The Observer's Notebook

  AI Is Making Your Decision Problem Worse You don't have an ideas problem. You never did. AI just made it impossible to ignore that the real problem is something else entirely. There is a quiet crisis running through founder culture right now, and it doesn't look like failure. It doesn't look like confusion. It looks like the opposite of those things. Tabs open. Docs full of strategy. ChatGPT threads stacked six conversations deep. A to-do list that keeps getting longer in the places it's supposed to be getting shorter. From the outside, it looks like a person who has their hands on things. From the inside, it feels like running in place. That's not productivity. That's hesitation with better branding. What AI is Actually Giving You AI is extraordinarily good at one thing: generating options. Ask it a question, any question, and you will not get an answer. You will get a spectrum. Ten strategies. Seven frameworks. Five positioning angles. Multiple "it depe...

  Your Business Isn’t Making Money. Here’s What I’d Actually Fix. I need to say this clean, because if I soften it, you’ll stay stuck longer than you need to. When someone comes to me and says, “My business isn’t making money, what should I fix,” they’re almost always asking the wrong question. Not because they’re incapable. Not because they’re lazy. But because they’ve already spent months, sometimes years, trying to fix the wrong layer. They’ve adjusted their content. They’ve redesigned their website. They’ve tried new platforms, new hooks, new offers, new pricing. And still, nothing compounds. So they assume something is broken. It’s usually not broken. It’s misoriented. And that’s a very different problem. What Actually Happens Inside a Direction Session Let me give you a real look at what happens when someone sits across from me, whether that’s a paid Direction Session or one of the rare ones I gift. They don’t come in saying, “My offer is unclear.” They say things like: “I’m ...