Judgment Was Supposed to Be the Moat. The Bitter Lesson Says Otherwise.

Most of us believe org chaos protects our jobs. The reasoning goes: processes are messy, decisions are undocumented, judgment lives in people's heads โ€” so AI can't touch what it can't even see clearly. I used to believe this too. Until I ran a small experiment that made me question it. Turns out, AI didn't need my process. It just needed to see my output.

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.

What I Learned from Scott Adams: Systems, Stacks, and Selfishness

I started my very first newsletter quoting Scott Adamโ€™s, Systems > Goals Thatโ€™s how deeply I internalized this particular insight. With the news of his passing yesterday, I pondered over his final message: "I had an amazing life... If you got any benefits from my work, I'm asking that you pay it forward... Be useful." Thatโ€™s one beautiful parting message. And one of the 3 top lessons that most resonated with me.

Why CORE Traits Matter More Than Skills in the AI era

We posit it's because of CORE traits: 4 unchanging human qualities that will outlast every technical skill you'll ever learn. It's not nepotism, favoritism, or flattery. It's CORE traits that don't show up on resumes. And in the AI era, these traits matter more than ever

The Writing Looks ChatGPTish

When people say they can spot AI writing from a mile, what do they actually mean? Excessive em dashes? Short paragraphs? Words like "delve" and "meticulous"? LinkedIn was full of cringe long before ChatGPT. AI didn't invent buzzwords or performative prose. The algorithm simply picked what went viral. We're pretending that before ChatGPT, all writing flowed from pure creativity. As if "On Writing Well" and "The Elements of Style" never existed. We always followed rules. But our inability to follow them perfectly made our writing unique. AI follows rules perfectly. That's the problem. I explore this paradox in this essay.

Disintermediated? Think Again. The Rise of the Digital Gatekeeper

Ever wonder why those unskippable ads on your streaming service are getting worse? Or how a market sprang up in a WWII POW camp? It all comes back to the middleman. I dive into why brokers are essential for markets to thrive, and how they've evolved from mere facilitators to powerful gatekeepers. Discover the surprising truth behind why markets need brokers, and when they become a problem you can't ignore.

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