Can you write a full book in a month? Q&A with two aspiring novelists

Founded in July 1999 by writer Chris Baty (who we’re proud to say leads the UX Writing team at Dropbox), NaNoWriMo has been the catalyst for over a dozen bestsellers. This year, Dropbox Paper is sponsoring NaNoWriMo—and that inspired two of our own to take on the challenge. Today, Jenna Crane, Product Marketing Lead for Dropbox Paper, and Ben Taylor, Content Strategist on the Dropbox Global Brand Marketing team, tell us how their creative flow is going on day three of the marathon.

How far into the process are you? 
Jenna: I am a “pantser.” In NaNoWriMo terminology, there are planners and pantsers: people who plan it all out versus people who fly by the seat of their pants. I had an idea I’d been thinking about for a while, and I’m just starting from the beginning and seeing what comes out.

Did you start with a character or a theme or a plot?
Jenna: I started with a “what if” scenario and fleshed out the implications of that. I did the whole first day without having a single character, then I had to decide, “Okay, who is the person in this book going to be?” On day two, I added a character, and I haven’t written yet for day three.

Are you doing an outline or treatment?
Jenna: The background for me is that I haven’t written outside of work in five or six years. For me, this is really the push I need to start writing again. I’m trying not to be too critical and just use it to get into that mindset again. That’s how I’m approaching this: just writing and seeing what comes out. I’m not trying to be too calculated about it.

Ben: One of my guilty pleasures is reading murder mysteries. And I think if you really polled people, there’d be quite a few who’d admit to that. So I’ve read maybe 30 Agatha Christie novels, maybe four Dorothy Sayers mysteries. I recently got into John Dickson Carr, who is a somewhat forgotten, early 1900s American author who’s famous for the “locked room” style of mystery where someone dies within four walls and there’s apparently no way anyone could’ve got in, but the solution is always very scientific and pragmatic. So I set out by trying to envision the solution to a crime. I wanted the actual outcome of the novel. I figured that all out, then I worked backward. What’s the setting? What’s the time period, which was kind of important because of the logistics of the crime. Then I stumbled my way into some characters.

Did you research a crime or base the story on something you’d read in the newspaper?
Ben: Leading up to it, I purposefully read three or four specific books that I heard were pretty good to try to get some inspiration. The Nine Tailors by Dorothy Sayers is very good. I also read The Three Coffins otherwise known as The Hollow Man by John Dickson Carr, which I highly recommend. But I also researched different kinds of poisons, which made me wonder if big brother would come knocking on my door! (laughs) That was basically the research I did. But also, the book is based on a tech company of sorts, so I was able to leverage some personal experience about the nature of a business dinner.

Has it been difficult to shift from business writing to fiction writing?
Jenna: That’s been one of my biggest barriers. For so long, I’ve written in a business context, where I’m trying to be as clear and concise as possible. And I forgot what it’s like to just describe a situation or conversation. It’s a very different muscle. I thought, “Well, I’ve been writing consistently for a decade plus now. I should be able to just switch over to this style of writing.” I got 700 words in and said “Well, there’s the whole plot, so…” (laughs) How do I fill this out and extend it into 50,000 words?”

How would you describe the genre? Is it science fiction?
Jenna: Yeah, a little dystopian and sci-fi-ish.
Ben: Sounds great. When’s it coming out?
Jenna: Never, probably, at this pace! (laughs)

Has your initial idea taken any unexpected turns?
Ben: For this book, because I scoped out the solution in advance, I knew what I was writing toward and that helped. The hardest part for me has been, how do I make it so the heroine can research the crime, have motivation to do so, and stay at least on pace with, or ahead of, the police. And how do you make that realistic?

Jenna: Mine kind of took an unexpected turn in that, in trying to find my character, I ended up putting myself in it, essentially. That’s an easy way to start! (laughs) In doing so, I examined my own motivations for why this idea was exciting to me. It’s about this technological advancement that people are clamoring for, but it has some dark implications. In thinking, “Why is this interesting to me?” I realized it’s because I would totally want that. From there, I thought maybe that’s the way to explore that kind of technology: through someone who wants it, but why?

How much do you feel like you’re steering the story versus discovering it as you write?
Ben: For this book, it’s been more of a steering situation. I could see myself doing NaNoWriMo in the future and being much more of a discovery process. Just hearing Jenna talk about a dystopian future story, that would be really fun. And I’d actually love to write a novel that’s more discovery based, where I just try to write myself into a world like that. But with this one, it’s very mechanical. It’s a puzzle. I have various clues that I lay out as I go. Here and there, a piece will spiral out and I’ll realize I need to go chase after it a bit and get outside of my path for a few hundred words. But largely, it’s been more of a steering process for me on this one.

Jenna: I feel like I’m cheating a little bit because as soon as I started writing about my own experience, the words just flowed out of me. I felt like I was juicing a stone for the first day. I did about 700 words in about an hour. And I did all the calculations: “Oh, no, that means I’ll need to do this many hours per week to get to this.” Then last night, I wrote for half an hour and got 1,100 words. And I thought, “Oh, interesting. Because I’m writing about my own experiences, I don’t have to do too much creative thinking necessarily.” So I’m using that to kind of ease myself into the whole process. One of the biggest surprises is that I thought it was going to be about writing, but it’s not. It’s about ideas and creativity. The writing is just the mechanism through which you explore those things.

How much of yourself would you say you’re putting into either the plot or the characters?
Ben: My wife shares a lot of traits with my heroine. Very observant, quick. Keeps her cards kind of close to her chest, then lets them out at the key moment. That’s made it easier to write her than maybe trying to completely make someone up. It’s been kind of nice because when I’m writing for work, I’ll usually keep editing every sentence as I write it. It’s pretty slow going. And with this, after the first seven minutes, I can usually get going, and I let myself use some adverbs (laughs) and there’s some adjectives floating around. So it’s been freeing to be able to do that and be kind of funny and a little more expressive, even if it’s a little bit wrong or something’s telling me that.

At what point does the work become play?
Jenna: I’ll let you know when that happens! (laughs) That usually happens for me for one of two reasons. One is when I like what’s coming out and I think “Oh, this is fun. I can get behind this.” I’m not at that point right now. I’m like, “Oh, this is crap. I need to go back to reading books and remember how actual people write.” Two is when it’s kind of cathartic, when I’ve written about difficult experiences in my life. That’s when I’ve totally gotten immersed in flow and just realized it’s almost a form of therapy.

Ben: For me, I had the most fun writing when I got to the portion where Scarlett, the heroine, and the detectives end up working together. They’re going over a few of the theories that turn out to be spectacularly wrong. What was so fun about it for me… when I get to a certain point when I’m reading a mystery, I get to a point where I like to put the book down for a minute and think about what I think could be going on. And this was my opportunity to write it the way I think about it. And it’s a classic mystery trope where the book will, at least once if not six times, try to trick you into thinking “This is it! This is the answer!” You can’t do it too much. But I really enjoyed that process of being able to write down the ways where I was thinking, “Okay, here’s one way to think about the entire crime.” It’s not what I actually have planned, but to me, it’s a fascinating way to look at this. And I actually get to write all of it. For whatever reason, I’ve always thought it was fun to think through those different approaches.

What tools do you use to capture notes when you’re brainstorming?
Ben: This is not meant to be an intentional plug, but sometimes I’ll pull up a Dropbox Paper doc.

Jenna: I was gonna say “There’s this amazing thing called Dropbox Paper!” That was going to be my answer. (laughs)

Ben: I wrote about 25% of my novel on my phone. This was just before I started at Dropbox about a year ago. Sometimes I’d be on public transportation or at a park and I’d have a moment of inspiration. Honestly, when I’m not doing the kind of writing we were talking about, where I’m editing every single sentence as I write, in which case I do kind of need a computer. But when I’m just kind of letting it go, I’m totally fine for a hour or so, just writing on my phone. It’s weird. I wouldn’t have expected this four years ago, but I’ve just gotten so used to communication on my phone, and apps have gotten so much better that that’s where I’ll do it.

One thing I will do is sketch things out. Even though I’ll mostly keep things digital when I’m writing or taking a note, I did use pen and paper to sketch out the floor plan of the mansion where the dinner took place and a subsequent scene occurs there. Just looking at the spacing and “Would this person have time to walk from this place to this place unnoticed?” That was the kind of thing I’d do when I didn’t have anything else in front of me.

Jenna: I’ve been using one Paper doc for the writing and one for the notes about the writing. I took a screenshot of the placeholder text that came up when I first opened the doc (to begin the project). I thought it was funny because it really conveyed my feelings at that point:

Jenna: Then my meta notes and to-dos have themes that I want to explore and plot ideas. I’m keeping track of my weekly progress. I’m only 14% of where I need to be on week one.

Has the experience of NaNoWriMo changed your approach to brainstorming?
Ben: For me, it really has been the experience of turning off the inner critic. It’s kind of a cliché among writers. I think what’s nice about NaNoWriMo is that there’s so much to write, and comparatively little time to do it, so you’re forced to push through. It took me a good hour the first time I sat down. The inner critic was deleting things and deleting things.

But getting into hour two or hour three—it’s like when you need to lose the hiccups and you finally do, but you don’t realize when it happened—there’s a moment in hour three where you realized, “That inner critic has been off for 90 minutes. How did this ever happen? It’s been a decade since that happened to me. So that was really cool.