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.
What 2025 Taught Me About Survival and Meaning
This is the 100th edition of "Elephant in the Room", and my most personal. It's the story of survival in face of uncertainty. Edition 100 is about the year that forced me to learn the differenceโand what actually kept me intact when everything felt uncertain.
The Waiting Room We Never Left
"What if a demon were to creep after you one night... and say, 'This life which you live must be lived by you once again and innumerable times more...' Would you throw yourself down and gnash your teeth and curse that demon? Or would you answer, 'Never have I heard anything more divine'?" - Friedrich... Continue Reading →
Wondering If You Should Follow Up After Interviews? Here’s The Answer.
Radio silence after an interview? Should you follow up? Or will it make you look desperate? I wrestled with this myself this year, sending dozens of follow-ups and tracking the results. My finding: while silence usually means rejection, there's a crucial 20% upside you're leaving on the table if you don't act strategically.
Welcome to the World Where Everyone is a Writer and Nobody Reads
Writing that actually moves us requires precisely what AI eliminates: the messy human struggle. George Saunders calls this your "iconic space": the place from which you write stories only you could write. I ask my readers: what will you write that only you can write?
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.
Reports of Content Marketer’s Death Are Greatly Exaggerated
"๐ช๐ฒ'๐ฟ๐ฒ ๐น๐ผ๐ผ๐ธ๐ถ๐ป๐ด ๐ณ๐ผ๐ฟ ๐ฎ ๐๐ผ๐ป๐๐ฒ๐ป๐ ๐ฆ๐๐ฟ๐ฎ๐๐ฒ๐ด๐ถ๐๐ ๐๐ผ ๐ฑ๐ฒ๐ณ๐ถ๐ป๐ฒ ๐ฎ๐ป๐ฑ ๐ฒ๐ ๐ฒ๐ฐ๐๐๐ฒ ๐ผ๐๐ฟ ๐ฐ๐ผ๐ป๐๐ฒ๐ป๐ ๐๐๐ฟ๐ฎ๐๐ฒ๐ด๐..." Sounds like any generic job posting, right? Except this one's for ๐๐ต๐ฎ๐๐๐ฃ๐ง โ the juggernaut that was supposedly eliminating content jobs. Delicious irony, this. The very company poised to make content marketers obsolete... needs content marketers.
Forget AI Imitating Us, We Are Imitating AI
Ever feel like LinkedIn posts sound... a bit too perfect these days? Or like certain words are suddenly everywhere? You're not imagining it. I dive into a fascinating and unsettling trend: we might be starting to sound like AI, not the other way around. Drawing on insights from the Max Planck Institute and literary critics, I explore how platforms and AI tools are subtly reshaping our language, making it more uniform and less uniquely human. It's not just about what we write, but how it impacts trust and authenticity in communication.
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.
When Struggle Was the Signal: AI’s Challenge to Creative Worth
Is the ease of AI fast-tracking the commodification of the human spirit, as Nick Cave eloquently argues? Does a flawlessly AI-written letter of recommendation devalue the genuine effort of a professor, as Ethan Mollick discovered? What happens when the struggle fades, when AI can conjure prose with effortless speed?