What’s been really scary and really hard while writing the first draft

This is a list of things that I found unpleasant as I was writing the first draft of my first book. Maybe you’ll find it interesting; maybe you’ll recognize things similar to what you go through in your own creative endeavours. I would love to hear from you if it did. Writing all this down has already helped me.

1. Feeling overwhelmed

And in two different ways, at least.

The first was just the immense scope of the project. The first day I saw my book as a hollow scaffolding of forty-something chapters made me incredibly happy — this was the day the book became real in the first of many different ways — but it also filled my eyes with tears. It wasn’t just that this was a monumental task… it was also that for half of these chapters I only had the faintest idea of what I’d write about.

The second way was juggling everything necessary to keep the project going. What surprised me was how little writing the book was the actual act of writing. Just keeping my database up to date and filing things in the right pockets took an astonishing amount of effort — let alone following up with people, planning future interviews, reading new things, answering to tweets and emails, and so on.

What did I do to help myself:

• I celebrated accomplishments. Every finished chapter was a bit of a routine where I’d replace the sticky note on the wall, summarize the writing, etc. (Towards the end, I even made it public with [much-hated] selfies.) Every time I achieved Inbox Zero in my database, or processed all the browser tabs, I made a little happy dance. And I talked about bigger milestones just to recognize they happened.
• I have many wonderful friends who supported me in all this, but I also made an effort to seek out support; this was something that has been something historically difficult for me.
• I kept reminding myself this was a hard project, and it was okay to fail — as long as I was enjoying the process and learning from it, I would always remain ahead. (I still feel the same today; even though I’m pretty certain the book is going to come out, I feel like I already achieved a lot that can’t be taken away from me.)
• I clearly partitioned my calendar. Writing days were just for writing: no interruptions, no lunch plans. But there were also preparation days (planning the structure of the next chapter), research days, and rest days.

A typical research day. Each line is not just a browser tab — it’s a *window*, with many tabs open.

2. Feeling insecure about my writing

That’s sort of the obvious one: Am I good enough writer? It took many years to cross the threshold of feeling ready, when my English got to the point my Polish was decades ago. That feeling, however, doesn’t automatically allay all the fears, and it’s really funny to approach a book feeling pretty certain I could handle its typesetting, but much less so that I could handle what’s actually being typeset.

Writing en masse highlighted many of my bad writing patterns. (It was a bit like putting on a macro lens; one thing I noticed, for example, how often I used the word “simply” as a crutch.)

And then, so often I’d read someone else’s writing during that time, and notice how much better they are with putting together wonderful turns of phrase, or making smarter connections.

It’s very easy for all this to get to me, but this is how I tried to help with this part:

• I remember inviting a group of (good) photographers to the Computer History Museum to take photos of machines — something that I’ve done time and again, and enjoyed immensely. I always felt insecure about taking photos of inanimate objects, looking at it only as a stepping stone to taking photos of people. However, after the excursion, one of the people I admired came up to me and said this was really hard and I had no idea what to do! What I dismissed as a preamble was a rare skill of its own. And so, I am trying to embrace that I have a certain “fingerprint” as a writer: I am good at some things (putting a story together, explaining things, emotions, excitement, depth of research), but I don’t have to be good at everything. No one is. I can leave world-building to Stanisław Lem, endings to William Langewiesche, emotional depth to Helen Macdonald. There’ll still be plenty enough for me.
• Keep reminding myself that impostor syndrome is a real thing.
• Listen — really listen — when people tell me they like my writing.
• Trust that half the miracle happens in the editing process.
• Accepting that “the only way out is through”; that I can’t think my way through this, or spend more years preparing. That at some point you write a book, and during that you learn how to write a book. (And hope that by the time you’re done someone invents a time machine.)

3. Feeling worried about the shape and length of the book

My first draft has 317,000 words. It’s a lot of words. I jokingly compared my book to War and peace and The infinite jest, but the truth of the matter is that this is a really, really scary number. On a dark day, it becomes either of these two options:

• You will have to cut out a lot from the first draft, much more than usually necessary. This will be hard because they’re all interconnected, plus you spent months writing all this!
• It will be a lengthy, boring book. Even if it’s not boring, it will be long… and who reads long books? People admire The infinite jest or The power broker, but do you know anyone who actually read either?

A few more scary things that haunt me, at times. One: I decided to write this book out of order. Instead of planning carefully all the chapters, agreeing with someone (or a publisher) on them, and then simply executing, I allowed this book to figure itself out as I was writing. Its eventual length and shape was a bit of a surprise. Two: There is not one book that I know of that is quite like mine. This is really scary. Three: I carved much more time out of my life and career for this than I expected. But:

• Something tells me it’ll be okay, in the end. I want to find a great editor to help me figure it out, and figure out the relationship between the length of the book, the audience, the publishing options, and so on.
• If there’s no book quite like mine, it’s scary, but it could also be a fun opportunity to make something unique.
• If I ever write another book, I will have this experience behind my belt, and know how to do it better.
• Every passing day after having finished the first draft will make it easier to look at the book more dispassionately. Right now, the weight of months spending at my white keyboard feels acute — but it will go away.
• Perhaps this book will be two volumes, which could be an amazing opportunity to do something with its visuals. (First volume themed after typewriters, the second after computers?)

4. Feeling worried about the book’s place in the universe

Is writing a tech book in 2017 and 2018 a good use of my time? Of anyone’s time? The world of tech lost a lot of its luster. The world as a whole needs a lot of non-tech help.

What makes this more palatable:

• This is not just a tech book; I’m trying to focus a lot on people within it and while I might not be fully successful… I can only get better at it by trying to do it the best I can.
• I will frame it like this for people who’ll be reviewing and editing the book, too, to find a better balance.
• I’m good at some things. I’m not good at other things. The best I can do is to try to use the things I’m good at, while making an effort towards the things I wish I was.
• Tech is not going anywhere.
• I try to spend a significant chunk of my time trying to straighten the world — by whatever fraction of a degree I can — outside of this project.

5. Not having a job

I quit my job to write full time. This felt like a hugely irresponsible thing to do, especially for an immigrant. I’ve always had a job; I remember in high school when a teacher made a joke about us not having to pay taxes, and I shouted — with pride, I believe — that they were wrong! You see, I have already been paying taxes then.

Not only I’ve always had a job; during transition points I always knew what was coming next. This time, it’s neither of these two. As much as I could say and believe this side project would come back to enrich my “real” career (I’m not really assuming I will become a full-time book writer!), it’s something it was decidedly outside of it. What helped:

• Seeing a few of my friends do this before I do, particularly friends who worked in the tech industry (ergo people like me, rather than people I considered “artists” who seemed to exist in their own universe).
• Talking to my financial advisor about the realities of all this; actually, switching to a new financial advisor in order to have conversations like this.
• My last job becoming more awful by the day; it made it easier for me to consider an alternative, and I already had this alternative handy.
• I approached it all in bits and pieces; this was accidental, but incredibly helpful. Instead of saying “I’ll spend a year writing” — a daunting prospect — I said “I’ll take a three-month sabbatical.” Quitting was easier after that. Then I kept extending my unemployment, three months at a time. (Itself a terrifying part, don’t get me wrong!)
• The belief that the fear itself will be a good experience for me. That I’ll likely survive all this, and this will make it easier to do more scary things in the future (as a matter of fact, it already opened me up to consider freelancing instead of full-time work).

6. Feeling inadequate as a historian

No one taught me how to research the past, and one of the biggest fears is that I won’t do the subject matter justice. That I will fail as a historian, succumbing to some cheap rhetorical device, or perpetuating a damaging myth.

As I’m reading more and more, it becomes obvious that we’re all seeing a snippet of history. That there are multiple people, inventions, and events left behind. That “first” is a construct: there is never one first, and the politics of a particular “first” becoming the most well-known one is itself the most fascinating subject.

A specific thing I’m acutely aware of is also the absence of women and people of colour in most of documented keyboard history. I can highlight the few I learned of, but how can I do more? How much of it would be enough?

It’s the same with all of the research. How many books should I read, how many people talk to, how many keyboards to look at before it will be enough?

How am I trying to solve this:

• I am planning to do a serious editing process with editors, matter experts, and just great writers.
• I’ll talk (and already have talked) to professional historians about some particular questions and worries I have.
• I should also feel comfortable failing! I want this book to be good — great, even — but it won’t be perfect. I can learn a lot before finishing it, but I will also learn a lot after it gets out and see people’s reactions to it (and criticism of it).
• I’m openly sharing my database and bibliography even before finishing, so that other people can inspect them and offer their own takes.
• For each chapter I wrote, I have an idea who’s a subject matter expert in that area, and hopefully I can convince them to read my draft and point out anything that doesn’t seem right. (Or even feels suspicious.)
• I’m planning to hire a fact checker for at least the most crucial chapters.

7. Worrying about disappointing the readers

I asked people what they’d like to find in the book, and I know a bunch of things they asked about won’t be there, and a bunch of questions they wanted answers to might not be answered. That’s scary — a bit at least — in the sense that I don’t want my book to be disappointing. But:

• I have to trust my raconteur instincts to recognize what the best stories are.
• It’s possible to talk about things that don’t have clear answers or conclusions in a way that’s as satisfying as anything else.
• Of course my book will disappoint someone. It’s impossible for it not to. My book will be opinionated within and without, and I’m making an effort to talk early and candidly about its true audience. (And be comfortable with people who aren’t it.)

8. Worrying about the title

The temporary title Shift happens has been around for a while now, and I wonder how likely it is that it will stay there until the very end. In some way, it’s perfect: catchy, and with a deeper meaning underneath. (The history of keyboards really is Shift happening, over and over again.) But on a worse day, it feels cheap and vulgar.

The title exemplifies a worry about finding the good tone for the book. I like academic books because their authors often put an incredible amount of effort in digging things out — but most of them are really unpleasant to read. (And if academic books are hard, don’t get me started on papers; I’ve seen so many that were fascinating, but also managed to bury all of their amazing value under clumsy, lengthy, impenetrable prose.)

On the other hand, there are catchy books about typewriters that are just cheap, throwaway collections of rudimentary nostalgia mixed with surface-level trivia. They’re fun to read, but that fun never goes anywhere.

I hope I can find the right tone that’s accessible, but not shallow; entertaining, but not forgettable. This is where I hope the editor(s) and the proofreaders help out, and as for the title? It’s probably best to leave it until the end. (And there is, of course, the publishing scenario that takes away my control over the title, although that comes with its own set of worries.)

9. Being awful at interviewing

Interviewing people is really hard. It takes time. It takes a lot out of me. It also takes a certain set of skills that I don’t have. (I’m naturally curious, but I don’t know how to interrupt people, how to think on the spot, or how to juggle hearing what they said with thinking of what to ask next.) Even figuring out some seemingly basic things as Skype recording was surprisingly tricky.

Finding people to interview has been a mystery. Many people don’t know they have interesting things to share, so they won’t come forward. Often, I know a company at a certain time, but all the employees there remain nameless to the outside — and even if know the names, finding people and convincing them to talk to me is really hard. Somewhere in the back of my head there’s a fear that there are a few people who’d completely make my book better if only I reached out to them and asked the right questions… but I’ll never even know they exist.

How am I trying to solve it:

• Just do more of it, accepting that I am bad, will get better, but will likely never be great at it.
• I read The art of the interview book. It was helpful!
• Share my worries — literally right now — just so maybe you can tell me how to get better.
• Celebrate a good interview, like the one I talked about in my first newsletter, and just don’t worry too much when things go wrong (as they did during that same interview in a way that still makes my face red in shame when I think of it).

10. Hating the drudgery of retyping

A lot of my research library is digital, but I also surround myself with hundreds of books. I decided I wanted all the relevant passages from all the relevant books typed into my database for easier access, but that meant that at some point I had to spent a solid workweek retyping things.

This was probably the least fun week of them all. In that one long session, I ended up keying in 85K words — which itself is a length of a regular book! — and added tens of thousands more in the months since.

However! This was perhaps the first time where I found myself being a professional typist and first time where I actually needed to use a better keyboard (my friend’s HHKB), since typing 10K words a day on my regular laptop keyboard started hurting my fingers.

Thoughts about this:

• Maybe next time, I could pay someone to do this for me?
• Or at least anticipate it better and allocate more time for it.
• Also, it worked. It really did. Today, I can type “selectric” or “touch typing” in my database, and it returns everything relevant from the pile of books next to me, without me having to sift through it every single time.

11. Dealing with loneliness

I was stuck in two strange worlds occupied by me and me alone: one of writing, another one of keyboards. Sometimes, those worlds would be beautiful and give me a lot of joy; but at other times, they felt really lonely.

I sort of expected that, and here’s what helped:

• I talked a lot about this on Twitter. A lot. About the process, about the findings, about some of the frustrations. This was really scary: should I be talking about this at all before it’s done? isn’t that bad luck? won’t I spoil fun? won’t I raise stakes? It could’ve become (and was, at times) distracting. It could’ve rewired my brain too much to depend on little everyday doses of dopamine (likes, retweets), and forever abandon the marathon for a series of sprints. Ultimately, however, I think I found a balance and made it a net positive, a nice background feeling of a group of people being on my side.
• I also talked to other writers and creative people who’ve been through this before. All of my experiences are filtered through my specific book and my specific personality, but they’re generally universal. (And that’s why I want to share my process, too, to give some feedback to whomever is next in line.)

12. Untangling the world of publishing

The publishing world is scary and weird. It’s also really complicated. Some people know the traditional way really well — that world of agents and publishers that feels very old because it is very old. But others swear by self-publishing/Kickstarter. Few arrive experienced with the entire spectrum, and yet most have a strong opinion or agenda about my place on it.

The publishing world is also changing, quickly. Yesterday, self-publishing was for losers who couldn’t get a contract. Today, self-publishing is for losers except when it’s not: so many books benefited greatly from going that way. (Here’s one example.) But even then it’s also not universally better than traditional publishing. It’s just different. Each option has pros and cons.

I’ve had many conversations with many people, and I’m only slowly starting to piece together the world of publishing. But I still don’t know much of what’s next, and it’s a bit petrifying; I expected to be much further ahead.

What I’m trying to do to ameliorate my fears:

• Before writing a single word, I wrote down all the things I wanted my book to be. This was a guiding set of principles of what mattered to me; I can imagine changing my mind on some of those, but as they are, they ensure I’m not flying rudderless.
• Just like I did in a bunch of hairy situations, I started writing summaries of my thoughts about the publishing industry, and sent it to more experienced people for commentary.
• I have a bunch of amazing friends who have been in publishing before, and are helping me out.

13. Wondering whether I should be in the book

I inserted myself in a book a bunch of times, although I’m not sure if this is a good idea: does it add to the reading experience, or is it just my ego?

Fortunately, this is relatively easy to solve: if I hear enough (from editors, proofreaders) that I shouldn’t be in the book, I will remove myself from it and rewrite those portions to be neutral.

14. Worrying I don’t know quite yet what’s next

I still can’t tell you when the book is coming out, or even exactly what the next steps are. I think that’s okay. One thing at a time, right…?

This was a list of scary stuff. But there’s also a list of good things that happened. Read more about the Shift Happens book, or stay in touch: