I’ve Done This 500 Times

This is the 500th post I’ve written for Autostraddle. Well, the number’s probably higher than that if we factor in roundtables, group posts, co-authored posts before the website implemented dual bylines. Higher again if we count unfinished drafts, lingering projects. But 500 times, I’ve written a solo piece here that went on to be published. I’ve done this 500 times.

But there are still days when I feel like I’m bad at it.

kayla kumari upadhyaya at age 23 wears a backwards hat and an unbutton baseeball jersey and a black sports bra and black high-waisted pleather leggings

portrait of the writer at 23 years old / when she thought she was futch

On November 10, 2015, I received an email from Riese Bernard telling me I’d been chosen out of 550 applicants to become a writer at Autostraddle. I’d recently moved in with two friends, who were dating at the time, and was sleeping on a cumbersome futon in their living room in a Chicago walkup I still miss, often, even if I never had a room of my own during the seven months I crashed there. I was 23, and I’d only been out to myself and anyone in my life for a little over a year. And yet, in a burst of wild confidence, I decided I was not just a lesbian but that I was going to write about being a lesbian for the internet. I knew next to nothing about my own queerness. I hadn’t even told my family yet that I was gay; that would come three months later. I knew next to nothing about my own queerness, and yet I also already felt it was the bone beneath the flesh of my writing — impossible, or at least extremely fucking difficult — to extract.

Sometimes, I want to take some of the things I wrote back. Things about relationships and friendships and dating and moving through the world that I don’t agree with anymore. I know they’re not lies, that they’re just past truths. But I’m also haunted by the first personal essay I ever wrote for Autostraddle, the one I wrote my ex-boyfriend out of. In fact, this isn’t even the first time I’ve written about that essay — I really should stop writing essays about past essays, but it’s hard not to look back when you spend almost eight years documenting your life on the same website, when you do this 500 times.

Sometimes, with television recaps or reviews, I have no recollection of writing them at all. It’s like reading someone else entirely.

Sometimes, with essays, I feel like I’m just writing the same thing over and over. An essay echo. And then I start to feel like a fraud.

I was going to write something funny for my 500th post. Something like one of my greatest hits from years ago, like Did I Ever Look Straight Once In My Life? or The 25 Gayest Things I Did When I Still Thought I Was Straight or 28 Hats I Wore When I Thought I Was Straight, Ranked from Gay to Gayest. But instead, I’m writing something honest. And the honest truth is that you can do something 500 times and still have moments where you feel like you can’t or that you can’t well or that you’ve been faking it this whole damn time.

I hesitate to say this, because as an editor I’m always trying to help my writers through their own imposter syndrome demons — which, in my opinion, look different for everyone — but I don’t think the bad writing days necessarily get better. They often feel worse. I was, in many ways, more confident about my writing, my queerness, my life in November of 2015 when I was living on a futon and drinking full French presses of coffee at 8 p.m. and, yes, I was a writer then, but it also sometimes felt like I was cosplaying as a writer, grasping at things with feral determination, never sitting still long enough to figure out what it was I was really feeling, what I really wanted to say. It was easier to find confidence when I knew next to nothing. I don’t miss it though. Because even if the bad writing days feel worse now, I also have a better understanding of how to get through them, better tools to carry me through. The problems feel bigger, but their solutions feel more within my grasp.

Practice makes perfect or whatever, but I don’t believe in perfection when it comes to writing. I’ll always be practicing. I’ll always have bad writing days. I’ll always have days when I feel like a bad queer, too. The bone in the flesh, remember?

I’ve done this 500 times. I hope to do it 500 more.

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Kayla Kumari Upadhyaya

Kayla Kumari Upadhyaya is the managing editor of Autostraddle and a lesbian writer of essays, short stories, and pop culture criticism living in Orlando. She is the assistant managing editor of TriQuarterly, and her short stories appear or are forthcoming in McSweeney's Quarterly Concern, Joyland, Catapult, The Offing, and more. Some of her pop culture writing can be found at The A.V. Club, Vulture, The Cut, and others. You can follow her on Twitter or Instagram and learn more about her work on her website.

Kayla has written 914 articles for us.

16 Comments

  1. crying reading this thinking about how you passed that opportunity Riese gave you on to others (including me, obviously). love you so much, dude. so proud of you and the work you do.

  2. If you ever want to think about imposter syndrome, I’m 95% sure that my 500th post was an Also.Also.Also link round up (not that I’m not proud of those! But you know what I mean.)

    Kayla you are one of the best writers, best queers, best people I know. Every day I get to wake up and make magic with you has been a gift. My co-conspirator! Happy 500th. I can’t wait to see 500 more.

  3. “I was, in many ways, more confident about my writing, my queerness, my life in November of 2015 when I was living on a futon and drinking full French presses of coffee at 8 p.m. and, yes, I was a writer then, but it also sometimes felt like I was cosplaying as a writer, grasping at things with feral determination, never sitting still long enough to figure out what it was I was really feeling, what I really wanted to say. It was easier to find confidence when I knew next to nothing.”

    wow yes i relate to this so hard 100x!!!!!

    anyhow here’s to 500 more!

  4. I also hope you do it 500 more times and 500 more beyond that! Thank you for sharing this Kayla and for all the work you do to encourage your fellow writers every day <3 I'm really glad you applied back when you were 23 and that you're still here and I get to work with you!!

  5. I felt every word and every line and every sentence in here. Eternally in awe of your ability to write with such warmth and heart and deep sincerity. Here’s to 500 more, here’s to 5000 more. Thank you for all the work you do, and for sharing so much of your skills with all of us here.

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