I Am a Product of My Own Failure- Guest Post by Douglas Weissman

Writing has rules. I understand rules. I am also someone strongly convinced that rules are meant to be broke. But in order to break the rules, you must know the rules. It took me a long time to learn the rules of writing and many of them, the most common of them, I learned—not by breaking them—but by failing to break them well.

With the rise of AI and everyone (other than writers) convinced chatbots will take writing jobs everywhere, it’s easy to start off by saying…they won’t. They won’t for the same reason I failed at writing for so long. Chatbots are formulaic. Their entire outlook on writing a sentence, a paragraph, a chapter, short story or a novel is based on their ability to paint by numbers; despite what some may believe, current AI is not sentient and instead uses their algorithm to predict the most logical outcome. This means the Butler always does it in a murder mystery, the city-hardened heroine will return to her small hometown to run her family’s snow globe factory in a romantic comedy, and the hero will save the cat in the first five pages of the story in an action story.

I failed because I didn’t follow these rules. I didn’t just not follow them, I tried so hard to avoid them, I couldn’t see the forest through the trees; I tripped over my own two feet. I—insert another cliché here. By avoiding the rules, I fell into the same traps that created these rules in the first place.

Let’s take a look at the rule, “Never start a story with a character waking up.”

I hated this rule. I would think, my story will be different. I would sit down and start with the character waking up just to show them (whoever they are), it could work in a story. And you know what? It could—and has—worked in stories before. But it rarely ever does work for reasons I had failed to see at the time. Some stories I have read have started with the character springing awake with their alarm going off and they realize, “I’m late!” Already this throws the reader for a loop. The protagonist set the alarm. Why would they be late if they set the alarm for that time?

The stories I wrote that started with the character waking up failed. Why? Because the majority of the time, the character wakes up means the story is starting too far away from the inciting incident. It means we have to get through the boring morning routine that everyone also takes part in.

No one cares about the protagonist brushing their teeth, unless they brush their teeth with orange juice, but they better have a damn good reason for doing so. No one cares if the protagonist showers in the morning, unless they shower with a swimsuit and a golf club, but they better have a damn good reason for doing so. The point becomes, waking up is the equivalent of sharing your morning routine with the reader. It doesn’t lead to, add to, or build tension.

Let’s take a look at the rule, “Never start a story with dialogue.”

I pushed back on this rule time and time again thinking, “this time it will be different.” It wasn’t. Every time, the voice sounded jilted or too proper. It never sounded like the character and I couldn’t understand why. Until I realized, the reader has no idea who the character is on the first line. The character has no idea who any of the characters are by the first line. They don’t know if the character is speaking sarcastically, lovingly, angrily, and to slip the adverb into the text only cheapens the experience. If the first line is meant to set the tone for the rest of the story, what tone would a line be creating if it said:

“I would love to wait here for you all day,” she said sarcastically.

Beyond not knowing the characters’ personalities in the first line, we also have no sense of time or space. We float in an abyss, hearing a bodiless voice out of space and time until the writer grounds the reader.

Let’s take a look at the rule, “The personal makes it universal.”

When I first started writing, I firmly believed I would make a better connection to readers by offering vague details. This would allow an entry point to every reader, from anywhere. Except, when I generalized, readers couldn’t visualize; they couldn’t experience the story or the characters or the setting. They couldn’t smell the oak tree because I just called it a tree.

They couldn’t hear the Radiohead song playing on the radio for the ninth time in a row because I just said, “the song.” They couldn’t walk down the road shaded by elms while looking into the dimly lit bay window of their ex-lover’s home while traffic light flickered on and off because I didn’t think about the level of detail—nor did I think about which details needed to be included—to make it personal to the character; and by making it personal to the character, it becomes a universal experience.


Let’s take a look at the rule, “Show don’t tell.”

This is a rule that many writers struggle with, so my having issues with this rule from the beginning was less about wanting to break it and more about not understanding it. In the end, it hit a similar note as “the personal makes it universal.” I was so focused on inserting details I thought should be there, I wasn’t paying attention to the details that needed to be there. I wrote the man walked with a limp and went into detail about the man’s walk but I never thought about why the limp mattered to the character or to the story. I wrote the grass is green but people expect the grass to be green, so why is that detail important to the story? I inserted detail after detail thinking that was showing, when really, it was drowning, not showing or telling.

I was drowning the reader in details, not important details, minutia I thought needed to be included to make the word-count more robust. Let me say that again; I wanted to make the word-count more robust. It had little to do with the actual story I was telling. True detail, detail that matters do two things:

  1. They give new knowledge to the reader
  2. They affect the story in some way

If I say the protagonist likes cherry pie, fantastic! That detail is going to come around at another point in the story. If I say the lawn of the protagonist’s home is brown, great! That means we as the reader can intuit something about their homelife. If I say the room smelled of sulfur, good! The sensory details offer a richer reading experience and immerse the reader better and faster than strictly using visual cues.

Each of these rules, and more, I have broken knowingly and unknowingly, in the belief I could make it work and during the writing process I now refer to strictly as a “practice.” Show don’t tell; the personal makes it universal; never start a story with dialogue; never start a story with a character waking up; these demonstrate only a small number of writing rules I failed to follow. Had I learned them–understood them—I may have become a better writer far sooner.

But I am a product of my own failure. That doesn’t mean I have lost and given up. It means I have taken those failures–the rejections from literary magazines, the rejections from agents, the rejections from publishers, the rejections from readers, the rejections from graduate schools—and I learned from them. I used them as catapults to reach the next level of my practice. I found my voice, my technique, my rhythm, and my obsessions. These have all made me a better writer.

Instead of running away from failure. Run towards it and embrace failing better.

Then you too can become a product of your failure.

Grab my book, A Life Between Seconds for only $.99 on March 10!


Leave a Comment

Your email address will not be published. Required fields are marked *