The Turning Point
I stood in my garage with my phone to my ear, and I knew that whatever I said next was going to change everything.
The recruiter on the other end had been patient for months. A company in San Francisco had been courting me for a senior technical role, the kind of work I’d spent years getting good at. Architecting scaled systems. Mentoring engineers. Staying close to the code. It was a comfortable next step.
At the same time, my CEO had been pushing me toward something else entirely: an executive role, heading my division, with a plan for it to become its own company. The catch was explicit. If I took the executive role, it was purely leadership: no coding, no architecture, nothing I loved about the work. If I stayed on the technical path, it was purely tactical, reporting to a new hire who would make decisions I’d have to support whether I agreed with them or not.
The recruiter needed an answer by end of day. My CEO needed one too. Three decisions, converging at once, no middle ground for me to retreat to. The only way forward was through.
That’s the day I learned what an anxiety attack feels like.
Here’s what I know now that I didn’t know then: the anxiety was honest.
What felt like a career decision was actually a career change. Not a promotion. Not a step up the ladder. A change of career. The skills that got me to that moment in the garage, the ones that made me someone worth recruiting, worth promoting, would not be the skills that made me successful in the role I was about to take. I was choosing to leave one profession and enter another, with almost no experience in the new one.
Most people don’t get a moment like that. The transition happens gradually, a new title here, a few new responsibilities there, until one day you realize you’re a leader who never decided to become one. That gradual path is comfortable. It’s also the reason so many people never actually make the crossing.
Think about what it looks like when someone starts making chairs.
You get good at it. Other people notice. They want more chairs than you can make alone, so you teach other people your approach. Now you’re a chair team lead. You’re still in the middle of the making, still doing the thing you love. The transition feels natural.
But demand grows. You bring in more people. Your best chair makers start training the new ones, and now you’re watching other people make chairs instead of making them yourself. “Chair Manager” feels different. Uncomfortable in a way that’s hard to name.
Keep going and you end up responsible for the success or failure of the whole operation. More layers exist between you and making a chair. If you want more and better chairs, you have to stop making them. You spend your days on the things that allow other people to make chairs: the people, the environment, the organization. You went from one career to another, and most people don’t notice when it happened.
Those who fail the transition are the ones who treat the new role as a more senior version of the old one. They stay close to the technical work. They make decisions their teams should be making. They treat the people below them as extensions of their own hands instead of as a team they’re responsible for building. It’s toxic to the people who report to them, and it’s a dead end for the leader who can’t let go.
They never let go of the chair.
No one tells you that there’s a valley between the two careers.
You spent years developing real skill. You know what competence feels like. You know what it feels like to be good at something, to have instincts you can trust, to walk into a problem and know what to do. Then you step into leadership and you’re a beginner again. The things that made you credible in your last role don’t transfer. Some of the instincts you built over years are the wrong instincts for this work. You don’t know what you don’t know, and you can feel it.
Most people with leadership titles never crossed the valley. The transition happened gradually enough that there was no moment of reckoning, no point where the gap between the old career and the new one became impossible to ignore. They walked into leadership carrying the same habits, the same instincts, the same definition of what good work looks like. The valley was always there. Most never went looking for it. When it inevitably showed up anyway, they called it something else so they could comfortably ignore it.
Others recognize the valley for what it is. They decide whatever the crossing would cost isn’t worth it. And they turn back anyway. They stop at the edge, keep one foot in the old career, fill their days with work their teams are qualified and eager to do, leaving the work their teams are depending on them to do undone.
The anxiety attack in my garage was the right response. I felt it acutely. I just didn’t have words for it yet. I do now.
The people who cross the valley are the ones who treat leadership as a new discipline requiring the same intentional investment they gave to their previous career. The same reps, the same practice, the same willingness to be bad at something before you get good at it. They don’t assume the title comes with the skills. They go learn the skills to become worthy of the title.
Imposter syndrome is appropriate. This should feel like starting a new career. Because it is.
If you decide to cross the valley, you owe it to the people who would follow you to go all in. That means accepting that you’re a beginner, doing the work to stop being one, and never pretending otherwise. Half-assed leaders make half-assed teams. The people who follow you deserve better than someone who wandered into leadership because it was the next rung on a ladder.
I took a difficult path across the valley, and I’m still building on the other side.
What I found there wasn’t order. The chaos doesn’t relent when you cross. What changes is how you flow. You stop treating it as the problem to overcome and start building inside it instead. Small islands of coherence in the middle of the churn, where the right people find each other, where the work feels like it matters, where something real gets made. Not because anyone ordered it into existence. Because you built the conditions for it, and the islands became inevitable.
That’s what this publication is. Field notes from inside the work. What islands look like when they’re forming, what stops most people from building them, and what this work relentlessly demands. Not a framework. Not a polished set of principles for a wall. Notes from someone who crossed the valley and kept building.
Chaos is the medium. Coherence is the achievement. Everything here is about how that happens in practice.