Ranking Headache Types by How Personally Offended I Am by Them
By Ken Hollow, unpaid intern of chaos. Look, I didn’t sign up for headaches. I signed up to manage one (1) fox spirit with delusions…

Another day, another round of “AI is here to kill everything you know and love.” Except, apparently, it’s not. According to The Wall Street Journal, enterprise software — the sprawling beast that runs HR, finance, compliance, and a thousand other cubicle nightmares — isn’t dying anytime soon.
AI may be clever, but it’s not about to rip out the guts of SAP or Oracle and replace them with a chatbot. These systems are too entrenched, too complicated, and too boring for AI to fully absorb. Instead, AI is being bolted onto them like a shiny hood ornament on a very old, very expensive car.
The WSJ put it bluntly: reports of software’s death have been greatly exaggerated. AI isn’t here to kill it. Just haunt it.
The dream of firing your HR software and letting an AI handle PTO requests? Still a dream. Instead, HR software is absorbing AI features like some weird digital amoeba. Now your PTO request comes with “AI-powered insights” about how burned out you are. Thanks, robot.
Meanwhile, compliance tools are adding “predictive AI modules” to flag suspicious activity. Which sounds great until the AI decides that Steve from Accounting is a threat to national security because he expensed too many burritos.
When I told Nana software wasn’t dead, she shrugged and said, “Everything dies eventually. Even code.” Then she tried to convince me to move her entire merch operation onto a “blockchain-powered ritual ledger.” I pretended to lose WiFi.
The big takeaway? Enterprise software is stubbornly alive. AI isn’t its replacement — it’s its awkward new roommate. Investors hyping “the death of software” are selling a fantasy. The reality is a lot duller: boring, entrenched tools getting slowly less painful with AI duct tape slapped on top.
So no, your HR tool isn’t obsolete. Your finance software isn’t vanishing. And your compliance platform will still make you cry once a quarter. AI just makes the crying slightly more automated.
Every time a new technology shows up, someone writes software’s obituary. But enterprise software is like a cockroach in a server room — unkillable, deeply annoying, and always finding new ways to survive. AI may be flashy, but software isn’t going six feet under anytime soon.
So relax. Your tools aren’t dead. They’re just… haunted. And probably invoicing you for another yearly renewal.
Hi. I’m Ken. I run Two Second Solutions, a one-man agency that somehow landed a fox spirit influencer as a client. I drink too much coffee, blog when I need to vent, and regularly update my résumé just in case she sets the office on fire again. I’m not crying — it’s just spell residue.
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