How I’ve Failed At Writing

(And why I keep going.)

Update: This post and the handy guide, How To Fail As A Writer is being turned into a book. If this is something you’re interested in, go here.

It took me a while to write a novel.

I don’t even mean a published one; I mean to write a draft at all.

In high school, I’d write a short story and then tweak and refine it over and over. When those became too hard, I wrote poetry because those were shorter.

In college, I didn’t write a draft either — which was a mistake. I thought I would be a journalist and then I only took poetry writing classes — for some reason. I looked down on creative writing at that time, even though I knew deep down that’s what I’d rather be doing.

But I still didn’t write fiction. Instead, I put it off, and I became frustrated and jealous. Frustrated that my own writing wasn’t as good as I wanted it to be and jealous of those who at least tried to put pen to paper (or saving sentences in a Word doc…).

Problem #1: I wanted to be epic from the outset.

I wanted my writing to be on par with all the great novelists I’d read my whole life like F. Scott Fitzgerald or David Foster Wallace or Flannery O’Connor. But that’s impossible to do especially with the first draft on the first attempt.

What I didn’t connect at the time was those people had failed and failed many times. As readers, we just didn’t see it. They had bad drafts that they threw away. What they delivered to us was perfection from some of the most talented writers the world had ever seen. That’s what I was comparing myself to. Which was horrible, wrong and misguided. I wanted to create a masterpiece from the beginning without any practice, patience or perseverance. That’s how I failed.

Problem #2: I didn’t give myself permission to start.

I wouldn’t even write for myself. I got stuck in research. I convinced myself I had to write a novel with a very full and complex plot. So I read more random books as “research” and delayed it even longer.

Once I did get going — I won’t lie to you — it was still a disaster. I was completely consumed with doing something way different than anyone else. But it was unreadable.

Problem #3: I made it too hard.

What did I do to make it a disaster?

My goal was to be experimental. I created alternating timelines between flashbacks and present day without any way to tell the difference between the two except with minor cues. I also had small breakout boxes of texts that unnecessarily gave the history of a word just for fun — like I had a three-page note on the meaning of the word “gazebo.” Who wants to read that? Then I had just pages of straight dialogue with no set-up, like a screenplay. Like I said — a disaster.

Instead of just writing a story with any normal plot at all as a minimum viable product of sorts, I tried to do the hardest thing imaginable, with impossible goals of being great from the word “go.”


The thing is — I think there’s a nugget of possibility in that story.The plot was about a guy who runs away from a wedding, and the best man is there for the bride’s rebound — but still it didn’t need all of my experimental extras. I lost the story. And that’s really what people care about. They don’t want all the random bells and whistles for show. They want those bells and whistles to have a purpose. They want the attention to craft to pay off.

People don’t necessarily want “grand” either. That’s egotistical. People want fun. They want enlightening. They want clarity. They want meaningful. Now, that’s how I’m trying to write.

This piece originally appeared at

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To help you fail like me, I’ve put together this handy guide, How To Fail As A Writer.

Check it out and then tell me how you’ve failed, too.