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.

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.

A Year of Writing for Designers

Print and ebook editions of my book Writing for Designers.
Print and ebook editions of my book Writing for Designers.

My first book, Writing for Designers, was released by A Book Apart one year ago today.

Personally, much of the past year has been a blur. I experienced a profound loss in December in the death of my mother, a scant 68 days after the book was first released. Reflecting on a year since the release of Writing for Designers has been investigative for me, in a way. I barely remember being some of these places, and I’m sure I’ve forgotten others.

But the book has brought many wonderful people and experiences into my life, and I’m grateful to have had it as a bright spot, however dark the background.

Here’s what a year in life of the book looks like:

  • October 16, 2018 – Release day. The ebook becomes available for purchase.
  • October 16, 2018Content Strategy MPLS/St. Paul meetup webinar. Delivered my first iteration of How to Get the Writing Done, the talk I reverse-engineered out of the book (and previous workshops) to make the lessons appeal to an audience of more than just designers.
  • October 16, 2018 – Release party. I bought some food and drinks and hosted friends and a few strangers at the Stray Dog restaurant in my neighborhood in Northeast Minneapolis.
  • October 18, 2018A List Apart article goes live. They published the introduction chapter to Writing for Designers as a preview, and lots of nice folks tweeted links and quotes.
  • November 13, 2018UX Book Club Chicago meetup. To my knowledge, this was the first book club to feature Writing for Designers. I popped down for an in-person presentation and Q&A at the very cool headquarters of Solstice.
  • November 28, 2018 – Recorded User Defenders 059. Had a chat with Jason Ogle on a special edition of sorts of his excellent User Defenders podcast. It was released a few months later.
  • November 29, 2018 – UMN Technical Writing presentation. Shared How to Get the Writing Done in a webinar with folks involved in the technical writing program at the University of Minnesota.
  • January 29, 2019Print edition released. A Book Apart put together a way to order ebooks from the Briefs series as print-on-demand paperbacks. This was a lovely surprise not long after the ebook release.
  • February 7, 2019IxDA presentation. Delivered a breakout session of How to Get the Writing Done in the Cinerama theatre at Interaction 19 in Seattle.
  • February 19, 2019Gather Content webinar. Part book promo, part Confab promo. Lots of great Q&A after an updated presentation of How to Get the Writing Done.
  • March 3, 2019AAF CRIC meetup. One of my first road trips after bringing the truck up from Arizona in January! Shared How to Get the Writing Done with a crowd of folks in marketing, advertising, PR, and tech. (And came home with a great bottle of Cedar Ridge whiskey!)
  • May 5, 2019Prime Academy presentation. Been dropping in to visit the UX cohorts with some regularity at this educational bootcamp, and this time I brought in How to Get the Writing Done (and lots of free copies of the book in paperback).
  • June 6, 2019Content Design NYC meetup. Shared How to Get the Writing Done and a few copies of the book with this rad and fairly new content design meetup at Kickstarter’s HQ in the Greenpoint area of Brooklyn.

And next week, I’m heading to PUSH UX in Munich to present a full-day workshop based on Writing for Designers and an updated version of the How to Get the Writing Done talk on the main stage.

The book has an acknowledgments section, to which I will now say “ditto!”. I also shared a thread (or tried to, anyway) of quotes and reviews and other nice things folks have shared since the release this morning on the @DesignersWrite account.

At the top of this article, I called Writing for Designers my first book. That’s on purpose. I don’t know what’s next for Writing for Designers, but I do know that another book is next for me. I was glad to learn that I could get something like this done, and I learned a lot from doing it (from various difficulties and failures as much as any successes).

On to the next one.

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.

Unambiguously mine

My book is in print now. Available in print, anyway. Print on demand. I have a printed copy. (I don’t want to get “you wrote a text”-ed about my book and its relationship to paper. But I digress.)

I did not know this was going to happen when I agreed to write for the Briefs series, so it’s been a delightful surprise. I’m glad it happened relatively soon after the original release of Writing for Designers, too.

I’ve been sharing my thoughts on writing and content and design with the broader UX world for almost a decade now. Long enough to see ideas from my talks and tweets and blog posts get … upcycled, let’s call it … into other people’s talks, tweets, even books. Not maliciously, often not even consciously, I imagine. But it happens. So it’s been nice to be able to look at a thing I’ve made and say: “Yes. This is unambiguously mine. I made it and it exists and it happened and here is the proof.”

A lot of things I’ve done are kind of…squishy. Spaces. Events. Programs. Campaigns. Concepts. All things I’ve enjoyed, but not things I can stick directly on a shelf. I’d collect trinkets; a DMMC lighter, a Gross Domestic Product poster, a Market Day button, “Speaker” badges from umpteen conferences. But trinkets get dusty, and untidy, and they aren’t the thing, just a reminder of it. My dad always talked about how satisfying it was to look back after a day of laying brick and be able to see your labor. (He also liked to take circuitous routes through Omaha so Mom and I could see his labor, too.)

So this is what I’m brainstorming now. How can I render and represent my labors? I’m getting more photos printed, for starters. Even hung a couple up in my apartment. Vain? Sure. Inspiring? Also yes.

I’m incredibly grateful to everyone that’s ordered a paper copy of the book, especially those who already bought the ebook back in October. If you’re one of them, please consider sharing a photo of it on your desk, bookshelf…hell, even on top of your toilet tank. It’s very motivating, and I can always use a bit more of that.

UX Book Club Meetup at Solstice

My friend Michael Metts came out and snuck a few nice photos.
My friend Michael Metts came out and snuck a few nice photos.

Recently back from an overnight trip to Chicago to speak with their UX Book Club. My book Writing for Designers was the featured book, and they hosted a Q&A style event with the author, who is me! This was the first time I’ve been at an in-person event specifically because I wrote a book. I thought I’d be more nervous about it but I never really was, just excited. Blind dates and conference talks are more stressful.

Getting to Chicago

When I first started speaking and embarking on my current career in earnest, around 2012, I was always looking at events like this and wondering: how does that work? Logistically and financially, I mean. Are authors getting paid to do Meetups? (LOL, no.) Are publishers paying to send them there? (LOL, no.) Are authors making enough on book sales from these appearances to justify the cost? (LOLOLOL. No.) For my niche industry book and where I’m at in my career, none of those things were the case. Turns out it’s just a lot of asking people nicely for a bit of help.

As part of the pre-launch marketing for my book, I sent lightly-customized emails to several hundred people (about half of my LinkedIn connections) to say a bit about the book and ask for help. My friend Cate Kompare, a lovely human that I coincidentally met at a different UX book club in Champaign-Urbana many years ago, replied to say that her employer Solstice has been hosting more events, and asked what it would cost to get me out there. I quoted a modest appearance fee for a private event, and said that I could also do it for just travel reimbursement for a public event. They were able to do the latter, and Cate coordinated co-presenting it through the UX Book Club Chicago. Kristina and Brain Traffic have been very supportive, and were happy to handle invoicing my expenses and giving me the time to get down there.

I smashed the trip right into my work schedule. I had a conference call Tuesday morning up until I needed to leave for the airport, and did a bit of work in the afternoon at Solstice before the Meetup started. I was back in the office around 11:30 the next day, and right back to work.

They had a desk set aside for me with some goodies and I got to play-act working at a big company for a couple hours. Someone even came up and introduced themselves thinking I might be a new employee, which was sweet.
They had a desk set aside for me with some goodies and I got to play-act working at a big company for a couple hours. Someone even came up and introduced themselves thinking I might be a new employee, which was sweet.

The flight was about $250, the hotel about $175, and three Lyft rides totaling around $80. I paid for food on my own and took the light rail and bus home from the airport to land closer to the $500 in travel expenses estimate I’d given Cate. (And if I’m not in a hurry, I prefer taking the train home anyway.)

Being the author

I have to admit I was pretty delighted to see this pop up on Google while grabbing directions to the office.
I have to admit I was pretty delighted to see this pop up on Google while grabbing directions to the office.

A couple of days before the event, Cate asked if I’d want to set up a merch table or other sort of display. A totally smart question that caught me off guard. Shit! It’s an ebook! I don’t have, like, a thing! Luckily I still had some A Book Apart buttons and stickers from my launch event in Minneapolis. I made a little display of them and some of my Brain Traffic business cards next to the pizza laid out for the meetup. I’m thinking I might want to get a little poster in a photo frame and a newsletter sign-up sheet on a clipboard, maybe some postcards, for future events. It’s not all that important if people even sign up or take your card, but it does help to make things look more “official” and put together.

Years of Confab experience has made me good at not acting like my picture is being taken while very aware that my picture is being taken. I really enjoyed the conversations during and after the event as folks were genuinely interested in UX writing, not just content strategy.
Years of Confab experience has made me good at not acting like my picture is being taken while very aware that my picture is being taken. I really enjoyed the conversations during and after the event as folks were genuinely interested in UX writing, not just content strategy.

Cate and Shane (one of the Meetup organizers) prepared some excellent questions. There were also great ad-hoc questions from the audience. I tried to stick to my guns of only answering questions I felt like I could really answer, and saying “I don’t know” for the rest, but I did feel a pressure I haven’t really felt before to be the expert. I don’t think this was a good instinct, necessarily, but I did feel liberated to speak with a bit more passion and conviction than maybe I have in the past. If people don’t like my answers they can yell at me on Twitter! I know I turned around at least one question about content testing that I don’t have as much experience with to the audience.

Ten times more

On Back to Work, Merlin has talked several times about the “ten times more” metric. The gist is: look at something in your life and ask if you’d want ten times more of that. For instance, I had a bit of fun buying and selling vintage clothing at pop-up markets and filling orders on Etsy, but not so much fun that I wanted ten times more of it. Realizing that made me it easier to let go of when it became too much.

So that’s what I’m chewing on now, after an event like this. Do I want ten times more writing books, going to meetups, talking to people who care about this stuff as much as I do? I’m leaning towards yes.

Extremely grateful to Cate, everyone else at Solstice whose names I’ve already forgotten (sorry!), Shane and the Chicago UX Book Club, and everyone who came out. Let’s do it again sometime!

Digital junk drawers

There’s a joke that having a writing deadline is the best way to get your house clean. Personally, I channeled this form of productive procrastination into digital spaces while getting to a finished first draft of the book. This was also partly out of thoroughness and desperation — “I know I’ve thought thoughts about this before, did I write it down? WHY DIDN’T I WRITE IT DOWN?”

During this procrastinatory polishing, I cleaned out and killed:

  • An old Scrivener project for the book that I started before the contract was official
  • An old GitHub repository for the book I never really made use of
  • Various text drafts in orphaned folders from when I imagined tackling a similar topic as a self-released iBook in 2014
  • My entire personal Evernote archive
  • nvAlt and thousands of associated text files
  • A work-specific journal in Day One with a few hundred entries
  • Several misc. folders of app screenshots
  • Dozens of mindmaps that had built up in iCloud that I thought for sure I’d need again but were all junk
  • Thousands of junk bookmarks in Pinboard from some social media automation I set up back in the day
  • Two underused IFTTT accounts
  • Six or so novelty Twitter accounts I’d never updated after the first month
  • And lots of other things I’ve already forgotten about

I also processed through a dozen or so analog notepads and small paper notebooks.

Most of this stuff was garbage. Just noise. With ever-bigger hard drives and near infinite cloud storage, our digital closets can be as big as we want them to be. But I’ve found that that’s not without a psychic cost. I felt like I was trying to do my work inside of a giant junk drawer. The elegant chamfered aluminum edges of a closed MacBook Pro can bely just how untidy things really are within.

Cleaning out my digital workshop out in this way helped me feel more productive with the tools that I did still have, and allowed me to approach my use of them with a clearer purpose. I actually use Pinboard now, for instance, and it’s become part of my blogging workflow and book marketing workflow. Bear — which I used to replace nvAlt, Evernote, Apple Notes, and an analog notebook of lists — has fewer notes than any one of those collections had previously, and is actually useful to look at now.

Feeling like I had permission to do this was one of the biggest side benefits of writing a book. Having a very specific project, with a signed contract and a due date, eliminated other possibilities (in a good way), which eliminated excuses to hoard digital things, and gave me more actionable clarity on what was still valuable. “Is this going to help me write this book? How about the next one? No? Then it’s gone.”

(Don’t worry — my PUGS PUGS PUGS folder is still growing exponentially.)