Eight months ago, I made a decision that had nothing to do with my business. Or so I thought. I had spent several years studying AI. Hundreds of hours of reading, testing, and experimenting. And I kept arriving at the same conclusion: the real advantage was not in using AI tools. It was in learning to work with AI as my thinking partner. But a conclusion is not proof, and I was not going to bring this to a single...

Seven sessions into the AI Insider Lab, I was confident I understood what was happening in the room. I had been present for every minute of every call. I use Glasp.co to transcribe each recorded Zoom session and run it through Claude’s analysis, which gives me a detailed read on what was covered, what questions surfaced, and where members are in their thinking. After every session, I review those notes carefully. I thought I had a clear and accurate picture...

The week before I facilitated a structured AI interview exercise live with my AI Insider Lab participant, I ran it on myself first. I do this with everything I teach, but this particular run changed something. AI asked me one question. Then another. It refused to let me summarize early, refused the easy answer, kept pushing until something I had been doing instinctively for decades finally got named back to me, out loud, for the first time. That exercise is...

I am spending this week on the streets of New York, in a street photography workshop with Peter Turnley and a dozen other photographers. On the subway back from Coney Island, a young woman sat down across from me with her eyes closed, listening to music, somewhere far inside her own world. When she opened her eyes for a moment, I waved and told her I would be honored to capture a few photographs of her. She smiled and nodded....

This is issue 700. Every Wednesday since the first week of January 2013, for more than thirteen years, I have shown up in your inbox without missing a week. That is the milestone, and I am proud of it. But the number is not what I want you to take from today. What matters is what stayed fixed while everything around it changed. For 700 weeks, through five different versions of who my company was, the mission never moved. I...

Something happened recently that stopped me mid-sentence and has had me thinking ever since. While demonstrating one of our new apps developed with the help of AI during one of our AI Insider Lab sessions, I shared with our group of senior consultants and advisors that AI has compressed our development time by a factor of 8 to 10x. That number came directly from reflecting on two recent builds, a new app and a member portal, and comparing what they...

Two years ago, these two professionals were indistinguishable. Same caliber of expertise. Same decades of client work. Same reputation in their respective markets. Both heard the same message about AI changing everything. Both believed it intellectually. Both had access to the same tools. Today, one of them operates with a confidence and clarity that clients notice immediately. The other is working harder than ever and falling behind in ways that are difficult to name but impossible to ignore. The difference...

There is a pattern I keep seeing, and it is too consistent to ignore. A senior professional reads an article about AI transforming their industry. They nod. They agree. They may even forward it to a colleague with a note that says, “we should talk about this.” And then they go back to working exactly the way they worked last month. And the month before that. And the month before that. This is not a discipline problem. It is not...

Everyone is asking the wrong question about AI and jobs. The fear is that AI will replace senior professionals. It will not. Not yet, and probably not in the way most people imagine. The real disruption is quieter, more structural, and far more dangerous: AI is eliminating the entry level and junior roles that train the next generation of senior professionals. The pipeline that creates your future replacement, your future partner, your future successor, is breaking. And almost nobody is...

There is an uncomfortable truth hiding inside the AI productivity revolution, and almost nobody is talking about it. The same tool that is supposed to make you sharper may be quietly making you weaker. Not because AI is flawed. Because of how you are using it. Think about what happened with calculators. Once they became standard, we stopped doing mental math. Not gradually. Almost immediately. The skill did not fade because it became irrelevant. It faded because something else handled...