How failing taught me more than succeeding

Last summer, I enrolled in an Essay/Creative Nonfiction class with Gotham Writers, a New York City online writing school. Half a year later, I can safely say it changed my life. I was a writer before this class: a professional songwriter and a devoted Morning Pages writer. But essays, in my mind, were boring things we wrote in school to get a grade. I was very wrong about that assumption.

Beth Livermore Hersch, the essay teacher, is a prize-winning, widely published journalist, but her pedigree is not what lit me on fire. It was her passion for essay and short story that captivated. It was the way she glowed with respect when she taught us about Joan Didion. The way her hands would fly through the air descriptively when she was lecturing on lyrical essay, and how she would absentmindedly pull on tendrils of her hair when walking us through thoughtful, personal essay. Her laugh boomed through Zoom when she presented a humorous short story, and by the third week, I was a goner.

Essay and short nonfiction had my heart

That class left a creative mark on me. I kept writing and found Medium, which led me to my second impressive writing teacher, Shaunta Grimes and Ninja Writers, an online writing group that offers classes, calls, and writer support. Shaunta and the writing group gave me real-time feedback and taught me how to blog and format my work in a more readable way. Like the essay teacher, Shaunta and the Ninja Writers gave me the nudge of confidence I needed to write stories and post on Medium. I thrived in these classes and groups.

My life flipped on its head in 2020

I’m sure yours did too. A deep need to re-skill, upgrade the tools in my creative toolshed, and reinvent my work kept me up at night. So, in February 2021, when another Gotham class popped into my inbox, I bit the hook.

Hit Send: Publishing Short Nonfiction was the bait

I went into it like I did all previous classes: optimistic, excited, encouraged. The teacher of this class, Lara Ewen, also has an incredible list of publishing accomplishments. She is possibly the most upbeat, positive teacher I have ever experienced.

Her responses to our questions were nearly immediate; she made herself available to us for anything we had trouble with or if we just needed extra insight. Her critiques were spot-on, professional, no-bull, yet so encouraging she made us feel like we could all get published — sooner or later.

The class content did not candy coat the endeavor ahead of us in becoming working writers

If anything, it scared me a little. The opening lecture began with the basics; what does it mean to be a freelance writer? It took us through perks like setting your own hours, being your own boss, sharing spaces or ideas with fellow writers, constantly working on something new, being in contact with many different people while working on articles.

The class taught about finding our niche, creating a “Wheelhouse” and a “Platform.” It let us know there is a voracious market out there for nonfiction and essays. Nearly all magazines and newspapers now have digital subscriptions that need constant new material.

The good news is, there are almost unlimited outlets for nonfiction right now. The bad news is, not all of them pay or pay well. And then there is competition — all of us competing for those slots in publications.

By week three in this four-week class, I felt a knot in the pit of my stomach. We were in deep by this point on challenges and hurdles to getting published. I felt my momentum losing steam, in spite of an engaging teacher and a potent class. There were two words that tripped me up, and all working writers know them well:

Query + hustle

So, in this game, you don’t actually write the articles first, then pitch your carefully crafted work to publications the way I imagined it in my head. The rules of play are this: Constantly have a well of ideas to draw from that you feel confident writing about. Get quick and good at research. Stay up on all the current trends, subjects, and things people are talking about — you’ll want to write about those a lot. Then, when you’ve got that down, master the art of the Query Letter.

It makes sense

You don’t want to spend all that time writing a 2,000-word essay or article only to have it rejected by dozens of editors because it’s not exactly what they are looking for. Instead, you pitch them the idea and why you are the best person on the planet to write this idea. If they bite your hook, then you write the thing. Write it well, and be willing to take the editor’s suggestions and changes. Then, and only then, you might land a paid publication.

I imagine any published writer reading this may think, Yeah, so? No problem. It’s what we do. I salute you. This game takes serious skill, ridiculous passion, and a very thick skin.

The query letter

In week four of this class, our final assignment was due. The same week I landed a part-time job managing social media content for a non-profit, and dove into learning Airtable and another managing App. Yes, it added to my workload, but it wasn’t insurmountable. I used to pride myself in being a good student, always striving for a high grade no matter what was going on in my life. I like a good challenge.

But in the final inning, the final assignment, I bailed on the class. The night before the deadline, I sat down at least six times and tried to hammer it, coax it, convince it, lure it onto the page, and I just couldn’t do it. On the last try, my fingers stopped typing and sat on the keys, unwilling to move. A wave of frustration welled up, with tears burning my eyes.

The blinking cursor just blinked

A voice in my skull asked, “Why?” and suddenly, that word flew out my fingertips and appeared where the cursor had been. I didn’t even realize I typed it. I stared at that word for a few heartbeats as if the cursor would answer me. And it did.

“You’re not ready for this yet.”

Truth can be a buzzkill

My ego was so excited to run out and be a writer after six months of writing essays and short stories that it never occurred to me to let the process cure a bit. I’m a slow writer. The hustle and pace of freelancing intimidates me. So, I succumbed to the voice in my head that said, “You haven’t been writing long enough to slam out an article a day and write well — to make a living as a writer.”

I could have finished the assignment anyway and turned it in. But I didn’t. Instead, I wrote the teacher an email telling her why I bailed. Lara Ewen’s response blew my mind, and I’ve been writing every single day since. Funny how that works.

In terms of freelancing, here’s something to think about. If you don’t need it to be a full-time job for income, then you don’t have to take it at a breakneck pace. Since you’re earning money from other sources, now is a great time to dip your toes in the freelance pool, as it were, and find out what you most want to write about!
Maybe just commit to writing and pitching three stories this year. Really. Just three. If you can start there, then maybe next year, you write and pitch six stories, and the following year, move up to writing and pitching a story every month. Take your time and build the freelance life that works best for you. Don’t let anyone — not me, not a class, not anyone — tell you what freelance writing looks like for you.

THAT, my friends, is the mark of a great teacher.

The most valuable, important thing I learned about freelancing came from bailing on my publishing class.

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Why I Bailed on My Publishing Class