My job hunt, brought to you by Artificial Intelligence™

The tool that writes my rejection letters also wants me to evangelize it

The tool that’s making me unemployable is also the tool every employer demands I master. Ho boy, that’s 2025 in a nutshell.

I have one tab open with a job description that practically begs for “AI proficiency,” and another tab where I'm watching that same AI cheerfully automate everything I used to get paid for. A third tab features a news article claiming the end of civilization is near, due to the impact of the first two tabs.

Meanwhile, I'm hovering over the “Submit” button on a friend’s FAANG referral like it's going to electrocute me. Click, and I get another rejection—this one written by a bot, which somehow feels like rejection from both the company and the friend who referred me. Don’t click, and it looks like I didn’t take their effort seriously. Either way, I lose.

It has now been 590 days since I last had a job.

At this point, the number doesn’t matter anymore—it could be 400, 1,000, the letter X, or a hieroglyph that nobody has translated yet. The number buzzes in the background like a mosquito that won’t die.

But it's not really about the days anyway. It's about the math of being too senior for the jobs that want “junior rockstars” and too junior for the ones that are looking for “senior thought leaders.” Referrals trickle in from kind friends who still have faith, which feels less like opportunity and more like IOUs I’ll never repay. Every interview feels like a slot machine I’m not qualified to play, but I keep feeding it quarters anyway.

“Why don't you just freelance again?” friends ask, like I can magically time-travel back to 2012 Miami when WordPress gigs paid rent and clients still thought you needed an actual human to build websites. Back then, freelancing was feast or famine, sure, but at least there was an occasional feast.

Now? The famine's automated. Those middle-class web jobs have been devoured by Wix templates, $15-a-month SaaS subscriptions, and AI tools that can spit out a landing page faster than I can order a Publix Sub.

And THAT is the core irony, isn’t it? AI is simultaneously my executioner AND my résumé's best friend. Every job posting says some version of "seeking candidates who leverage AI tools." (Translation: “We need someone to operate the machine that made their job obsolete.”) I’m supposed to evangelize AI like it's my personal savior while knowing damn well it's the reason I’m refreshing my inbox like a lab rat with a broken dopamine lever.

It’s not just me, either. Recent grads are out here competing with their own homework assignments rewritten by ChatGPT. Mid-career folks are frantically rebranding as “AI consultants” overnight, which feels about as convincing as slapping a “UNDER NEW MANAGEMENT” sign on the Titanic. Meanwhile, every company, large AND small, is playing the same game of corporate theater: “Look at us, innovating with AI!” while quietly firing half their staff because they figured out how to automate half of the work.

And here I am, expected to convince someone—anyone—that I can help them navigate the same tool that shoved me into this corner.

Which, to be fair, I can. I’ve put in the hours, built workflows, wrappers, and even an Obsidian plugin. I wrangled the bugs, discovered where AI works brilliantly and where it face-plants spectacularly.

Hell, I even stared into the nightmare fuel of a neural network.

But that’s the problem, though—you don’t get hired for surviving the paradox. You get hired for selling the magic trick, even when you know where the trapdoor is.

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I tested this paradox yesterday. Asked Claude Code to “add accessibility tests” to a project, stepped away for, I don’t know, thirty seconds to grab water, came back to find it had birthed 1,500 lines of fever-dream code. Then, in what I can only describe as heroic self-awareness, it generated another 3,000 lines to fix the bugs it had just created. Layer upon layer, like a toddler stacking blocks higher and higher until the tower inevitably wobbles and crashes. I just stared at the screen, wondering if the AI had invented a new form of performance art.

The essay written to justify itself inside CLAUDE.md was very well composed, for what it’s worth.

That’s the paradox in miniature: AI will cheerfully solve a problem by creating three new ones. The same way it’s supposed to “solve” the job market—by making everyone more efficient—while leaving thousands of us standing around holding résumés like expired lottery tickets.

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So no, I’m not quitting AI. That would be career suicide at this point. But as much as I still find the technology fascinating, I’m not exactly trusting it either. Most days, it feels like I’m driving a car that keeps swapping the brake and accelerator to see what I’ll do. So I keep tinkering, keep applying, keep testing the edges of what this thing can do.

Waiting, I guess, for the day when the tool that took my job decides to give it back.