She didn't use the word lonely at first.
She talked about her colleagues. Smart people, committed people, people who showed up. But she couldn't find anyone willing to slow down and dig into the harder questions — not just what are we doing, but whether what we're doing is actually working, and whether we could be doing something that matters more.
I said that sounds frustrating.
She said it was really effing frustrating.
I said: that must make you feel pretty alone.
She paused. Then: yes. I am alone.
She was on a video call. With a small group of her closest allies.
I've been thinking about that conversation a lot. Partly because loneliness has been showing up in other places lately.
I travel a fair amount for work. Airport, gate, seat, hotel room. Something has shifted out there. Earbuds in before anyone sits down. Eyes on the phone. I used to have real conversations on planes — the kind that surprised you, that went somewhere neither person planned. That's mostly gone now. We sit inches apart and stay completely to ourselves.
I noticed the same thing in the minyan I joined after my father died. Same people, same mornings, same prayers, two years running. Good people. But most mornings we moved through the service alongside each other without really being with each other. We were standing before — whatever name you give to that Force Beyond Self — and doing it essentially alone, side by side.
There's something specifically painful about that kind of loneliness. The kind where the people are right there. The meeting is happening. The community exists. And still.
When that CEO said "I am alone," she wasn't describing an empty calendar. She had colleagues who cared. What she didn't have were colleagues who would slow down long enough to ask whether the organization was building what it set out to build, and whether how they operated every day was actually connected to that. She was carrying those questions alone, in her head, every day.
That's an execution problem. And it's more common than the sector wants to admit.
The pattern is recognizable. The leader is smart, mission-driven, and exhausted. They've built something real. And they can't figure out why it keeps demanding so much of them.
They usually call it a people problem. Wrong team. Not enough capacity. Staff who won't take initiative, or won't make a decision without checking first.
Sometimes that's true. More often, what looks like a people problem is something else entirely. The organization hasn't built the systems that would let people operate without the leader's constant involvement. So the leader becomes the system. And systems don't have thinking partners. Systems just run.
I ask leadership teams a question: who in this organization is the load-bearing wall? You know the load-bearing wall — it's the one holding everything else up. Remove it, and the structure comes down with it. In most nonprofits, that wall is the executive director. Take them out of the picture for two weeks and watch what stops moving.
An organization that depends on one person that completely will keep that person indispensable long past the point where it's good for anyone, including them.
And over time, that's exactly what produces the loneliness that CEO described. When you are the system, you can't think alongside it. You can't be in real dialogue with it. The organization lives in your head because that's the only place it fully exists. You carry it largely alone because no one else has the whole picture, and no one else has the tools to hold it with you.
That's a structural problem, and it has a structural solution.
A recent study of 30 nonprofit organizations put some numbers to this. The two most common pain points were too many priorities at once, named by 67% of leaders, and over-reliance on key individuals, named by 57%. Both trace back to the same place: organizations without a clear way to set priorities, track them, and distribute ownership end up loading everything onto whoever has the most energy and persistence. In most nonprofits, that's the executive director.
The two least common pain points were lack of direction and unclear roles. These leaders know what they're for. What they can't do is translate that into consistent action without running it through themselves first.
Knowing what you're for and being able to act on it consistently are two different things. That's the execution problem. And it is also the loneliness problem.
When an organization builds what it's been missing — a regular rhythm for how the team works, a real process for setting and revisiting priorities, clear ownership of who decides what — something changes for the leader that doesn't show up on any efficiency metric.
They get thinking partners.
The structure creates conditions for shared thinking that hadn't existed before, among the same people who were already there. When the work lives somewhere outside the leader's head, others can engage with it, push back on it, take real ownership of pieces of it. The leader stops being the load-bearing wall and starts being the person who designed the structure and can now have an honest conversation about whether it's working.
I've watched this happen. The loneliness that comes with the chair doesn't disappear entirely — there's a weight that stays. But the specific loneliness of having no one to think with? That one is solvable. It just requires building something first.
That CEO leads a $50 million organization built to strengthen community and lift lives. She is good at her work. She is surrounded by people who care deeply about it.
And she is alone.
That contradiction is worth reflecting on. Organizations built to create belonging can become, for the person leading them, among the loneliest places to stand. That happens when the work of building community lives entirely inside one person, because nothing exists to hold it anywhere else.
Start with one question: does your team have a real process for setting and revisiting priorities, or do priorities emerge from whoever pushes hardest?
Most leaders can answer that in thirty seconds. What they find in that answer is usually where the work begins.
And where the loneliness starts to lift.