Hello friend,
Why you're getting this: This is my Friends Newsletter; my semi-structured brain dump on business, tech, therapy, and whatever else I’d normally corner you about over dinner. Unsubscribe anytime (I won’t cry, but my AI assistant might).
Here’s what I’m thinking about…
We spent the last 30 years telling kids to learn to code.
Now we have AI that can build an app from a napkin sketch. In 14 seconds.
We glorified spreadsheets and strategy decks.
Now GPT-5 can rip through an MBA case study while you’re still reading the prompt.
We told everyone to become “knowledge workers.”
Oops.
I used to think AI would come for truck drivers first.
Turns out?
It came for marketing managers.
It came for product analysts.
It came for your cousin who formats pitch decks for a living.
Knowledge work is the new factory line.
And ChatGPT is the robot.
Here’s the plot twist nobody saw coming:
AI can do the work. But it can’t make you care.
What’s becoming scarce; and therefore valuable; isn’t knowledge.
It’s:
AI can write 100 tweets in 5 seconds.
But it can’t be funny on purpose.
Or emotionally attuned.
Or make a room feel warm when it walks in.
We’re moving into an era where the most important skill is being interesting.
Relatable.
Curious.
Magnetic.
If AI is your intern, your real job becomes:
And if you can do that?
You’re going to eat.
Here’s my short list of unautomatable careers:
AI can generate infinite noise.
The humans who shape signal? They’ll win.
In a world of infinite content, people want real humans to hold onto.
Think about it:
The AI revolution isn’t about replacing humans.
It’s about removing all the stuff that made humans feel replaceable.
Here’s your new syllabus:
This doesn’t mean becoming a TikTok clown.
It means being:
The rarest skill in the AI age is being unmistakably you.
Still running my empire of bootstrapped misfits and weird internet businesses.
Still trying to reduce my screen time and failing daily.
Still hiring an AI operator if you’re an automation wizard with taste.
Still reading submissions from human writers (if you can move me, email me).
1. Are we all doomed?
No. But mid-level strategy consultants might be.
2. What’s the most future-proof skill?
Taste. Always has been.
3. Will AI replace my job?
Probably the worst parts. You’ll either adapt—or be replaced by someone who did.
4. Can AI ever be funny?
Not on purpose. It doesn’t have trauma yet.
5. Should I become a creator?
No. But you should learn to share what you know in your own voice.
6. Isn’t this just another hype cycle?
Yes. But some hype cycles change everything.
7. Should my kid learn to code?
Sure. But also teach them storytelling, psychology, and how to host a good dinner.
8. Is charisma the new resume?
Yes. Sorry.
9. What about technical skills?
Still valuable. Just less differentiated.
10. So I should lean into being more… human?
Yes. As loudly and weirdly as possible.
That’s all for now…
The future belongs to the most human humans.
Get Your Copy of Never Enough at https://www.neverenough.com
Did you enjoy this newsletter? Say thanks by checking out one of my businesses:
