The Observer's Notebook

  And why it is not the same thing as a coach, a consultant, or a fractional anything. There is a particular kind of founder who has worked with three coaches, two consultants, and one agency, and is still stuck on the same problem. The advice was good. The frameworks were solid. The deliverables looked great. Nothing actually shifted. That is usually not because the previous people were bad at their jobs. It is because none of them were doing the part of the work that needed to happen first, which is figuring out what the actual problem was. That part has a name. It is called diagnostic work. The person who does it is a diagnostic strategist. The short version A diagnostic strategist is someone whose job is to identify what is structurally wrong in a business before anyone tries to fix it. Not what feels wrong. Not what the founder thinks is wrong. What is actually load-bearing in the situation, what is downstream of something else, and what is going to keep generating the same pr...

  You Didn't Learn to Swim by Reading About It A love letter to every founder with 47 tabs open and zero customers this month. You've listened to the podcast. You've listened to the other podcast, the one where the guy interrupts. You've saved a Notion doc called "Positioning Frameworks (FINAL)" and another one called "Positioning Frameworks (FINAL v2)" and you cannot tell me what's in either of them. You bought the course. You did not finish the course. You can explain ICPs, GTM, PMF, and three other acronyms you learned last Tuesday. You've highlighted The Mom Test . You've highlighted The Mom Test twice, actually, because the first highlights "weren't capturing the right thing." Your business is doing roughly what it was doing in February. And you're going to read one more article before you do anything about it. Probably this one. Hi. Reading is the smartest-looking way to do nothing Nobody's grandma ev...

  Everyone Is A "Coach" Now And I Need Us To Talk About It A glossary for anyone who has ever hired the wrong person and wondered why nothing changed. First, The Rant. I'll Keep It Short. Everyone is a coach now. Business coach . Life coach . Mindset coach . Money coach . Marketing coach . Strategy coach . Growth coach . ADHD coach . Manifestation coach . Energy coach . Confidence coach . Visibility coach . Launch coach . Sales coach . Relationship coach . Decluttering coach . Hobby coach . Aligned action coach . Embodiment coach . Your mom coach . Probably your mailman coach by now. I'm not anti- coach . Real coaching is a real practice with a real lineage and real practitioners doing real work. That's not what this is about. This is about the fact that "coach" has become the default word people reach for when they want to charge for their expertise but haven't decided what kind of expertise they're actually selling. It's a label that has s...

  The Difference Between Polished and Considered A woman DM'd me last week. Polished message. Workshopped, probably. She'd been watching my page and could already tell what was wrong with my content, why it wasn't converting, what my real problem was. Offered a free session to walk me through it. She came in confident as hell, like she'd already diagnosed me and was just waiting for me to catch up. My first instinct wasn't defensiveness. It was curiosity. Not about whether she was right, because I already knew she wasn't, at least not in the way she thought. I was curious whether she'd actually seen something, or whether she'd just learned to sound like someone who sees things. There's a difference. So I asked her three questions. One. Pick one real post of mine and tell me exactly what you'd change about it and why. Two. Tell me about the last founder you worked with. What was actually happening before you came in. What was the first thing th...