The Observer's Notebook

  Why My Content Isn't Converting There is a specific kind of frustration that does not get talked about enough in business spaces. It is not the frustration of being ignored. It is not the frustration of putting something out and hearing nothing back. It is the frustration of being told, repeatedly, that your content is amazing -- and still having nothing to show for it commercially. You know this one. The post that got saved four hundred times and generated zero inquiries. The caption someone screenshotted and sent to three friends and not one of those friends became a client. The email that got a 60% open rate and a flood of "I felt so seen by this" replies and then a conversion rate of absolutely nothing. The engagement is there. The warmth is there. The comments are kind and the DMs are enthusiastic and people keep telling you that you should write a book. And then you look at your revenue and the numbers do not match the reception. This is not a visibility problem. ...

  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 ...