Processing my feelings on maybe, maybe not, winning an essay competition

I AM TERRIFIED. On Saturday and Sunday, I spent ten minutes on Substack. It is now Monday. Supposedly, the winners of the essay competition will be announced today, March 2, and DEAR GOD I hope I did not win. Winning fills me with dread, which is an odd feeling, INDEED. Thankfully, the chances I didn’t win are high; the chances I did, exceedingly low. I think. My boyfriend loved my “essay”, which I personally wouldn’t even call it an essay, but he is biased. The robots I enlisted to help edit also “loved” it.. which is, well. I don’t even know what to say to that.

Substack is a bad place for me. Substack to me like fine whiskey to an alcoholic. Substack is a wondrous place with beautiful writing, and anytime I indulge, even for ten minutes, the result is feeling like shit. I don’t even judge myself for feeling like shit about it anymore, it’s to be expected. It houses beautiful writing, right there on the internet, the people are wonderful, and I am not taking part because as soon as I try to, my comparison and analysis paralysis kicks in and I can not longer do anything I love to do with any sense of joy, lightness, wonder.

It’s always been like this, I’m afraid. As soon as my system detects anything “better than me” in my vicinity, it shuts down. That I am then so filled with dread about literally receiving a prize for “~~being~~ having written the best” is, of course, ironic to no end.

The reason I am so filled with dread about the possibility of winning is, it seems to my conscious mind, at least, that this opens up the then-much-larger-than-now-chances that many more people than currently do will read what I have written not only for the competition, but also otherwise, and THAT makes me sick. Why is it such a horror, the thought of people reading things I previously wrote? I don’t know, to be honest. I’ve just never really been one to be seen in any capacity. While I was still in school, I received a lot of praise. High expectations for almost everything I did. I was overextended and became depressed, burnt out, and my grades plummeted. I was smart, but some teachers now no longer knew, and it was shameful as could be. History, in particular, became the subject I was most ashamed of, because I would have needed to study for the first time, really ever, but I’d never learned how that works.

So, today, either everything changes — or nothing.

Interestingly, I cannot hear any part of me that feels authentic when it comes to this. There are two headless ducks, yacking, and one is terrified of winning and doesn’t want it to happen no matter what, and the other is not that opposed and really quite smug about the possibility of receiving $10,000 and some recognition. Where is the real me? What does she feel about this? There is of course also the possibility that I did not win BUT that they still put me in the book, or might mention me in some other capacity, which also fills me with fear. It is a bit more tolerable, imagining that possibility, but still mortifying.

· · ·

Do you watch Bridgerton? YOU DO??? (How unsurprising) Anyway, have you ever noticed that everyone calls Penelope “Pen” from the very start, even before anyone know that she is the famed lady writer Whistledown? Very clever. Otherwise, that show is a disgrace to writers and brains everywhere. Oh, you watch it “for the plot”? Man, I revile and admire you. I told myself till recently I was watching it for the gorgeous visuals. The costume and set design are really something else, but there comes a point where one simply can no longer stand the inane writing, careless acting, and plot-device-riddled plot. Also, I find myself writing like I’m impersonating someone impersonating 19th century nobility, which, well, IT SIMPLY WILL NOT DO.

· · ·

I wish I hadn’t taken part in this competition. I thought there’s no harm in trying, that the worst that could happen was not winning. I didn’t realize that the worst thing was actually the possibility of winning getting stuck in my brain for months after. I wish I had stuck to my original, boring, autobiographical essay, the insecurity. I wish I had left out the fiery prose and weird sentences. I wish I had kept myself small and uninteresting. I don’t want to be seen, I don’t want to seem interesting. It’s enough that Kiryll finds me interesting. It’s all I ever needed. I don’t want anyone else to see.

Am I really that afraid of being judged by a few people as not good enough? Of perhaps being misunderstood? Is it truly all about expectations? Do I not want people to expect me to write more? The emotional nausea is overwhelming at this point; if I do end up winning, I fear I might spend a week sick to my stomach, literally puking.

Did the essay mention how terrified I am of winning? Did it mention any of the things I was actually trying to understand while writing it? I didn’t end up really processing any of the things I set out to. It’s really not a good essay that way. It says some pretty things but it’s not a good essay. It changes neither itself nor the reader. I cannot have won. It’s impossible they would choose my piece as a winner. The software didn’t grade it very well. My boyfriend loved it but he is biased and he doesn’t read much other creative/essay writing. I did not win.

· · ·

Maybe the fear of winning is the avoidance of accepting, absolutely, the most likely outcome: not winning. Maybe the fear of winning is my mind twisting itself into becoming friends with the possibility that yes, even after so many years of inner work and making myself free of want and expectation and letting myself want but also not... I may not win, my efforts may have been in vain, I am truly not that special.

Which is ironic, because that was what the essay I originally wanted to submit — the one I wrote in longhand — was about. The one I chickened out of submitting in the end because it was too personal. Too insecure. Like whatever the fuck I’m doing now.

So — what if I didn’t win? Then we move on. Then, I’m glad, because something I wrote that I am not particularly proud of will not be the face of my writing forevermore. There is enough to do. We are making an app for MacOS. I have written more funny and joyful copy over the last weeks than ever before, and I’m proud of the work I’m doing NOW. I love it. I want to do more of it. So, if I do not win, that is what happens. I continue, and I get to be satisfied with what I am doing. I don’t need to spend a week puking, horrified that people will read my essay.

What if I do win? I could just... not accept the prize. I could say no, I do not wish to receive this.

How is this my current most pressing problem? That I don’t want to win an essay competition? What the fuck? How do I not have worse things to worry about? I mean, I do. But this seems to blow everything else out of the water, even the objectively bad stuff, i.e. I am going to the dentist for the first time in years to get a filling for the first time in DECADES, but that feels like nothing compared to finding out whether I won or lost. I don’t want to know. I just don’t want to know. Why is finding out so horrible? I don’t want to win. I don’t want to not win. I do want to not win, I don’t want to win. How is this so confusing? Why am I so terrible at accepting any attention for my words and work? Where did this start?

· · ·

A school friend in third grade admonished me for answering “I know” when she complimented a drawing of mine I was hanging up in the hallway with the others. You should say ‘thank you’ when someone compliments your work. It’s arrogant to say ‘I know.’ Well, I was brought up to be polite but I genuinely had no idea about this particular part of social etiquette at the time. From then on, I always made sure to downplay how good I personally1but, in truth, objectively found my work, especially when someone complimented it. I made sure to point out its flaws.

· · ·

I want to puke at the idea of someone handing me a $10,000 prize for something I did. I want to hide in fear because nothing I could ever do can possibly be worth seeing and awarding. A lot of my work I do really like upon putting it out into the world, but this particular piece is.. well, not good. It needed more space. It needed more time. It needed less guardedness and more innocence. It was over too abruptly. I don’t like it. It doesn’t make sense. I couldn’t trust the people awarding me from that moment forth if they did so, because if they chose my piece as a winner, their judgment must not be sound.

I am not a person whose photo should be shown anywhere as “winner”. I don’t look like a winner. I can’t even smile for a photo. I wouldn’t be able to stomach even a video call with the jury. Even if all it was for was for them to congratulate me. I couldn’t do it. I would flake. I am a flake. Not even a snowflake, just a flake.

  1. but, in truth, objectively ↩︎

Last revised May 19, 2026.