August 8, 2026
Everyone You Think is Ahead is Just Lost Out Loud

A colleague messaged me this week because she couldn't get into a couple of our internal AI tools. We hopped on a call, she shared her screen, we backed out to the login page and tried again...and it just worked. This is my whole value as a colleague: I show up and the software gets nervous. The other tool, the one she actually needed, was still broken.
Being the product person I am, I got nosy. I asked her what was she trying to do in the first place.
Turns out she'd built herself a whole workaround. She'd been loading a scope of work and a stack of our documentation into a self-hosted chat tool we run, and asking it questions from there. Not because it was better. Because she didn't want company material going into Gemini. Security, data, all the stuff you're supposed to worry about.
Except our Google Workspace is the enterprise version. We have contracts. That material isn't going anywhere and isn't training anything. She could have been asking Gemini all along. She'd been taking the long way around for weeks to protect something that was already protected.
Nothing she did was wrong. She was cautious because cautious is the right thing to be. She built her own knowledge base without anyone telling her to. She'd thought harder about where company data goes than most people ever do. She uses AI every single day. And she still felt like she was doing it wrong somehow, because there's always one more tool she hadn't gotten to.
I know the feeling, and I'm supposedly the one up ahead. I build this stuff. And I still feel like I'm behind every week, because the tools change faster than anyone can track them. Not faster than she can track them. Faster than anyone can. Including the people who make them.
I showed her Gems. The custom setups inside Gemini where you dump your files and instructions in one place and it stays pointed at them. Same idea she'd already built the hard way, except now it's one less thing to maintain. She said she was going to have such a good time now.
If you feel behind on AI, I don't think behind exists. The ground is moving under everyone, all the time. The people who look ahead of you aren't holding a better map. They're just slightly more comfortable being lost out loud.
Feel free to be lost and please, for everyone's benefit be lost out loud. We're all learning from each other.
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I write about AI in plain English every other Sunday. No hype, no jargon — just the stuff that actually helps.
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