Wrote Too Well. AI Suspected.

Jamir Nazir won a Caribbean regional prize at the Commonwealth Short Story Prize. 7,806 entries. One winner from his region. Days later, online commentators ran his story through AI detection tools and declared it machine-written. Granta's own publisher said the judges may have "awarded a prize to an instance of AI plagiarism." Three detection tools were used. Three different verdicts. This is the new plagiarism charge. Easy to throw. Hard to disprove. Burden of proof falls on the writer. I've been working on this problem: collecting AI tells, reverse-engineering prompts, ghostwriting for people who need to prove their own voice on the page. Here's what I've learned about what actually separates human writing from machine writing. Hint: it's not the em dashes.

The Self That Survives the Layoff

A year ago I wrote about an engineer who lost a $150k job and was driving for DoorDash, living in an RV. Last week, out of nowhere, I looked him up. He's now Head of Engineering at a startup. I felt relieved. Not just for him, but for everyone wondering when their number comes up. Wrote about what his story made me think about: identity, layoffs, and the version of yourself that exists outside the job.

When AI becomes Your Therapist

In 2013, Her showed us a man falling in love with his AI operating system. We watched it as science fictionโ€”a little unsettling, but safely distant. That was 13 years ago. Today, people are using AI for therapy. For companionship. For the kind of emotional support we used to get only from other humans.

2025, or What Happened When the Reservoir Ran Dry

When I started this newsletter (back in 2024), I had the confidence of someone who'd never run out of ideas. By this year, the reservoir had run dry. But I kept writing anyway. Here's what I learned from writing 51 newsletters in 2025: โ†’ AI dominated my output (31%) when I planned to write about policy โ†’ Being right about content marketing's comeback didn't prevent months of struggle โ†’ The newsletter became less about expertise, more about documenting uncertainty โ†’ Writing became thinking in public The biggest lesson? Markets can remain irrational longer than you can remain solvent. And that applies to career too.

The AI Revolution’s First Casualties: Why Your Entry-Level Job Disappeared

If you're a recent graduate struggling to land that first role, you're not imagining things. A new paper examining millions of American workers reveals something stark: since ChatGPT went mainstream in late 2022, employment for workers aged 22-25 in AI-exposed occupations has plummeted 13% relative to their older colleagues. The traditional career ladder assumed you started at the bottom and climbed up. AI just removed the bottom rungs entirely.

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