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When Winning Feels Like Losing

May the odds be never in your inbox

By Anastasia BasilPublished 2 years ago Updated 2 years ago 4 min read
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Photo illustration by artist, Pawel Kuczynski

On September 30th, A "Potential Winner" affidavit appeared in my inbox from Medium. My heart stalled.

We ask that you please keep the receipt of this email and the following information confidential until October 15, 2021.

We are writing to inform you that you’re a winner of the Medium Writers Challenge Contest.

I told no one about the affidavit. For two weeks I lived in suspension, balanced midway on a high-wire. Behind me were my daughters, sinking bank balance, and rent was due. Ahead, ten thousand potential dollars.

I don't believe in gods, and I don't believe in an uppercase Universe—one with ears for affirmations and arms that deliver the desires of those who ask correctly. I believe in people; we are each other's saviors. And I believe in work.

So I did not pray. I did not chant, smudge with sage, think positively, wear crystals, align my chakras, steer clear of negative Nancys and Debbie downers. I worked. This old engine has powered through fast food, retail, hair salon receptionist, admin, facilities manager, acting on TV, small parts in movies, voice-over for video games, dog-sitting, teaching camp kids, copyediting, content writing, mommying. While I worked, I tried not to hope. Hope is not fun for those like me. If you relate, we are kindred spirits. I'll take an oil change and a free coffee over champagne with the right people who might make something happen for me. I don't fit there. I'm your common lawn weed—a dandelion or thistle. We don't hope to be other than what we are, we just keep on thistlin'.

A fancy NY literary agent contacted me after reading one of my essays. She wanted to know where I came from. Chicago, I said. "No-no. I mean what writing program. Why haven't I heard of you?" I told her I'd never taken a writing class.

Maybe she was looking for a pedigree, something East-Coasty—a brand she could trust. She asked why I hadn't written for a more visible publication. I felt pretty visible. Medium's backend analytics show that a few of my pieces have over a million readers. This failed to impress her. I had no names to drop but imagined my work (which first drew her to me) might pinch-hit for fancy credentials. She lost interest.

So yeah. Just keep on thistlin'.

I've entered contests before and lost. I wasn't hoping to win this one... until the affidavit arrived. The vague-idavit, as I've taken to calling it. With it, came two weeks of agony. Had other writers been asked to sign a secret legal contract to accept their potential winnings? If so, how many others? One? Four? Ten? Certainly not more than ten. Did I now have a one in ten chance of winning? Careful, mama. There's no net. Stay calm. Thin wire. Long fall.

Did I win? Yes and no. I won $100 and an Honorable Mention. I wept at the news, and this made it worse. It wasn't like me. I come from a long line of... well, losers. My father tried and failed horribly at the American Dream. We were poor. I was raised to take it on the chin. But this experience—this contest, undid something. Vital bolts stripped tight were loosened and lost. I spent days trying to repair myself.

Medium could have sent the affidavit with a description saying which prize my essay was poised to potentially win: 10k category, 50k grand prize, $100 honorable mention. Even better: Don't send a secret, vague affidavit to potential winners. Wait until the winners are publicly announced and then send the winners their affidavits. Winning should be a surprise, a delight, not a two-week psychological mind-fuck. I imagine I'm not the only one crushed by these weird Hunger Games. There were 100 Honorable Mentions. That's 100 "Keep this secret. You’re a winner of The Medium Writers Challenge!" emails. (Reminds me of Hamlet when he said, I must be cruel only to be kind. Medium has to stab you a bit before they award you a hundred bucks.)

Wording matters. How about: "You're a winner of a $100 Honorable Mention Prize!" See how easy that is? And what a lovely email that would be to receive.

I write this hoping the contest organizers will tweak a few things for next time. I’ve enjoyed reading many of the winning essays. Congratulations to all. Keep on thistlin’!

For the curious, here is my essay. (It is three minutes long, minus two weeks of purgatory.)

humanity
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About the Creator

Anastasia Basil

My heart belongs to dogs and stories. (Is there a union for introverts? We should organize.) 🖤

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