Good morning, CharterFolk.
Today we are pleased to present a Contributor Column from Chris D’Amato, the COO at Matter Real Estate.
We provide a bio for Chris below.
Chris D’Amato is Chief Operating Officer of Matter Real Estate, an owner’s representative and advisory firm serving charter schools and mission-driven organizations. He began his career as a special education teacher and spent more than fifteen years in charter school operations, most recently leading facilities expansion at Zeta Schools in New York City. In his current work, he helps schools navigate the real estate, facilities, construction, and vendor challenges that too often fall on operators already carrying more than enough.
The Box I Couldn’t Check
A few weeks ago I was registering for a charter school conference. Name, organization, role. Then a dropdown menu: What best describes you? Operator. Teacher. School Leader. Board Member. Advocate.
I sat there longer than I should have.
I’ve been a teacher. I’ve been a school leader. I’ve opened school buildings. I’ve been the last one in them at night. I’ve managed vendors, compliance crises, facilities hanging on by a thread. I’ve been the person on the other end of the phone when a pipe bursts in a school building at 9pm and there is no one else to call. For the better part of fifteen years I was somewhere in the first three categories on that list without ever having to think about it.
But that was then. So I did what any reasonable person does when they don’t know who they are anymore.
I asked Claude.
Am I an advocate?
Yes, it told me – immediately and without hesitation.
I checked the box. It lingered in my mind for days afterwards.
I’m 10 months out from working directly in schools. The weight is still the first thing I reach for when I try to explain what working inside schools actually is. Not the mission, not the outcomes, not the data — the weight. The raccoon discovered in the building fifteen minutes before student arrival. The unexpected safety situation that completely changes the direction and energy of the next 48 hours of your life (and the lives of so many others). The first day that comes whether you’re ready or not. The accumulated ordinary yet extraordinary things that are yours to carry.
It’s hard to articulate, but the people doing this work know what I’m talking about. The point is that it accumulates, and it’s yours, and you don’t leave it at the building when you go home at night.
Over time I realized I could carry it — that I was built to carry it in my own way that not everyone is. And I left anyway. Not because it broke me, but because I could finally see it clearly enough to know it would, at this stage in my life. That’s a different thing, and I want to be honest about that.
The people still in the buildings definitely don’t need my admiration. But I want to say it anyway because I’m not sure it gets said clearly enough in the rooms where I now spend a lot of my time: what school operators carry every single day is something the rest of this sector does not fully reckon with.
Not the funders, not the board members, not the policy people, and honestly not most of the vendors — including me on my worst days. There is a version of this work that happens at a comfortable distance from consequence. Where the thing that goes wrong becomes a lesson learned for the future. Where you can close your laptop at 6pm and genuinely stop thinking about it.
The people still in the buildings cannot do that. They carry that in a way I recognize, and also a way I no longer fully share — and I think sitting with that honestly is more useful than pretending the distance doesn’t exist.
What I want my work to be now is this: the person who can reach back into that building and actually lift something. Not narrate the problem. Not write a report about it. Take something off the pile that never really should have been the school’s to carry alone — the lease negotiation, the facilities project, the landlord conversation, the architect or contractor or vendor relationship that quietly eats up hours no one has. The work I do now sits in that space: between the school and the building, between the mission and the very practical realities that can either support it or make it harder.
At its best, that work gives school leaders back some measure of time, clarity, and control. It helps translate the language of real estate, facilities, construction, and ownership into decisions schools can actually make. It does not make the weight disappear. But sometimes it can make one part of it lighter.
That’s the version of this that feels meaningful to me.
Which brings me back to the word advocate.
I’ve noticed it used quite a bit since that day with the checkbox. But advocates don’t send invoices. What most of us are — what I am — is a vendor who cares deeply about the outcome. That’s not nothing. The caring is real, the need and expertise are real, and the work matters to schools that don’t have the capacity to do it themselves.
But it’s not advocacy. Calling it that is a way of borrowing moral weight from the people in the buildings without carrying any of it. It’s the sector’s way of making everyone in the support ecosystem feel like they’re inside the mission rather than alongside it. And that blurring makes me uncomfortable — especially in rooms full of vendors where everyone seems equally certain they’re part of the mission, and nobody is asking whether they’ve ever actually felt its weight.
I’d rather be honest about what I am. Someone who used to do the work and now tries really hard to help people who do.
If you’re a school operator reading this, here’s the only practical thing I’ll offer. When you’re evaluating who to bring in to support your work, ask them about their experience in schools. Not what they know about schools or supporting schools — what it felt like. The vendors worth trusting are the ones who hesitate before answering. Not because they don’t have a response, but because the honest answer is complicated and they know it. There’s also a category of vendor who will tell you plainly that they haven’t carried it — and if they have the humility to know their place in it, that honesty is worth something too in my mind. What you’re looking for, either way, is someone who isn’t pretending.
I’m 10 months out and the last thing I have is a clean resolution to this. The one thing I feel confident saying is that advisory work is nowhere near the same as being inside a school. I made this transition deliberately, and I think it was right — not in some abstract professional sense, but for where I am in my life and for my family. The weight I used to carry home didn’t stay at work. It came through the door with me. Maybe that means I wasn’t as built for it as I thought. Or maybe built for something and built for it forever are just different things. Either way, at this point in my life, it was time to find a different way to be useful.
I checked the advocate box. And for now I’m just trying to show up in a way that the people still carrying the weight would recognize as honest. It’s not a perfect answer, but it’s my best shot at a genuine one.