Five years ago this week, I submitted to McSweeney’s for the first time. Not surprisingly, I got a polite, form rejection email from Chris—the first of nine rejections until I finally got my first piece accepted almost two years later.

Five years is an interesting landmark in terms of my writing career. By that point, I had already been writing comedy for five years. I had written and directed a few short films, several sketches, a web series, and had just started performing live sketch comedy. I had also just finished writing this sketch, the first of many pieces I wrote for my short-lived satirical news series/website RF News (RIP).   

Now, ten years into my writing career, I’ve hit several major career milestones I wouldn’t have dreamed possible five years ago: I’ve written over fifty pieces for McSweeney’s, and been published eight times in The New Yorker. I also teach satire writing classes at The Second City, and am a headline and features contributor to The Onion.

Yet, as I’ve started working on bigger projects, like writing a book and a pilot, it feels like I’m so far away from where I want to be as a writer. I still struggle with basic elements of storytelling like giving the story stakes, keeping characters consistent, and describing things in ways that sound natural. I also haven’t managed to generate anything even vaguely resembling a steady income from my writing, which is a common but nonetheless stressful aspect of virtually any creative pursuit.

That said, I gave myself a little writing challenge this week. Since my first McSweeney’s submission five years ago was March Madness themed, and since this year’s tournament starts this week, I thought it would be interesting to try writing another March Madness piece five years later, comparing and contrasting the two, and seeing where I’ve improved. 

Below is my first ever McSweeney’s submission:

I Know Sports Are Stupid But I Can't Stop Filling Out March Madness Brackets

Well, folks, it’s that time of year again. The Super Bowl is behind us, baseball season has yet to begin, so it’s time to focus our collective attention on college basketball.

Now, as an intelligent, rational adult, I’m fully aware of the foolishness that is sports fandom. After all, sports are just children’s games played by grown men and women whose biggest accomplishments to date involve putting air-filled objects inside meshes of braided fiber, transporting oblong spheroids across arbitrary distances, and traveling between physical locations in relatively short increments of time. So if sports are so stupid, then why the hell can’t I stop filling out March Madness brackets?

I mean, it’s so obvious to any educated person that sports are just arbitrary displays of physical prowess carried out by anatomical statistical outliers. And, yet, for some goddamn reason, I’ve filled out a total of seventeen NCAA tournament brackets, each taking into account different possible outcomes of a sporting competition that no one in their right mind should care about.

After all, objectively speaking, rooting for five grown men to beat five other grown men at a game invented by a YMCA instructor would be complete and utter lunacy. That being said, I can't help but wonder if Virginia really has a championship caliber defense.

But what am I saying? I’ve never been to Virginia. I don’t even know a single person from Virginia. To cheer for a collection of individuals, representing an academic organization I have absolutely no ties to, in a contest that adds no value whatsoever to the human endeavor, would be the most fruitless of undertakings. However, I keep asking myself, do I really think Virginia will be able to get past Cincinnati and Kentucky, both of which rank in the top 10 for RPI?

Hold on, what am I even talking about? RPI? I can’t even remember what it stands for, let alone how it’s calculated, and yet here I am regurgitating this figure like some kind of expert? And who is keeping track of all of these pointless collections of data? Wouldn’t their time be better spent finding ways to eradicate world hunger or Malaria? Then again, how else would I know that Xavier is a totally overrated number one seed, or that, according to FiveThirtyEight, Butler has the potential to be a Cinderella team this year.

Goddammit, I really need a new hobby. Something that isn’t completely bereft of purpose. I’ve heard the latest season of The Bachelor is worth a watch?

Analysis

So, what do we think? Good? Terrible? Okay? If someone sent me this piece today asking for feedback, here’s what I would say:

First, I think there are some solid jokes here. Poking fun at our irrational obsession with sports definitely has potential as a satirical point of view. There’s the central game of the piece about describing sports in an overly academic way (e.g. “transporting oblong spheroids across arbitrary distances”) as a way to expose how silly it is to get so emotionally invested in what ultimately is just a game. I think that does work on some level.

However, I think there’s a few places where the piece falls short. The biggest problem is that the narrator is a little too self-aware of their own foolishness. The result is that it feels like the audience is being hit over the head with the “sports are stupid” message. 

I also think it’s missing the main character's motivations. The narrator is self-aware that they can’t stop filling out March Madness brackets, but the piece never dives deeper into why they can’t stop filling them out. The piece does touch on some of those mechanics, like how they care too much about stats like RPI and get invested in teams like Virginia that they have no connection to.

But I think it would be interesting to explore what is going through the narrator’s head each time they go to fill out a bracket. Is it like a Dr. Jekyll and Mr. Hyde type of thing? Like the narrator wakes up the next morning after blacking out and finds filled out March Madness brackets strew across the living room floor? Now there’s an angle right there. Maybe that’s not right for this particular premise, but that would be a way to take the “there are two parts of my brain that I can’t reconcile” angle and elevate it to something more absurd.

This piece, at 419 words, is also a little thin for a McSweeney’s monologue. It’s great to get in and get out quickly and trim things down to their most essential, but I think the length of the piece speaks to the fact that the main game runs out of steam pretty quickly. Hence the need to explore things like the narrator’s motivations in more detail.

Finally, if the satirical POV of the piece is that it’s irrational to get so invested in sports, there are so many other ways into that POV besides March Madness that I think could be more relatable. I’m not sure “filling out too many March Madness brackets” is that common of a lived experience for most people, and even if it was, it doesn’t really have broader social implications. There are other ways in which people get too invested in sports that actually do have consequences. Like, for example, how sports betting companies prey on people with gambling addiction, or the ways in which parents get too invested in their kid’s sports games to their child’s detriment. So March Madness feels like a weak way to tackle that topic.

Take Two

Five years later, I went in a slightly different direction than I did back then. And, lo and behold, McSweeney’s published it! Progress!

You can read the piece here.

So what did I do differently this time around? Well, for starters, I moved away from the “sports are irrational” angle, and focused more on office culture surrounding March Madness, specifically office bracket pools. There’s a lot to explore there, but I kept it mostly surface level, with some light jabs about the ways in which coworkers don’t get along, or get too invested in petty things like bragging rights. But I still managed to work in some of the same jokes like the button at the end of the piece about tournament brackets for The Bachelor.

The other thing I did that was central to the piece was connect March Madness to the Ides of March, since I realized they’re around the same time this year and I hadn’t seen anyone try to combine those two ideas (if someone already beat me to this I apologize). Setting March Madness in Roman times, and treating the Roman Senate like a modern-day office, gave me a lot of material to play with and provided some interesting ways to connect the two concepts. A common writing technique for comparing seemingly unrelated topics is to use a T-chart like the one below:

By writing down as many things as I could think of for each topic, I was able to find unexpected connections between March Madness and the Ides of March, and “map” elements of one to the other. Mashing up the assassination of Julius Caesar with March Madness gave the piece an added layer of irony. And while the piece doesn’t necessarily have much of a biting satirical edge, it still manages to poke fun at silly office politics and our cultural obsession with sports without feeling too preachy. So, overall, I’m pretty happy with it!

For me, it was satisfying to see that, five years later, I was able to not only write a stronger piece, but also articulate why the piece I’d written five years earlier wasn’t as strong as my writing now. That’s a skill set I definitely didn’t have back then. So I’m hopeful that, five years from now, I’ll be able to look back at the writing I’m struggling with now, and dissect it with similar clarity.

It was also an important reminder that writing is a lifelong learning exercise where ability improves on the scale of years and decades, not days and weeks, so it’s good to occasionally take a step back and remember just how far you’ve come.

Hey! That seems like a pretty good place to end this story! A satisfying plot arc where the main character learns a valuable lesson? Not bad storytelling. And at this stage of my career, I’ll take it.