The Observer's Notebook

  You're Not Stuck Because You're Not Trying. You're Stuck Because You're Solving the Wrong Problem. There's a specific kind of frustration that doesn't get talked about enough in the founder space. It's not the frustration of not doing enough. It's the frustration of doing a lot of real, legitimate work, the kind that should be moving things, and still feeling like you're standing in roughly the same place you were six months ago. If that's where you are right now, the first thing I want to say is that it's probably not what you think it is. It's not a focus problem. It's not a discipline problem. It's not that you need better systems, a clearer morning routine, or a coach to hold you accountable. It's that the problem you've been solving isn't the problem that's actually stalling you. Why Smart Founders Are Specifically Vulnerable to This The founders I work with are not passive. They're not waiting for thing...

  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...

  The Work Behind My Work Why I Do What I Do There’s usually a moment before someone finds me. Nothing has collapsed. From the outside, things even look successful. The business exists. The experience is there. Revenue has happened before. And yet something feels heavier than it should. Decisions take longer. Marketing requires more effort than it used to. Momentum exists, but clarity doesn’t. Most of the founders I work with arrive here quietly. Not because they failed. Because they evolved faster than the strategy they built their success on. I understand that moment intimately, because I’ve lived it more than once. I Didn’t Start in Strategy. I Started in Survival. I became a mother young. Before stability. Before certainty. Before having the luxury of figuring life out slowly. I learned early how to build while carrying responsibility. While finishing school. While working. While navigating environments that required resilience long before I understood the word. Later, I built ...