I asked AI to tell me who I am based on how I talk to AI. The fact that this makes perfect sense might be either civilization’s greatest achievement or its quiet ending.
But really, you want to know someone? Don’t read their LinkedIn.
I used to think about my life as a series of data points. But when you get everything you’re supposed to want, you discover that new view is lonelier than you expected. The goals you hit don’t always fill the spaces you emptied to reach them.
I’ve spent years compressing myself into pitches, bios, tweets, executive summaries. Always trying to fit into smaller boxes, tighter definitions. Now I ask AI to expand me back. Pretty fucked up, right?
I spent a decade optimizing for outcomes and control. Built things, sold things, measured everything. It worked. But what was it costing me to be me?
So I shifted. Started chasing a different type of meaning instead of metrics. Started asking different questions. Not “What did you ship?” but “What did you let go?” Not “What’s your growth rate?” but “What’s your learning rate?”
You can exit an executive role but its hard to lose the temperament. I still keep a mental backlog:
Close the gap between what I admire and what I practice
Stop the internal snark
Notice what triggers me
Accept that some things can’t be optimized
Stop whatever you’re doing for a moment and ask yourself: Am I afraid of death because I won’t be able to do this anymore? — X. 29
Why I Talk to Machines
Humans are complicated. Machines are honest about their limits.
When you talk to AI, you have to be explicit or you get something close enough to be painful (I’ve learned this the hard way). This precision is a discipline. You can’t hide behind charm. Just raw specification of what you want and a dose of the right context.
Is it dehumanizing? Sometimes. But it’s also quite humanizing because you have to decide exactly what you mean. I’m testing whether I can bear my best intentions without the soundtrack of my rationalizations.
Today I am a Founder who looked at my own data trail and decided to keep looking.
I’m not healed but I am someone trying to be more honest about what things actually cost.
I believe in grieving the future while building it. Because every shiny thing casts a shadow. Build without acknowledging what you’re losing, and the first challenge knocks it over.
A few things I’ve learned:
The opposite of scale is intimacy.
I built a ladder to the ceiling and learned the room was the problem.
Obsolescence isn’t decay. It’s proof something lived.
Clarity is love that doesn’t need to win.
Not an Ending
I start another conversation. Same questions, different words. Each chat a new attempt to understand myself through the mirror of something that doesn’t judge.
The way I am? An ongoing negotiation between who I was trained to be and who I’m choosing to become. Messy. Real enough to share without lying.