning Evernote completely. Scrivener has many of the same organizing features (including great web clipping organization). But in the end, Evernote is a large, iterating company, and Scrivener isn’t, so… I use each tool for their speciality. I, along with many writers, dream of one tool to rule them all, but I suspect it’s a long way off.

Anyway, Scrivener’s organizational tools are superb. Note cards, outlining, everything you need. Lots to learn. I have spent hours of my life watching Scrivener tutorials, but it is so, so worth it.

Some of Scrivener’s organizational tools

Whatever tool you use, the goal here is to outline your book. At a minimum, make one document for every section. Not every chapter, every section. The more granular the better. All of these tools allow for nested documents, and include folders. In the end, you want your outline to look something like this:

Outlining is vital. You want to break it down so every section is (not coincidentally) 750–1,000 words. You’ll find many of your outline topics from your inspirational Captios, such as “don’t forget to write about x.” Go ahead and make X a section. Make major book reports sections. Make anything you can think of it’s own separate section. Keep adding them. You may kill a few later, but add all that you can think of, for now, and then organize them.

A Scrivener Outline

This does two things:

  1. It decouples the act of writing a section from deciding where to put it. You will change your outline hundreds of times. That’s okay. When you do, the work that you have written will move with it. Yes, you may need to tweak transitions here and there, but your writing will still be intact.
  2. It breaks down each larger section into smaller, more easily writeable chunks. This is the first, major break in transitioning from thinking of your book as one long document to a series of smaller documents.

This is huge. The importance of this cannot be overstated. A journey begins with a single step and all that yang. No one can look at a blank paper and start writing. Actually, I saw that happen once in a documentary. A famous screenwriter had finished his film and he sat down to start the sequel, and typed out the name on a blank piece of paper, like he was gonna write the whole thing in order. You know who that was? George Lucas. Revenge of the Sith. Do not let this happen to you.


While this whole article can seem like an exercise of walking in circles around the prey instead of attacking the prey, that is exactly the point. The prey is much, much bigger than you. You need tools, you need weapons, you need to study it, be prepared, and find its weaknesses.

Then we attack.

Setting Goals and Targets

At this point, we write. We write a set amount each day.

And, truth be told, it’s not much. Let me introduce you to another vital feature: Project Targets.

These are the best! Here’s what you do. You set a deadline, you set a word count, you tell it what days you want to write, and a few other things, and Scrivener automatically tells you each day when you hit your goal. It is AWESOME. It gives a little beep each day when you’ve hit your target and it is the best feeling in the world.

If all has gone well, you will write one section of the book per day, and those sections will be about 750–1,250 words. It will never align this perfectly, but those are good guidelines.

On a good day, when I’m hyper and productive, I can hit it in 30–40 minutes. On a bad day, when I have NOTHING, I can hit it in a couple of hours.

So, yes. You can write a couple hours a day and finish a book in no time. Look at my targets. I started this book, in earnest, about 3 weeks ago. I want to finish this draft 10/1. It’s not bad at all. I also set my target for 100,000 words even though I’m writing an 80,000 word book because I want to leave room for editing.

That’s all you need to write in the day. Sure, there are times when you find yourself on a roll and doing much more. This can be good. I find that it’s not always good when writing non-fiction, as often what is actually happening is you’re writing parts of other sections of the book and you’ll have a miserable time merging them later, when you write that section. With fiction, I find that an inspirational bout of writing a lot more is almost always good. Roll with it. But don’t sweat it if it doesn’t happen.

Find a Routine

So, a typical writing day for me will look something like this:

  • I wake up, have a quick breakfast, enjoy the morning for 30 minutes.
  • I go on a long walk. I listen to instrumental music, mainly, from a Spotify playlist I have of “writing music.” (I warn you some of it is noisy). I look at the trees. I people watch. I write notes into my Captio, some about the book I’m working on, some not.
  • I go home, and I do my email and whatever else needs to be done for my part time day job.
  • I write my 750 words.
  • I write my words for my book. Sometimes, my 750 words all but did this for me. Other times, this can take a few hours.
  • I do other things. I read, I cook, whatever. I read before bed, on trips, and if a day goes so perfectly I finish everything else early.

Lest ye think this is the life of privilege and leisure and oh man how can you do all that without a job, this was my routine while holding down a job as a very busy internet executive:

  • I woke up around 7:30, I got to work around 8:45. I took notes on the subway, and read on the subway.
  • I worked all day.
  • I wrote my words for a book during my lunch break. It was a very short book — 50,000 words. I needed to do about 750 a day. I used the organizational techniques here, which I laid out in advance, on the weekend, so all I had to do was get my words down in my break.
  • I walked home, which took about 45 minutes. I cleared my head, thought about my writing, and took lots of Captio notes.
  • I made dinner, and did my 750 words after dinner.

You can find a routine. I have friends who have three kids and still write books and hold down jobs.


Once your book is done, you will need to edit it. I believe editing deserves its own post, but I will say a few words here:

I believe it’s better to over-write than to under-write. Cutting your work can SUCK, but it’s better than not having enough.

I export the whole book to PDF from Scrivener, and then use iAnnotate to read the book, highlight, mark edits and changes, and comments and notes for myself. I do this at least twice before I let anyone else read it. It can suck, because once other people are in the equation, your book can still radically change, and you’ll think “why did I polish it that much before I gave it to someone else?” But I still feel it’s the right thing to do. Better to show people something more polished. I hear stories all the time of people who let people into their writing early, and I’ve just not had much luck with that. I need to get my vision down first. You may find a different approach is better.

Then comes the real editing, which involves usually, a ton of cutting, some painful re-writes, and at least one major re-organization. That’s okay. Because, through this whole portion I am just thinking “whatever, I’ve written this book. I did the hard part, I can do any of this.” Major re-writes can be accomplished via similar means described above. Major reorgs will occur to you on walks more than once. Eventually you’ll need to settle on one outline until you make final decisions with your publishing editor, if you have one. If not, you can do whatever the hell you want. Maybe ask a friend. Maybe not. It’s cool. Because you wrote a book. Congrats.

PS: It’s 6:45 PM. I also took a call in that 2 and a half hours. I wrote this today because my conscience was clear after a beautifully executed day of routine. It was a lucky day, they are not all that lucky. I will still have to edit this before I publish it, but… hey. It’s done.

PPS: And now it’s Monday, I’ve given this an edit, and tweaked about 5–10% of it. There are probably a load of typos, but I trust you guys will point those out for me.

PPPS: If you enjoyed this, I have also written a piece on My Reading Habits.