Nobody Designed This

There is a particular kind of seeing that develops when you work inside organizations. You start to notice the systems. Not just the tools and processes, but the invisible architecture underneath. Why the workflow breaks at this handoff. Why the documentation exists but nobody uses it. Why the meeting that was suppose to fix things created three new problems.

I’ve spent my career in that space. I’ve implemented enterprise systems for over a thousand users, watched carefully designed processes go unused the moment they launched, and sat in rooms where smart people couldn’t explain how their own work got done. I’ve been the person asked to fix the system and the person stuck inside a system no one could fix.

What I’ve learned is this: the experience of work is, in large part, the experience of navigating systems. Some of those systems are tools. Some are processes. Some are the unwritten rules about how things happen. And most of them were never consciously designed. They accumulated. They inherited assumptions from a pervious era. They optimized for something that no longer matters.

This newsletter is about that. It’s called Working Notes because that’s what it is: notes from the ongoing work of understanding how people make sense of complex systems at work.

I use the world “operational” a lot. It’s a word that tends to get filed under “not my department”, something for the ops team, the back office, the people who keep the lights on. But operational thinking is how work happens. It’s the layer between strategy and execution, between intention and outcome. It’s where things break. And it’s where, if you look carefully, you can see what an organization believes. Not what it says it believes, but what its systems reveal.

I’m interested in that gap. The gap between the tool and the behavior it produces. The gap between the documentation and the decision. The gap between what we designed and what we got.

I’m writing this for operators, founders, and anyone who has ever been handed a process and thought, this doesn’t work, and I’m not sure anyone knows why. I’m writing for people who care about the craft of making work work. Not in the productivity-hack sense, but in the sense of designing systems that respect the people inside them.

I don’t have all the answers. I’m not sure anyone does. But I’m interested in the questions, and I suspect you might be too.

Welcome to Working Notes.

Next: When Careers Stop Being Paths and Start Being Projects, an exploration of how the traditional career model broke down and what it now asks of the individual.