When Kayla and I set out to build our first Pain Retreat, we knew we’d be doing something meaningful.
What we didn’t know was that the first layer of pain would be in the negotiation itself.
We weren’t arguing.
We were co-creating.
But also… debating cost structures like we were prepping for a UN vote.
And then came our third team member: ChatGPT.
ChatGPT: The Calm One in the Group Chat
At some point, we both stopped replying directly to each other and started copy-pasting each other’s messages into ChatGPT.
Kayla:
“The Queen Suite went from 30k to 36k, Terrace 20k to 29k, Dorm 7.5k to 22k… and now you’re suggesting to subtract this as it’s a ‘true cost’??”
Me to GPT:
“How do I explain this without sounding defensive?”
Then came:
“My main takeaway from all of this is that you are inflating Aavya’s value.”
At that point, I asked ChatGPT:
“Please respond to this with calm, facts, and a little emotional intelligence — but don’t make it sound like I’m surrendering.”
Kayla, meanwhile, wasn’t holding back. She sent:
“My BFF GPT says this is still undervaluing the curriculum.”
“You’re quoting me even more than you did the first time.”
“I also agree with my BFF when I say there’s some absence of transparency.”
We had officially reached a point where our AI was the middleman, writing both sides of the argument better than either of us could.
Honestly, It Worked
Without ChatGPT, this could’ve taken a week, three awkward voice notes, and possibly a shared Excel doc that never got opened again.
Instead?
- We built the deal in two days
- We saw the same numbers, interpreted through slightly different emotional filters
- We aligned — faster than most people decide between masala chai or oat milk cappuccino in Tapovan
And the best part? We stayed funny and friends through all of it.
Final Take
We agreed on a model.
It’s clean, functional, and lets both sides win.
But more than anything — it got built with honesty, stubbornness, mutual respect, and a very calm robot.
This isn’t a pitch for the Pain Retreat (though yes, it’s happening).
It’s just a short ode to what happens when you care too much, want to be fair, and let AI handle the worst of the emotional typing.
Pain reduced.
Drama avoided.
GPT, you did good.
