🔒 Some News on My Book, and a Requiem For a Career

Next week I’m going to be submitting a 20-page book proposal to a real, living, big-deal literary agent, but it feels like being tagged out as I’m sliding into home base.

 It’s very much not the type of book I thought I would be pitching. I always wanted to write novels. I still do, but I’m getting old and I hear new novels are just being fed directly into Anthropic’s AI training computer/shredding machine as soon as they leave the printer now.

 The book that I actually wound up writing is intrinsically related to all of the reasons that I have to be hopeful, but realistic, about its actual chances of publication. It’s more than just AI and what it might do to the entire writing industry going forward. It’s about how we allowed the internet to become a Trojan horse for a class of reactionary bullies who used it to hijack culture from within, bulldoze social progress, and erect tentpoles of populist fascism all over the Western hemisphere.

 Ambitious, huh?

 Part of the cultural revolution project is erasure. A few months ago I wrote about how the internet is being erased, partly by neglect and partly by malice, but I didn’t realize at the time how imminently this erasure was going to affect me, personally.

If you will indulge me a bit of backstory, I’ll try to get to the point as fast as possible:

 From 2008 to 2019 I worked for the pop culture website Cracked, first as a freelance contributor, then as an editor, a columnist, and a researcher. How I got this job was a miracle of circumstance: Sometime in the 1990s, when I was still in high school, I registered an account on an internet forum attached to a website called David Wong’s Pointless Waste of Time, which was run by a guy named Jason Pargin, who is now a bestselling novelist. Over the years I worked my way up through the ranks as moderator and then administrator, which, if you’re new to Millennial internet lingo, is internet cop and internet Judge Dredd, respectively.

 In 2007, PWOT, as we called it, was purchased by a media conglomerate called Demand Media (apparently now “Leaf Group”) which had also recently purchased the intellectual property of an old Mad Magazine clone/competitor called Cracked Magazine. Their attempt to relaunch a print magazine had failed, but they wanted to lean into digital media, so they hired Pargin as the executive editor of this project. Pargin, in turn, hired people he knew and trusted as contributors and editors, including myself.

 During Pargin’s tenure, Cracked rocketed to one of the internet’s most popular websites, and for a while, in our content category, we were rivaled only by CollegeHumor and something called Funny or Die. The latter, you understand, was run by people like Will Ferrell and Judd Apatow, and we were still regularly trouncing them in pageviews. We felt like the kings of the internet.

 Over a decade of words on the page, looking back, it surprised me how little I had actually published under my own name. The bulk of it, by far, was the editing, which, in most cases, was very much better described as ghostwriting. We were voracious for content—we turned back nobody on the basis of their ability to write. If the draft made sense and was written in English, we could turn it into something we could feature. Hell, we billed ourselves as a comedy website but we didn’t even require jokes in the draft. We could supply those. As long as we had a scaffolding, no matter how flimsy.

 Sometimes I’d get a quality piece I could punch up a little. Sometimes I would write basically the entire piece from scratch. Most of the time it was somewhere in between, but since the quality threshold for incoming drafts was so very low, there was a lot of rewriting, recomposing, restructuring. This was a very good place for amateur and zero-experience writers to get their start.

 I published fewer than 50 articles on Cracked under my own name. I didn’t keep a tally of how many I edited, but the math of it works out to being somewhere between 400-500 articles. Most of those were more than half written by me, and I want to say, maybe, a third or so, were written entirely or nearly entirely by me. These articles were getting millions upon millions of pageviews. Words I had typed were being read daily by a number of people comparable to the population of Barbados.

 In any case, none of the pieces I edited got my name on them. That’s just how it worked, and I imagine it’s pretty standard—whether 1% or 90% of the text was mine, full credit went to the person who had the idea.

 I was paid extremely well for this. I was paid, frankly, better than I actually deserved. But you need to understand the money printer that was Cracked in its golden age.

There were many factors that led to Cracked’s rapid collapse in the years between 2015-2020, but a major one was related to the rise of the tech oligarchy that none of us really realized was happening back in those years.

 Long story oversimplified: Mark Zuckerberg made the unilateral decision to kill the website model of the internet. We didn’t even know he had the power to do that. In retrospect, we should have seen it coming. Over the course of the 2010s, Facebook grew to the extent that people sharing our links to their friends on that platform became the primary driver of traffic to the site. Then, in 2014, they abruptly turned off the spigot and killed link-sharing on Facebook.

 If you’re familiar with Cory Doctorow’s essays and books on “enshittification” then you know this general story and I’m not going to paraphrase it too much. For us specifically, it resulted in a few years of floundering and scrabbling and layoffs and damage control and more layoffs. I was a contractor, so I was never officially fired; They published my last piece under my name in 2019 and then at some point shortly afterward they stopped sending me projects. I didn’t know they were really finished with me until they silently revoked my access to the company Slack.

 By horrible coincidence, this was also during Covid. It was rough.

Why am I telling you all of this? If you’re subscribed to me, particularly if you have been for a while, then I thought you might be interested in a little bit of biography, but more to the point, you will hopefully be interested in the news I have that requires all of that biographical context. To quote a cliché, I have good news … and bad news.

 In the years since my departure from Cracked I’ve been trying to salvage my writing career and it’s been real tough because it was, as I’ve often said, the best job I’ve ever fucked up. I fucked it up because I didn’t leverage it. I didn’t start a blog and drop links to it in my articles. I didn’t join Twitter and build up 500,000 followers during an era when that was totally possible for someone doing what I did. I didn’t make many friends within the industry, and those I did make either dropped out of the creative industry altogether or pivoted to stuff like TikTok, so couldn’t help me. Also, two of them died.

 But I now have a relatively respectful thing going on here that I’m still building. It’s small, but it’s growing. And I’ve gone back to writing a book that I had shelved several years ago when my writing career went tits-up. I’ve been posting pieces of that book online as a perk for paid subscribers.

 A few months ago I got an automated email from Substack telling me that another Substack writer had begun recommending my work. I recognized the name of this person (who I feel it would be impolite to name without permission) because they are a relatively well-known novelist. I tracked them down on social media and caught them promoting the segments of my book to their followers. So I got in touch.

 One thing led to another and I wound up being introduced to this writer’s agent, who read my pitch and chapters and then, in a turn of events I’m still stunned about, gave me a contract and asked for a proposal.

 That is the good news. If you’re a paid subscriber and you’ve been waiting for the next chapter and wondering why I stopped posting them, that’s why. I’ve been working on this big document about what this book is about and why it’s important. I’m just finishing it up now.

 But I said there’s bad news, didn’t I? Somebody, at some point, is going to ask who the hell I am.

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