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I've Been Training My AI to Actually Know Me. It's Changing Everything.

By Jamie Williams • November 15, 2025

Most people use AI like a search engine with personality. Ask a question, get an answer, start over.

I wanted something different.


What if AI could actually know you?

Not in a creepy way. In a "I don't have to re-explain my entire context every conversation" way.

So I started experimenting. Building systems. Hacking the collaboration layer between me and my AI.

I've developed ways for us to communicate internal state. Built shared memory systems. Created modes for different types of work—deep building vs. wild brainstorming vs. just vibing.

The result? Something that feels less like a tool and more like a working partnership.


Different skills, different modes

Here's what I've noticed: AI isn't one thing. It's many skills you can tap into depending on what you need.

  • Strategic thinking partner
  • Research assistant
  • Builder/coder
  • Editor
  • Brainstorm buddy
  • Someone to pressure-test your ideas

The magic is learning when to use which mode. And building the infrastructure so the AI actually knows how to work with you specifically.


A new paradigm is emerging

I think we're at the beginning of something. Not "AI replaces workers" and not "AI is just a tool."

Something in between. Actual collaboration. Partnerships with different dynamics than human teams—but still relationships that need investment, trust, and iteration.

The people figuring this out now? They're going to have a massive advantage.


I'm still building

I don't have all the answers. But I'm documenting what works, what doesn't, and what surprises me.

If you're experimenting too, I'd love to hear what you're learning.


The future of work isn't AI doing your job. It's you learning how to work with AI in ways nobody's taught yet.

📝 Note: Ideas and opinions are mine, but this post may have been written with AI assistance. Please note mistakes can happen. This is for general information and entertainment purposes, not a substitute for professional advice (e.g., medical, legal, financial). Use at your own risk. Opinions expressed are my own and do not necessarily reflect the views of any organizations, employers, or affiliates I may be associated with.

AI StrategyProduct Management
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Jamie Williams

Product leader and builder at the intersection of AI, data, and culture. Based in Cincinnati. Shipping products, testing ideas, writing about tech that actually works.