The 40 Hottest Women In Tech, And My Worst Day Online

I've told this story many times to friends and peers, but I've never tried to write it out before. Many of you already know where I'm going with this from the headline, but if you weren't there or you didn't know me, this edition of On Posting is about the first, and most illustrative time I made a bad post.

We begin at a bleary, sparsely attended Andrew WK show on a hangover-addled weekday during South by Southwest 2013, when an editor at Complex emailed me asking if I could write a story called "The 50 Hottest Women in Tech." I was 21-years old, frequently broke, and I leaned on these Complex assignments to supplement the slim pickings of my collegiate music media career. If you are also a millennial freelance veteran, there is a good chance you've written one too. Who could forget the world-famous Complex slideshow? Hundreds of jpegs sliding horizontally across the screen — each assigned to their own individual webpage — sopping up untold Comscore numbers from languid normies across the country using their lunch break to stare at Air Jordans. I think I had written two slideshows up to that point. There was one called, "The 100 Funniest Craigslist Ads of All Time." Another was "The 50 Weirdest Websites on the Internet," or something like that. I don't know. These are ancient memories at this point, and I'm sure my colleagues in this business can attest to the extraordinary biophysical misery of writing internet lists — losing a little bit of lifeforce with every entry, until you're rendered a Dark Souls-style husk by the time you file. 

But Complex paid $10 a slide in those days, which meant that a journalism undergrad like me could kill themselves for a night by trawling through the Craigslist abyss and arrive in the morning, raccoon-eyed, with an extra grand added to a very chaotic checking account. It is kind of shocking to consider how much richer those slideshow assignments were compared to my other frequent vendors at the time. Vice paid $50 a piece, and the checks typically arrived a year after the stories went up. I wrote $5 blog posts for Prefix Magazine in the deepest pits of desperation during my sophomore year at the University of Texas. The Austin Chronicle refused to pay for coverage that ran digitally and not in the paper, which is a fact I learned long after I had written dozens of different pieces for the website. A sustainable hustle this was not. Freelancers, especially young freelancers, typically keep a few unhappy sausage-making gigs under the covers to prop up their Art — be that the copywriting appointments passed around in whisper networks, the soul-killing transcription grinds offered in Study Hall, or the many stories that we write but choose not to tweet out. Consider it the freelancer iceberg; the $250 New York Times opinion section commission breaches the surface, while the murkier, and much larger checks from, say, that time you wrote sponsored content for Pepsi, linger in the frigid depths, serving as a foundation for everything else you do. There are no strict rules here. You take the jobs that you're willing to stomach and deal with the consequences later. I suppose that is the ugliest truth for why I ended up in the position I did; I really wanted the $500 that The 50 Hottest Women in Tech would soon pay me.

So here's how I talked myself into taking the diciest, most retrograde assignment of my career. For one, this was a slideshow, on Complex. Those were the jellyfish of digital media; aimlessly bobbing around the benthic currents of cyberspace with no personal agency or editorial point of view. If written correctly, the list would permanently barnacalize on the underside of countless Google queries through sinister SEO bewitchments, growing fat on accidental clicks and blasé Maxim-grade horniness til the end of time. The 50 Hottest Women in Tech is a story that should not be published, but should I risk it anyway, it seemed possible that the important folks on Twitter would ignore it.

My other justification is even more clownish in retrospect. The more I thought about the assignment, the more I could smell the faint tang of doom on the horizon, so I wrote back to my editor asking if we could run The 50 Hottest Women in Tech without my byline. Instead it could just be, like, "Complex Staff" or something — you know, one of those noncommittal half-steps media companies use when they have to apologize for being racist but don't want to single out the specific executive who is most guilty. The editor declined that option, and — this is true — asked me to consider the slideshow a "celebration" of the women involved, which is the sort of Lacoste-ass feminist theory you frequently heard in the early 2000s when guys like Bill Simmons were tired of being scolded for lusting over Maria Sharapova. 

Still, I took his words to heart. These lists were usually assigned through an Excel spreadsheet, where the writer-in-question was asked to fill in the text and image that would accompany each slide. In that sense, I could sculpt The 50 Hottest Women in Tech as I saw fit, which is how I devised a tragically galaxy-brained master plan. I resolved to include 50 women selected at random across the tech sector, without any additional commentary or analysis on their looks in the copy. Like, one of the women I had in there was Roberta Williams, the 60-something gaming pioneer who designed King's Quest. That way, I could beat my editor at his own game. It would be The 50 Hottest Women in Tech in name only, and readers everywhere would applaud my clever subversion of the chauvinist Complex hegemony. It was fool-proof, or at least that's the way it seemed at 3am on a Tuesday.

This, I think, was the most thirsty, disaster-capitalist moment of my life, which is really saying something if you work as a freelancer. At 21, I was apparently headstrong enough to believe I could imbue a limp, deep-read social criticism into a shitty article with a dumpster headline as if people were going to be breaking down the syntactic nuances of an article called "The 50 Hottest Women in Tech" like it was fucking Hills Like White Elephants. All while still pocketing the $500 fee! Nobody was going to give me the time of day. It's obvious now, and it should've been profoundly obvious then. "Don't you see how I'm breaking our regressive norms of what it means to be hot?" says the man with his Complex slideshow and his facile advocacy, shortly before getting punched in the face and thrown in a ditch.

Reader, The 50 Hottest Women in Tech did not pass through the internet unnoticed. I filed the copy shortly after receiving the assignment on that fateful, debauched SXSW afternoon, and it hit the internet a few days later. The Complex oligarchy shaved down 10 of those slides — it was now the 40 Hottest Women in Tech — and they plucked off a good handful of my protest choices to feature women more congruent with what the headline promised. Namely, conventionally attractive Tech TV anchors or whatever. (The first slide, if I remember correctly, was now the Hot For Words lady.) 

Not that it mattered. That list didn't have a chance in hell with or without my flimsy attempt to save face. I didn't even realize the piece was live until my mentions tab started flaring up with animus, which as most writers know, is never a good sign. 2013 represented the cresting apex for a bygone era of blogging that sustained itself by roasting other, shittier blogs, so it was only natural that the American media class would go for the jugular when they recognized the very ignorant, very 1998 listicle sticking out of their timeline like a sore thumb. They had me dead to rights. Within an hour, those angry tweets mutated and expanded into a full-blown newscycle — worthy of the daily bloggers that websites used to staff in happier days. Grantland wrote about it. As did Mic, MTV, Jezebel, and the other usual suspects. A reporter at The Atlantic called me, it was wild. I had around 300 followers and was still extremely In College, so this was the first time anyone, of any real magnitude, was reacting to something I published on the internet. Within minutes, I had gone from a complete nobody to the day's villain.

The correct thing to do when you're getting cooked like this is to shut up. There is no sufficient way to stem the tide of a Twitter storyline, but I think you need to live through one to fully understand that lesson. So unfortunately, I tweeted so much during the days that The 40 Hottest Women in Tech was in my life. The first post I made, once the water started to get hot, was a Twitlonger explaining my laughably botched dissension; attempting to absolve myself of the list by laying the blame at the feet of the Complex higher-ups who sabotaged my outrageously inert activism. I kept up that momentum for hours afterwards, heedlessly educating everyone who tagged me with my side of the story. Eventually, The Daily Beast — eager to drift in the many hate-clicks showering my bad post with another bad post — reached out and asked me to write a piece about the incident for their editorial. I said yes, offering 800 words to further distance myself from the slideshow by revealing the original 50-women version, like a ghastly ouroboros of media cynicism. We never talked about a rate, and I still feel kind of dumb about that.

This instinct, the idea that your singular Twitter account is capable of out-shouting and out-reasoning the millions of others calling you a jackass, is now defined by the verb, "To tweet through it." But 2013 was a few years before Twitter slang permanently carbonized in our language, I didn't have a code of ethics to cite. So I kept posting and posting and posting, shoveling away at the voices in my mentions with the blunt force of apologia, surprised to find myself trapped more firmly within a hellish parasocial dependency with those I had dragged down with me. The exit was in front of me the whole time: All I had to do was turn off my phone and accept that I was going to feel bad for a while. That is always an option. They really need to teach the art of logging off in J-school. 

The morning after the story went out, I remember navigating to the Twitter profiles of some writers I admired. I scrolled through their tweets to see if they weighed in on The Discourse — the 40 Hottest Women in Tech, the idiot who wrote it, and the hapless way he tried to explain his actions — and invariably I'd either confront a gut-piercing wave of anxiety, or a rejuvenating spark of relief, once I discovered if I still had a chance to make a first impression or not. That was probably my personal rock bottom throughout the ordeal. I remember that Mark Richardson, then the Managing Editor at Pitchfork and a titanic figure in music media, wrote an essay-length subtweet on his Tumblr about, basically, why it's important to take your bad posts on the chin. I grew up loving and idolizing Pitchfork, and yet, my first time crossing paths with the boss was through his own post-mortem on the worst thing that's ever held my byline. Some writers blaze through the gates of superstardom with an indelible, star-making masterwork, and some write the 40 Hottest Women in Tech. 

There were times, deep in the sickness that followed the slideshow, where I felt like I had burnt every bridge in the business in a single afternoon. Never again would I write a professional word. Instead, I'd be condemned to wander the wastelands, occasionally responding to the many furtive eggs forever roasting me in my mentions. It takes a very troubling kind of neurosis to believe that you've destroyed your career at 21, but media labor is rarely kind to its young. 

Of course, eventually the storyline relented. The fever broke three days after the slideshow was published, as the numbers in my notifications tab dwindled to a small trickle. The world moved on to the next bad post, as it always tends to do. I was reinstated into my previous status as an anonymous blogger — a title I used to resent, before The 40 Hottest Women in Tech made me understand how good I had it. The Google results for my name remained splattered with the residual carnage from 2013 long afterwards, but that too eroded away over time as I continued to write for a living. Today, the list is only brought up to me in good faith from people I love. (My girlfriend sought out a particularly brutal takedown from Gawker during our first date together. She read it as both of us sat side-by-side in a too-bright restaurant bar.) I never did hear from Complex again, though I did try to pitch a different editor at the site in 2015. They initially accepted it, before later killing the piece after unearthing my "previous history" with the company. The slideshow itself doesn't even exist on the internet anymore. Currently, it redirects to, "The 50 Hottest Smart Girls in History." There is no byline attached.

Still, I'd be lying if I said that I don't hang onto some latent trauma from the Slideshow Incident — and I say that with the full understanding of how corny it is to associate a term as loaded as "trauma" with mean tweets. But The 40 Hottest Women in Tech has become my professional true north; I never want to go through that again. And so, I've become fanatically stringent with everything I write. I break down every sentence from every possible angle until the words become warped and unintelligible, hedging the arguments and softening the edges to appease any oblique, unaccounted insensitivity or misinterpretation. I quadruple check quotes, and agonize over shifting a clause to make someone's verbiage more legible. What if they sue? I am at my absolute biological worst in the minutes before a story goes up, when the ignition is flipped and I know I can no longer throw my body in front of a draft. I tweet the link, brace for impact, and enjoy the lilting float back down into nothingness: some mild praise and a handful of retweets. Just another day at the office.

I can't say for sure if those obsessive intuitions were strictly birthed out of my 40 Hottest Women in Tech experience. Maybe they were honed by the more general ennui of being a media professional; it's hard to make a living in this business without developing a nose for bad posts. In general though, I tend to believe that the lifelong spiritual injury from a really bad day online can be instructional. There are probably better, kinder ways to learn that it's never worth putting your name on a putrid assignment, but a day or two in the Twitter abyss is a good way to ensure that you will never do so again. We all have our own incarnation of The 40 Hottest Women in Tech that haunts us whenever we open a fresh Google Doc. We've each had our number called. The curse it leaves with us — the voice in your head who believes that you're constantly on the knife edge of calamity — is certainly burdensome, but I think it's also made us into sharper writers. Does that justify how much it sucks when you're in the thick of it? Could we stand to be a little kinder to one another? Who knows, but I'm living proof that there's life after roasting. Odds are, you are too.

Republished with permission by the author. You can see Winkie's original post here or read his previous piece about David Leavitt and the seduction of bad posts.

Photo credit: The Atlantic.