Nothing unfamiliar (Tools I used to write a book)

My book advises designers to be intentional about the tools they choose and use to do the writing on their projects. For writing a book, a thing I’d never done before, I ran a few experiments to see if there was any good and smart tool I hadn’t tried before that would make it easier. I quickly learned that I didn’t want to use anything new. The book was not an experiment in tools. It was a job. I had work to do, so I went with what I was familiar with.

That’s now also the advice I give to people planning their own book projects:

  • Write wherever you can write quickly.
  • Keep notes however you’re used to keeping notes.

You’ve got a book to write; you don’t need a new part-time job as librarian or software developer or project manager, too.

It’s been a minute since I wrote the book, but I’ll run down everything I can remember using.

MindNode

MindNode has been my outlining and braindumping tool of choice for over a decade. It has a limited featureset and good keyboard control and lets me work quickly. I worked up various versions of the initial outline in MindNode, and would open it up here and there throughout the process to think through something or generate a detailed outline for a section or concept before trying to write it.

Byword

Byword on MacOS was my typewriter. It was the primary tool I used to produce the first complete draft of the manuscript. Byword is a plain text writing environment with Markdown support, which means that you are mostly just typing while you write (and not fiddling with margins and fonts and formatting and such).

I organized my draft as six plain text files: four chapters, the introduction, and resources. I also had a scratchpad file.

I ran ByWord fullscreen on a 13” MacBook Air I was carrying at the. Fullscreen enables multiple tabs of ByWord on one screen, like tabs in a web browser. I opened the scratchpad document as my first tab, and then each chapter in order. This way, I could have my entire manuscript open at once without having to do too much scrolling. I mostly worked in a non-chronological order on the book, and would often find myself needing to move things from one chapter to another as the structure evolved.

Google Drive

I used Google Drive to draft the bullet-pointed, Table of Contents-style outlines that were part of pitching the book and refining the initial concept. I also used it whenever I needed to share something with someone, often copying as rich-text from Byword, pasting it in, and cleaning up as needed.

Google Drive was also how I coordinated marketing for the book, with a variety of spreadsheets and documents, and some light email automation in Gmail.

Dropbox

Dropbox was my safety net for the drafts and revisions. I kept all my text files in a Dropbox folder, which to this day are still inside a folder called “Digital Writing Book”. I didn’t have to think about Dropbox and that’s what I like about it.

Microsoft Word

I would prefer, personally, to never use Microsoft Word. I just don’t want it. But it was part of the revision and publishing process, and I used it as needed. The publisher provided a Word document with all of their styles and formatting conventions built into a template.

When my first draft was finished, I copied each chapter into Word as plain text from the text files. I then went through paragraph-by-paragraph to clean it up, apply styles, add bolding and do some light copyediting here and there. This sounds tedious but it really didn’t take long at all, maybe two hours for the whole book, and I found this vastly preferable to using Word during the initial writing process.

My editor and I collaborated on drafts in Word with comments and track changes.

Field Notes steno notebook

On one of my early writing sprints at Open Book I felt constrained by only being able to type my thoughts. I didn’t have a notebook with me so I popped into the gift shop and got a steno-style Field Notes that they had in stock. There were only a few options, so I decided to suffer Gregg-ruled paper (ugh) in exchange for the lay-flat top binding (yay!).

The notebook stayed with me throughout the rest of the writing process, and I only put things about the book in the notebook.

When I ran out of steam typing I would noodle a bit with pen and paper until I got unstuck, and then resume typing. It helped ideas flow more easily; whatever I was writing on paper wasn’t something I was committed to, which I think help relieved some pressure and helped ideas flow more easily.

I kept to-dos in the notebook, and would often make notes to myself about what I’d done on a certain date and what I wanted to do the next time I sat down to write. It helped to keep a conversation with myself about the book without those thoughts cluttering the actual draft.

Long paragraphs

“So often the long paragraphs I write in life are responses to Facebook posts, or reply letters to someone, or … I can put together a three-paragraph letter that burns the hair off of your eyebrows about almost any topic.”

– John Roderick on the Road Work podcast

I like this thought technology: Where do the long paragraphs come from in your life?

A long paragraph isn’t a good or bad thing, but it is instructive. It points to a passion, a pain point. A bugaboo or a peeve. If one pops up while in a piece I’m writing, it’s often a sign I need to expand — more structure, maybe another section. If one pops up while I’m using social media, it’s often a sign I need to shut my computer and go take a walk.

Islands and icebergs

Spent all week working on something and I just trashed it. Wasn’t coming together. Hate to do it because you never know if you were almost there. Sometimes you’re hating it and hating it, and you keep sailing on, and then blam-oh! There she is! I see land, boys!

But maybe you stopped just before the iceberg. This one felt like an iceberg. The idea seemed reasonable enough, a good thing to write, that would get some shares, generate engagement. I’m not above writing for engagement, but I don’t want to hate myself while I’m doing it. This one just wasn’t feeling like me. I think. Unless I should have kept sailing.

Good news is I’ve still got the boat, and a little more practice sailing than I had before.

Painting a very long hallway

I’ve been asked a few times what writing a book was like. Sometimes people mean: “What’s it like to be someone who wrote a book?” It’s nice! Glad to have done it, glad to know I can do it, lots of new opportunities, nice to have something unambiguously mine, and so on.

It’s interesting to ponder the question as asked, though. What was it like to write a book? Act of, not fact of.

Practically speaking, writing a book was a lot of sitting in a room alone and typing. (And not responding to emails.) Boring! A simile, then: Writing a book is like painting a very long hallway.

It’s like a very long hallway – and not, say, a bedroom, or even a Bob Ross landscape – because you can’t see the scope of the effort all at once. My paint roller only reaches so far, but I’m trying to get a good even coat from beginning to end, across many weeks of effort. This was the most different aspect of the work compared to, say, an essay or newsletter.

There was a lot more prep work than I’d imagined, even after I thought I was totally prepared to start. Picking out paint colors was so fun, but now, oh God, is that more wallpaper under the wallpaper?

Once you’re actually finally ready to start, later than you’d have liked, the hours tick by. Mostly, you’re painting. When you’re not painting, you’re thinking to yourself, “That hallway isn’t going to paint itself!” And it doesn’t.

Some days you hit a rhythm and there’s a beautiful shluck, shluck, schluck sound as paint rolls on in big even swaths. Or perhaps, after a week of not painting, you spend all day trying to get the dried out lid of the goddamn paint can off. Some days you paint for hours only to realize that can was off-white, not eggshell, and, well, guess I’m doing that part over.

Sometimes you paint in the middle of the night, because painting the hallway isn’t your day job — and it’s not your social life or self-care — it’s just this other thing that you do.

Sometimes you spend all weekend painting the hallway, because you never got around to painting during the week and you promised you’d be done with the first coat by Monday, Tuesday morning at the latest.

By the end — the paint dries so slow — by the end, you’re loopy on fumes. Everything you own is covered in paint. But it’s done, damn it! Ahahahaha, the fucker is done.

Except, wait, that was just the first coat. Oh no. You missed some spots! Let’s do it again! And again! Prep, sand, paint, tidy, prep, sand, paint, tidy. Eventually, you just have to decide that it’s done, that the crimes are well enough hidden, and that it’s time to peel the tape, put the furniture back, and re-hang the family portraits.

This isn’t to say it isn’t enjoyable. Painting is laborious, yes, but it can be rewarding, even hypnotic. But however pleasant the hours, the best feeling is still being done with it.

Being the thing

Composite screenshot of November and December calendar pages in the Streaks app for a goal of "60m Writing". November 25
Overslept on Friday. Womp womp.

Recently finished reading Stephen King’s On Writing: A Memoir of the Craft. I probably should have read it before I wrote a book about writing? But I’m happy to report it didn’t leave me second-guessing my guidance in Writing for Designers. Just envious of King’s prose and storytelling skills.

Like many books on creative practices, much of the advice can be reduced as such:

to be the thing (e.g. writer)

do the thing (e.g. write)

and do it every day (e.g. today, and also tomorrow).

Novelists often recommend daily wordcount goals as a way of approaching the doing part. King suggests 1,000 words a day and building up from there. That makes sense to me if you’re writing a book manuscript. A book is a big hunk of marble you’ve got to chip away at daily. I’ll probably try daily wordcount goals when I’m committed to my next book.

Thing is, there’s quite a bit of non-book writing I’d like to be doing. Essays and articles and blog posts and newsletters and the like. I’ve tried wordcount goals for this kind of stuff in the past and it doesn’t work for me. Telling myself I’m going to write 1,000+ words of whatever per day has led me to write exactly that: a bunch of whatever. Hell, my first book draft was twice as long as they wanted. Quantity of words written is not the problem.

Of late I’ve been trying a different habit, and the results are encouraging. For 15 out of the last 16 days, primarily in the morning, I’ve started a one hour timer. When the timer is running, I am a writer. I am practicing being the thing.

Most of what I do during this hour is, in fact, writing words — as fast as the Gingerbread man runs, as King puts it. But I might also be editing things I’ve written, or reviewing my Ulysses and Drafts inboxes to find what I want to write next, or turning finished drafts into stuff other people can read.

Focusing on the hour instead of the output is about committing a serious part of my day toward living the life I want. When I am being studious and creative and productive – when I’m reading and thinking and making – I feel great. When I’m not, I don’t. I hope all of this work adds up to something, and helps to elevate my profile and boost my career. But even if it doesn’t, it still feels like what I am supposed to be doing.

This is a more fragile habit than a wordcount goal. I have to be honest with myself about how I’m using the hour. There are a lot of non-productive approaches to being the thing when it comes to writing: shopping for notebooks (guilty), choosing the best music to write to (guilty), researching writing apps (guilty), tweaking shortcuts and workflows (guilty), looking at a looooot of Wikipedia articles in the name of “research” (guilty). I’ve eschewed hard rules so far during the hour, but I do try to be really and truly settled before I start the timer – email checked, coffee made, bathroom visited. I also turn off Wifi. (Turning it back on here and there to grab a link or publish a post.)

The hour is harder to fit into my day than an arbitrary quantity of writing, but that’s part of what’s important about it to me. I want it to hurt a little. I want to have to change things to make it work.

Establishing good habits is hard as hell, especially going from zero to an hour a day. I hope I don’t have to adjust this approach too much going forward, but I’m going to try to be kind to myself if I do. So far it’s helped to:

  • Have a supportive partner who’s also practicing this. We’ve done many of our hours together at coffee shops, and once, adorably, side-by-side on an Amtrak train.
  • Go to bed a little earlier. Harder than it sounds for my dumb ass, but I’m trying.
  • Set multiple alarms. A thing I didn’t expect going into this is that the writing basically has to happen in the morning or it won’t happen.
  • Track my habit in the Streaks app. (It seriously KILLS me that I missed a day and I’m already eager to beat the previous 11-day best.)

Okay. Hour’s almost up. Gonna get this thing ready to publish.

It doesn’t keep

Author's photograph of several pads of paper on a desk referenced in the article.
Various paper pads I keep at my desk. (Ninja Turtle for scale.)

Reflecting on how I use paper and notebooks.

Paper helps me think. I’ve used plenty of Field Notes and Baron Fig notebooks over the years. But truth be told? Most of my notebooks become obstacles, not tools. Three-fourths-filled Pandora’s boxes of contextless notes, forgotten or abandoned to-dos, poems or sketches that I cringe to look back on, and other detritus that reduces the likelihood I’ll ever actually make anything out of what they contain.

Reflecting on this reality has led me to start preferring pads and notebooks with tear-away sheets. I find that I’m more productive and creative by focusing on getting rid of paper.

The mindset I’ve adopted is: Paper gets processed. In a Getting Things Done sense, that means all paper — sticky notes, legal pads, napkin sketches, and (slowly) my former costly notebooks filled front to back with day pages1 — gets treated as one big Inbox. A piece of paper represents Work To Be Done. Paper carries, but it doesn’t keep.

Processing the paper could mean:

  • Trashing it. Deciding that whatever I captured is of no value, crumpling it up, and tossing it on the metaphorical fire. (Or literal, if I’m camping.) This is hard for me with creative writing like lyric ideas or bits of poems … but it’s also necessary. Storing every pleasant word combo that crosses my brain leads to a creative traffic jam.
  • Transcribing it. If the paper has something on it I want to further develop, I might capture and transcribe it into Notes (for songs) or Ulysses (for other writing). If there’s a sketch or diagram or something useful about the form, I’ll snap a photo and keep that alongside the written transcription. Importantly, I don’t let these images stack up in my camera roll.
  • Transferring it. Putting the idea the paper represents into the specific thing it should be: a task on my NOW2 list, an item on my grocery list, an appointment on my calendar, an entry in my Day One journal, etc.

Processing paper — deciding between trashing, transcribing, or transferring — is a productive friction that helps me make. It’s freeing, because I don’t feel pressured to write anything important. It’s focusing, because not every idea I capture goes forward. It’s motivating, because I am gaining confidence in a process that turns random neuron firings into actual Works I can share with the world (and not just abandoned secret scribblings).

I have no doubt that I’ve thrown away paper with marks that could have become good songs, good articles, even good books. But I’ve learned the hard way that if I try to do everything, I end up making a whole lot of nothing.

If this approach is interesting to you, I have a few tips:

  • Keep various sorts of paper handy. Different sizes and patterns suit different types of thinking.
  • Avoid fixed bindings. Could-tear-it-out-if-I-have-to is not the same as loose or perforated.
  • Have a wastebasket handy. If there’s not a fireplace or trash can in your office, where’s the paper gonna go? You don’t want obstacles between you and processing.
  • Find a good processing cadence. I don’t process every notepad every day; the legal pad that lives on my music stand gets processed every few weeks as needed. Bits of paper on my desk get processed at the end of every work day.
  • Use more paper than you’re used to. If you write everything on one big piece of paper it’s very difficult to process, and you may as well be using a notebook.

And some paper recommendations:

  • Ampad gold fibre notepads, 5”x8” – ~$25 for a dozen. I also have some legal pad sized ones. These are nice if I’m working on a talk or client deliverable and need to have several sheets going at once. The relatively thin paper is very satisfying to crumple up and toss across the room.
  • Doane Paper Flap Jotter, small – $13 for a 3-pack. I use these on the go. Normally a very short scrap of an idea goes directly into Drafts, but in some contexts if feels rude or not classy to pull out my phone. It’s also practically useful to carry paper you can leave as a note. I’m not a above a 79-cent drug store memo pad but the Grid + Lines pattern and chipboard cover make these a real treat.
  • Baron Fig Mastermind desk pad, standard – $15 for 2(!). My go-to for when I need to wireframe or storyboard something. This paper starred previously in my post about sketching a blog post.
  • Square memo pad – Varies. The one in the photo is a Neenah Environment Papers sampler that came in a goodie bag at Design Camp. It lives on my desk now. I will be sad when this one is spent, as they seem to not be for sale. I don’t like sticky notes (no shuffle) but I do love a small form factor. These are a bit bigger than a Post-it at 3.5″ square.

  1. Day pages are just what they sound like; I write the date on the top of a two-page spread, and keep a little log in a Bullet Journal-esque fashion. Appointments, things I did or bought, things I ate, etc.
  2. NOW is an Apple Reminders list of next actions it is possible to accomplish that day. I swap tasks between this and a LATER list of things I need to do soon-ish, but can’t or won’t get done that day for whatever reason.

Seeking momentum

A friend who’s working on a new book (hi Corey!) asked if he could pick my brain about book marketing, seeing as I’d recently released one. Most of the advice I was able to share was just stuff I’d learned from others. Abby Covert sent me a very nice and helpful email of tips when I asked. My friend Brian, a great designer, let me pick his brain a while back about how to communicate better with designers and the AIGA crowd. And ABA connected me with Leslie Zaikis, who sent all kinds of lovely checklists and ideas to help launch and promote the book. There were more. And I suspect someone will be picking Corey’s brain a year from now with similar questions for him.

I hope I was helpful. But the truth, as I shared with Corey, is that I feel like I limped over the finish line on Writing for Designers. It was tough because writing is hard, and because it was my first book, and especially because the process of writing the book overlapped with some really difficult stuff in my personal life. I didn’t have much energy to do nearly as many of the promotional things I would have liked to do before, during, and after the launch back in October. Which isn’t to say I didn’t do anything; I organized a launch party, I sent SO MANY emails, I did a webinar for one meetup group and visited another in person, and lots of other little things here and there. But I felt like I’d left a lot still sitting on the table.

So I’m trying to get back to it. A few opportunities have sailed, sure, but October wasn’t that long ago. The book isn’t even six months old. And it just came out in print a little while ago. I’m in a steadier place now, and I’m trying to use this place to build momentum. I know from experience that you can’t force it. A little bit each day, then a little bit more.

So I’ve been trying to write and tweet more, about writing and design, but also just in general. I’m trying to be zen about having done the best I could at the time, even if it was less good than I wanted, and continuing to do the best I can going forward. I think that’s the real best advice I have to offer: do what you can today.