How To Author Like a Strategist, Part III: Failing
Welcome back to this letter’s series on being strategic with your projects! Thanks for sticking with me over the last few letters and the break in-between: I decided to revert to a bi-weekly schedule to give myself (and you) more time between letters.
So far in this series, we’ve tackled Planning Meticulously and Executing Immediately. Today, we tackle Failing Swiftly.
Photo description: Me, standing with my bike and staring into the sky, contemplating failures
Once, during my undergrad years, a friend asked me what my biggest fear was, and I said it was failure. At the time, I was petrified by it. I did not want to drop a single grade I did not have to, did not want to make any mistakes. I’d walk around filled to the brim with anxiety, worried that one day I would drop all the glass balls I was holding up and they would all shatter.
Then I became a writer and all that changed.
One of the things you must have in your arsenal if you work on numerous projects the way a writer often does is to be conversant with failure. Notice I didn’t say comfortable, but conversant, meaning that you must understand the role of failure and learn how to use it purposefully. But failure can also mean different things, so let me clarify how we’re using it in this context.
When failure doesn’t really mean failure
Think of all the balls you juggle in life as existing on a spectrum. On one end, you have rubber balls; on the other end, glass balls. When you make a mistake, or something you’ve been working toward fails, and that thing is a glass ball, it shatters. Broken, gone, irreplaceable. On the other hand, if it’s a rubber ball, it bounces back.
Your projects are rubber balls.
Most of us aren’t trained to differentiate between the rubber balls and glass balls in our lives. Many are raised to treat all failures as the same. Erroneously spell a word wrong as a kid (rubber ball) and you get laughed at. This is obviously different from committing an egregious crime, for instance, which could change the whole course of one’s life (glass ball). But if we don’t learn to separate them early on, our emotional responses to those two things are developed similarly, making it difficult to know when to embrace failure and when to eschew it.
But rubber ball failure—henceforth RBF—is an essential learning tool. And when you’re working on projects, this is how you learn. As an author, I sometimes have to begin writing a book in order to discover what won’t work. In other words, I have to first “fail” so I can succeed. Here are some other ways these show up in my projects:
I start a story and get stuck halfway because I suddenly don’t know where it’s going. So I leave it alone for a while (to return when I’m better equipped to tackle it)
I submit a finished story or novel to an editor or publisher, and it gets rejected (which could be a signal that I need to return to the drawing board)
I teach a lecture or assign a writing prompt to my current students, ask them for feedback, then use that to redesign the lecture for forthcoming students (most times, the lecture is almost never at its best the first time)
Learning to differentiate between RBFs and GBFs is a useful trait to imbibe. It is key to boucebackability, and could literally be the difference between giving up on your project or using your failures as a springboard to successfully completing it.
Fail fast, fail often (and other cheesy statements that are, annoyingly, true)
Anyone ever read that book, Fail Fast, Fail Often? I haven’t, but I know at least that part of the title is true (the subtitle, How Losing Can Help You Win, I’m not so sure of). Failure gets a bad rap, but it’s for one reason: failure and time have a contentious relationship.
Stretching our rubber ball metaphor even further, what happens when you drop one but aren’t prepared to catch it when it bounces back up? Well, it runs away from you, is what, and then RBF or not, it becomes true failure. Why wouldn’t I be prepared? you say? Well, because:
you don’t fail often enough to learn to catch the ball when it bounces back; and
you don’t fail quickly enough to be primed and alert for its return.
A lack of failure could breed complacency. Being alert and knowing it could happen—heck engineering failure, even—is the best way to train yourself. And if you do this over and over, soon you become the puppet master, juggling RBFs to do your bidding.
Tips for failing RBF-style
Actually, today I will leave you with a LitHub article from Sarah Labrie, explaining why writing is supposed to be difficult. Mostly, she focuses on the struggle, but I think the lessons lie in the knowledge that it is supposed to happen, it happens to everyone, and that it’s okay. I enjoin you to read the whole thing to glean the points she makes, but I will highlight some of my favourite below:
No one expects a medical student to perform surgery correctly on his first try. And no corporate lawyer would be allowed to negotiate a merger without experience and years of law school behind her. Lawyers and doctors learn by doing. Writers feel we should already know.
Writers aren’t gods alone in a room, pumping out perfectly metered prose from the time they sit down at their desks until it’s time to go down to the bar. Writing is a lot of frustrating, hard work completed over time. Whether you’re good at it or talented winds up mattering less, in the end, than the ability to keep doing it.
