Most people ask AI for information. But what happens when you start giving it information — about you — so that it starts to understand you back? That’s the question behind this episode, built out of about six months of my own quiet experiment, plus what happened when I finally put it into words at a conference last week.
The Dan Pink Experiment
This whole idea traces back to Dan Pink, who gave AI a set of pointed questions — what are my blind spots, what lies do I tell myself, where do you see me in five years — and told it to act like a brutally honest trusted advisor. I’d been doing versions of this for months without realizing I was running the same experiment.
Why AI Gets More Useful the Longer You Use It
Unlike a search engine that resets every time, AI accumulates context — every show I’ve recorded, my childhood, retirement plans, even a plumbing problem in my basement. That accumulated history is what turns a tool into something closer to a conversation partner.
What Months of “Friday Night Conversations” Added Up To
I didn’t realize how many separate conversations — about work, about weight loss, about my podcasting habits — were quietly circling the same handful of themes until AI assembled them into one picture. The insight wasn’t new information. It was old information finally put together.
Continuity, Not Intelligence
The real value here isn’t AI being smart — it’s AI remembering. It’s the ability to aggregate months of scattered conversations into one coherent thread, which is a genuinely different kind of usefulness than answering trivia.
The Big Caution: What AI Can’t Actually Know
I’m honest in this episode about the limits, especially around any question that asks AI what other people think of you behind your back. It has no access to that — whatever it gives you is invented, delivered with the same confident tone as everything else.
The “Dear Me” Letter
One of my favorite exercises from this whole process: asking AI to write you a kind letter, as if it were you, pointing out what you’re missing about yourself. Mine had some real blind spots in it I wasn’t expecting.
The goal was never to let AI define me — it’s to let it be a thoughtful conversation partner that helps me examine my own thinking over time. If you try this, I’d genuinely love to hear what came back for you.
You can find everything I do at jillfromthenorthwoods.com. My email is [email protected].
Dan Pink's Video https://www.youtube.com/watch?v=PjTaZvvOtxU
Jill’s Links
http://jillfromthenorthwoods.com
https://www.youtube.com/@startwithsmallsteps
https://www.buymeacoffee.com/startwithsmallsteps
https://twitter.com/schmern
Email the podcast at [email protected]
By choosing to watch this video or listen to this podcast, you acknowledge that you are doing so of your own free will. The content shared here reflects personal experiences and opinions and is intended for informational and educational purposes only. I am not a software developer, data scientist, or AI professional. Any tips, tools, or suggestions offered should not be considered a substitute for professional technical advice. AI tools and platforms change frequently — always verify current features, pricing, and terms directly with the providers. You are solely responsible for any decisions or actions you take based on this content.
