Out Over My Skis

I decided to serialize a novel on Substack ... here's what I learned

In the spring of 2017, I felt like I was in the catbird’s seat. Not I, we. Me and my colleagues—oh hell, they were my friends, still are—had developed a new way of delivering training: modular, flexible, like Lego building blocks. But we caught sight of doing something bigger and more audacious: delivering personalized training directly to individuals based on their demonstrated susceptibility to risk. All we had to do was continually surveil worker’s online activity to identify risky behavior, then deliver micro-training based on that behavior. Piece of cake!

So we set out after that goal, my co-workers and I, building out our training delivery system into an online SaaS service that helped our customers meet their specific risk-reduction goals. The analysts dug our stuff, and soon we started pitching private equity investors. The way I saw it, we were about to scale like mad and realize our dreams of developing a behavioral modification system that would revolutionize the way companies got workers up to speed and working efficiently. All we needed to do was prove we could do it, get acquired by some deep-pocketed tech giant and, well, we’d shoot the moon!

Guess what? It didn’t quite work out that way. The road got bumpy, Covid hit, and MediaPRO sold to our biggest rival. (There’s a world of pain and regret stuffed into “the road got bumpy,” but let’s save that for another time.) Long story short, by March of 2021 I kicked myself free of the daily grind and wondered what the hell I’d do next.

For a time I considered writing a book about the coming convergence of big data, surveillance, and behavioral modification, something that connected my unrealized work dreams to emerging changes in tech. It would be non-fiction, of course. Non-fiction was my idiom, after all: I had a PhD in American history, I’d written and edited a bunch of non-fiction books, and I’d served as the voice of my company during our time of greatest growth.

Try as I might, though, my heart wasn’t in writing this story as non-fiction: the parts I had experienced were too painful, and the parts I had wanted to experience never happened. But the “what ifs,” the imaginative recreations … boy, those still excited me. And this led me to try an experiment with fiction on my Substack on March 13 of 2022. You can read it here.

When I wrote that first chapter, I felt like was standing at the top of a towering ski jump, and I launched myself down the ramp and out into the clear, cold air of fiction writing. Ever since then, I’ve been leaning out over my skis, learning as I go. This essay is an attempt to share some of what I learned while I’m still up in the air, wondering whether I can stick the landing.

Picture by IOC/Kishimoto

Wrestling with abstract ideas. The biggest problem I faced in writing this story was how to come to terms with the big hairy questions about surveillance and data and behavioral modification that filled my head. I’d spend a lot of time thinking about the thematic elements of my story on the long walks that often kick off my writing days. I’d ponder how individuals can reclaim the right to self-determination within systems that seek to over-determine them in order to extract profit. I’d compare what my characters were going through with what we are experiencing in our democracy, where we’ve got people who are seeking to undermine our political self-determination in the name of autocratic control. I’d marvel at the way we fall in love with technology and become blind to its unintended consequences, its negative second-order affects. But how the hell do I bring these big, wooly ideas into a story that’s fun to read, with interesting characters and satisfying tension?

Early on, I started to pose these questions to myself in simpler terms, to wonder about these ideas in ways that I could really only render in fiction. What would it have felt like to scale up the modular training system we’d developed at MediaPRO, to turn it into a behavioral modification system of great power? What kind of person could do that work? What if the system got corrupted by a corporate dickhead who just wanted to control people? What if the system’s creator didn’t want to see it corrupted? What if it started to damage the very people she professed to care about?

What I discovered was that I could bring these big thematic issues to ground by embodying them within characters who were trying to live out meaningful lives. I knew I didn’t want to go down some Ayn-Rand-John-Galt-speech kind of path, so I needed to portray characters going about normal lives. A big part of my learning to write fiction has been learning to wrestle abstract thoughts down into characters who feel human and a story that people could care about. Only you can tell me if that has been a success.

Who’s telling this story? I started with a guy named Dan—a stand-in for yours truly—telling the story. Classic first-person narration. That worked for a while, but as I went deeper I found places in the story where Dan simply couldn’t see, like inside the heads of other characters. When I saw this, I thought I was doomed: I’d have to start all over. But then I realized, it’s my world, my rules, and I could just shift the point of view from which I told this story. And so, mid-way through, I began to shift to a third-person omniscient narration, and it totally unlocked parts of the story I couldn’t have accessed any other way. This discovery felt like both a liberation and an immense weight of responsibility: I realized that I made the rules in this fictional world, and it was up to me to ensure that it all made sense.

Shifting narrative control away from Dan and on to other characters was a real eye opener, and it helped unlock a real problem I ran into mid-way through the story. At one point in my writing, I was convinced I was headed for a particular type of ending—one I might have lifted from a sci-fi movie, dark and tumultuous—but I couldn’t figure out how to get there. So I did something that was both bizarre and revelatory: I let my characters lead the way. On my walks, I would instigate conversations between the characters and let those inform what came next. I listened to where they took the story … and in that way I understood where I needed to take the book.

I used to hear writers say things like “My characters take the story where they want” or “I’m not wholly in control,” and I thought to myself, what a crock of shit. But when I surrendered myself to the characters I had created, it opened up a whole new way of seeing my story. This sounds like weird mumbo-jumbo, as if I’m attributing my inspiration to some “muse” or something, but it ultimately comes down to me being open to the learning from and listening to whatever pre- or sub-conscious portion of my brain had conjured up these characters. I’m still chewing on the implications of that insight!

I love writing dialog. One of the biggest surprises for me was the discovery that I really enjoy writing dialog. The conversations that exist in this book echo in my brain still—they feel to me like the real thoughts of characters who have become very vivid for me.

Of course, many of these characters have the voices of “real people.” The characters Stamper, Christopher, and Keith all have the voices and some of the personal attributes of some of my closest friends and family; other characters riff off people I’ve run into over the years. But the fact that these characters “started” as people I know means very little, because the majority of their actions and all of their words are entirely made up. The only connection back to the people that inspired them is the sound of the voices that still linger in my mind as the characters speak to each other. I hear those still.

I love being out over my skis. Again and again as I wrote this story I’d exclaim, to myself and to Sara, “This is hard!,” “I don’t know what I’m doing,” “I’m stuck.” If you popped your head into my office, as often as not you’d find me with my elbows on the table, my forehead cradled in my hands, poring over the next problem I had to solve.

My most common writing pose, recreated for this story.

I am not complaining! I judge the quality of my life by the complexity of the problems I’m trying to solve and these have been deeply interesting and satisfying problems. I love writing and I wouldn’t want to be doing anything else. I finished a first draft about two weeks ago, and the chapters are queued up to publish every other week until April 2, 2023.

Thank you so much for reading. I’d love to hear from you if you’re out over your skis. How do you like it?

Credit: http://www.neosaturn.com/skijumping/landing.html