Identity & Transformation
July 3, 2026
Transforming the Identity License
Every technology transformation plan accounts for data, systems, and timelines. Almost none of them account for the people who have to let go of who they were t...
Short essays on enterprise AI, forward deployed product work, customer reality, systems thinking, and the conditions that make execution either easier or unnecessarily painful.
Every technology transformation plan accounts for data, systems, and timelines. Almost none of them account for the people who have to let go of who they were t...
The bottleneck in most rooms full of experts isn't expertise. It's translation. And AI is making that more true, not less.
Santiago kept walking not because he knew where he was going, but because stopping would have meant never knowing. That's the only strategy that works.
The biggest mistake people make with AI isn't misunderstanding the technology. It's misunderstanding their role in relation to it.
Who are you without the job? It's a question most of us avoid until we can't anymore. AI is making it harder to avoid.
We expect others to respond to information they don't have. Turns out, so does AI. The problem is older than both of us.
The Luddites weren't wrong. They were just living through the part of the story where the ending wasn't visible yet. So are we.
The most interesting question about AI isn't what it can do. It's what it gives us back.
The blockers are never where you expect them. I've known this for years. I just didn't expect my first week at a new job to prove it quite so efficiently.
The biggest blockers to enterprise AI adoption usually aren’t model quality or infrastructure. They’re alignment, trust, workflow design, and organizational ambiguity.