Teaching GPT-5 to Sound More Like Me
By Ken Hollow, AI wrangler, burnout survivor, and reluctant personal brand When GPT-5 dropped, I thought, “Perfect. Finally, an assistant who can handle my tone…

By Ken Hollow, unwilling author of receipt novels
Expense reports are the worst kind of creative writing: bureaucratic fanfiction. You take mundane events — a taxi ride, a coffee, a hotel room — and rewrite them into tortured corporate prose that might, if the gods of accounting smile upon you, result in partial reimbursement six months later. Meanwhile, executives are out here expensing helicopters like it’s UberX.
The process goes like this:
And then: rejection. Because you put “lunch” instead of “meal.”
Employees get flagged for:
Executives sail through with:
It’s not about rules. It’s about hierarchy. Expense reports are just another way to remind you where you sit.
Expense report rejection emails always sound like they were written by a disappointed parent:
Nana, of course, submits expense reports that read like grimoires:
Accounting once flagged her for “unclear purpose.” She marched into their office with a raccoon and said, “Justification.” Approved instantly.
It’s not finance. It’s fanfiction. And we’re all forced to write it.
Expense reports aren’t about accountability. They’re about bureaucracy feeding on your time. They’re novels of nonsense, receipts as plot devices, rejection emails as cliffhangers.
Meanwhile, executives are out here writing blank checks to themselves. But sure — let’s interrogate my $6 latte like it’s Watergate.
Ken Hollow, unpaid novelist of receipts, rejected author of sandwich epics
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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