The Messy Middle
Why markets stall in transition - and what it takes to build through it.
There’s a moment when it clicks.
You’re in a room - or a call, or a conversation that runs longer than it should - and something shifts. The signals you’ve been collecting start to connect. Customers describing the same friction in different words. Teams building the same workaround independently. Hesitation where there should be momentum. Suddenly the pattern is undeniable and you can’t stop thinking about what comes next.
That feeling is the beginning of something. It’s also the beginning of a very particular kind of work.
There’s a phase every market goes through that nobody names out loud.
The old way still works - mostly. The new way is visible to enough people that the conversations have started, the pilots are happening, the consultants have been hired. But the transition hasn’t completed. The infrastructure that would make the new way obvious and inevitable doesn’t exist yet.
So the market sits in an uncomfortable in-between: acknowledging the need for change while hesitating to fully commit to it.
I call it the messy middle.
I’ve spent over a decade living inside it. And the thing I’ve learned is that the messy middle isn’t a failure of vision. Most markets in transition have plenty of people who can see where things are going. The challenge is more specific: almost nobody can hold the whole system at once - where the market is today, where it needs to go, and what the path between them actually looks like in practice.
That’s the job. Not just seeing it. Carrying it.
In one market I worked in, everyone agreed the process was broken. Teams were still passing documents and spreadsheets back and forth, rebuilding the same context by hand, and relying on institutional knowledge to bridge gaps that should have been solved by infrastructure.
Nobody disagreed on the problem.
The stall came from incentives. Each participant could patch their own pain just enough to function, but no one owned the neutral layer - the shared data, workflow, and trust infrastructure that would reduce friction across the system.
That pattern shows up everywhere.
In product, you become the living proof of concept for a future most people can’t yet fully imagine.
You’re taking in information from every direction: customers who feel the friction but can’t fully articulate the fix, engineers who can build almost anything but need to know what’s worth building, leadership that believes in the destination but needs confidence in the route, and a market full of participants with real stakes in how the transition unfolds.
Nobody else in the room holds all of it. So you hold it.
And you translate it - constantly, in every direction - until enough people can see enough of the system that momentum becomes possible.
What makes that sustainable is the evidence. Not always a spreadsheet. Often it’s qualitative: the same tension surfacing in conversations with customers who don’t know each other, the same workaround appearing independently across different organizations, the same hesitation in rooms where the incentives should be pointing toward yes.
The pattern is consistent enough, confirmed from enough directions, that the signal doesn’t disappear when the room pushes back.
That’s the crucial distinction between a product mistake and a real opportunity.
A product mistake is building something no one actually needs - a problem that exists more in the builder’s head than in the market. This is different. The need is real. You can hear it. You’ve heard it repeatedly, from people with nothing to gain from telling you what you want to hear.
The friction shows up in behavior, in workarounds, in the gap between how things should work and how they actually do.
The question usually isn’t whether the problem is real. It’s whether you’re the right person to fix it - and whether the moment is right.
Sometimes those two things align.
When they do, the responsibility is to move.
This is a publication about that work.
Not about any single market or industry - though I’ll draw on what I know from building inside markets where the messy middle has been especially stubborn. The pattern is portable. Different industry, same phase. Different language, same structural problem underneath.
What does the neutral layer look like when it finally arrives? What gets in the way of building it? What unlocks when it does?
Those are the questions I want to think through in public - with people building inside their own messy middles, investing in companies navigating them, or trying to understand why markets that should have solved certain problems by now still haven’t.
I’m writing because I have things to share that don’t fit neatly anywhere else.
Some of the most useful insights about how markets develop get lost between the people who live them and the people who could benefit from them. And some of what I’ve spent years carrying - the signals, the patterns, the shape of what becomes possible on the other side - is more useful out in the open than held privately.
Sometimes the person best positioned to see a solution is simply the one who has been inside the problem long enough, from enough angles, that the full system becomes visible.
That’s not a special talent. It’s a vantage point.
And a vantage point carries an obligation to share what you can see.
This is where I’ll write about that work: how markets get stuck, how product teams misread signals, and what it takes to build the layer that makes change real.
Building Through Friction is about market infrastructure, product strategy, and systems thinking - across industries where the messy middle is still being navigated.
If this resonated, subscribe. Up next: how to tell whether friction is a timing problem, a trust problem, or a product problem.