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- My AI Bar Fight
I walked into Le Diplomate a little early.
I was meeting Blaire, my colleague, after work. I slid onto a barstool, ordered nothing yet, and opened my laptop for one more Zoom call. Taxes. Important, but not interesting.
What was interesting was the man to my left.
I overheard phrases drift through the bar noise: real estate, content modules, platform. The kind of language you only half-notice until your pattern recognition kicks in.
After my call, I leaned over.
“What are you working on?”
“A marketing platform for high-end real estate professionals.”
Neat, I thought.
Then the real conversation started.
To my right sat a woman I had never met before, with the unmistakable posture of someone sharp. Seasoned. Educated. Confident. She was eating French onion soup like she knew it was good and did not need validation.
“So,” she asked, “are you in tech?”
“I suppose you could say that.”
She told me what she did: branding, marketing, messaging, identity work at the intersection of policy and public affairs. Serious work. Human work.
Somehow, inevitably, we landed on AI.
And that is when her tone shifted.
She talked about fear.
About jobs disappearing.
About artistry being hollowed out.
About friends at her company already feeling the ground move under their feet.
So I asked her the question I cannot stop asking lately.
Isn’t the new skill taste?
Isn’t it understanding something so deeply that you can get to the right outcome faster because the machine executes what you already know how to see?
She bristled.
“I think AI is incredibly deceptive,” she said. “I take a lot of pride in my work.”
Fair.
So I pushed a little.
“If you are truly great at what you do, and you know how to use your tools, wouldn’t that make your company more money? Wouldn’t efficiency plus judgment actually increase your value?”
She paused.
“Well… what if that takes people’s jobs?”
And there it was.
The real fear is not AI.
It is replacement.
I told her something that probably did not make me popular.
“Survival-of-the-fittest environments are not inherently bad. Learn to use the tools better than the people next to you. That is how you stay relevant. That is how you win.”
She stared into her soup.
Then she said she was waiting for doomsday. That when AI finally takes over, she would "move to an estate in Massachusetts and read and write all day.
I could not help myself.
“That is going to take a lot of money,” I said.
“So you either need to make the tools work for you… or marry someone very wealthy.”
At that moment, Blaire arrived, right on cue.
As the conversation wound down, the woman smiled and said,
“This has been a very stimulating conversation.”
She was not wrong.
What stuck with me afterward
Later, talking it through with Blaire, as she and her daughter ordered dinner, three things crystallized.
(But first, . . . c’mon)
Blaire her daughter a couple weeks ago.
1. I have never been more excited about AI.
I have always been good at getting ideas to 70 percent. AI gives me superpowers to take them to 100 percent. Not instead of me, but because of me.
2. AI adoption is wildly regional.
Living in San Francisco skews your reality. Here, AI seeps in through osmosis. In D.C., and many other places, the tooling in some areas may not be embraced at all. Same tools. Completely different mindset.
3. The resistance is not about age.
I expected a younger, smart, highly educated professional to be all in. She was not. Charlene Li said it well in her piece yesterday. Resistance to AI has nothing to do with generation. It has everything to do with identity, power, and fear of displacement.
I also keep coming back to Dan Martell’s framing.
AI is the new electricity.
But it is also not.
Electricity changed how we lived.
It did not learn you.
It did not compound.
It did not get better every time you used it.
AI does.
Which means this moment is not about tools.
It is about orientation.
Are you waiting for doomsday?
Or are you learning how to conduct the current?
Because the future is not replacing people with machines.
It is replacing people who refuse to evolve with people who have taste, judgment, and the courage to learn in public.
And that conversation, over a bar at Le Diplomate, made that clearer than any headline ever could.
Community Notes:
1) Holiday Shopping? Support Anya Emerson and Jonah Staw
Mightly, Inc is a women-founded and women-led team of brands - Mightly, Of an Origin and Italeau, committed to thoughtful design, ethical production and everyday essentials. Across kids’ apparel, women’s clothing, bedding and footwear, we build our products the right way—from GOTS-certified organic cotton and Fair Trade factories to small-batch, artisan craftsmanship—so customers never have to choose between style, comfort, and values. Our community cares because every purchase supports a more just, transparent, and sustainable supply chain, proving that better business models can win.
2) Order Jonathan’s Bloom’s book, Blindspots, great for founders and CEO’s to see around corners they otherwise wouldn’t!
🇬🇧 UK: https://amazon.co.uk/dp/B0G53X5ZS7
🇺🇸 US: https://amazon.com/dp/B0G53X5ZS7