A family they'd been supporting for three years had just lost their housing.

The city funding — gone. A resignation, handed to her that morning. Her son's diagnosis, still new enough that she hadn't found the right words for it yet.

She'd been up until 2am editing a grant proposal. The logic was off. She was the only one who could see it.

This was our monthly call. She didn't open with a question or an agenda. She just started talking.

She told me how tired she was. And then she said it the way every ED I've sat with eventually does — not as a complaint, not as a cry for help, just as the most accurate thing she could say:

"It's hard being the one who holds all this together."

I call it loneliness at the top. Most EDs recognize the feeling immediately.

What most don’t see is that the feeling is the same — but the problem isn’t.

This is actually four problems masquerading as one. Each has a different solution. Get it wrong, and the weight doesn’t lift. It just shifts.

The first move isn't solving them. It's hearing which one is yours.

Cognitive Load.
Sounds like: “Why am I the only one who sees how all of this connects?”

You’re not just doing the work — you’re holding the context that lets you see how it all fits together. The history of the funder relationship. The reason that hire didn’t work three years ago. The thing the board doesn’t know yet. No one else carries all of it, because no one else has had to.

When you step away, the org keeps moving. But key connections get missed. Opportunities slip. The things that required your read of the room — they just don’t happen.

Skill Scarcity.
Sounds like: “I shouldn’t be the one doing this — but I’m the only one who knows how.”

This one is sneaky. It doesn’t feel like a problem — it feels like being good at your job. And in a lot of ways, it is. You stepped up when it mattered. You learned things no one else learned. That’s not a character flaw — that’s how you built what you built.

But the team has been watching. And what they’ve learned is that if they wait long enough, you’ll handle it. So it’s you — again — at 2am, finishing something due in the morning. Not because they can’t learn it. Because they’ve never had to. And until something changes, they won’t.

Authority Bottleneck.
Sounds like: “Just check with me first.”

The problem isn’t that decisions come to you. The problem is that there’s no system that says which ones should — and which ones shouldn’t. So everything comes to you. The urgent and the trivial. The strategic and the routine.

Your calendar fills with decisions that aren’t yours to own, and the work that actually needs your mind never gets it. You’re blocked by the absence of a structure that would ensure the right decisions get made even when you’re not in the room.

Visionary Isolation.
Sounds like: “I need a thought partner, not another person who needs me to manage them.”

Everyone around you has a stake in how you see things. Your staff needs your confidence. Your board needs your clarity. Your funders need your vision. Even the EDs you respect most are running organizations that compete with yours for the same dollars (we’re telling the truth here right?).

What you're missing isn't someone to vent to. It's someone who can dream with you and help you figure out how to actually get there. Someone who can take a half-formed idea and sharpen it by offering alternatives and raising concerns that save you from missteps you couldn’t see. Without that person, the dreaming stays small. The hard problems don't get solved. And your best thinking never gets met by another mind at your altitude.

If you’ve recognized yourself in any of these, you’ve probably already tried to fix it.

Here’s why it hasn’t worked.

The expensive hire.

You bring in a #2. Smart. Capable. Years of experience.

Three months in, they’re swamped. Six months in, they’re carrying the same load you were — just from a different chair.

This isn’t a hiring mistake. It’s a structural one. Without redesigning the work first, a deputy doesn’t lift the weight. They inherit it. And now you’re paying two salaries for the same problem with a major burnout risk.

Working harder.

You treat it like a stamina problem. Earlier mornings. Later nights. You tell yourself it’ll ease up after this quarter. After this campaign. After this hire.

It doesn’t.

What you’re pushing against isn’t your effort. It’s the shape of the organization. And every week you push through, you teach your team — and your body — that this is sustainable.

It isn’t.

The hero board member.                                                                                          

You recruit someone strategic. A former CEO. A respected funder. Someone who'll finally think with you at your altitude.

They show up to meetings. They give good advice. They go home.

You do share with them. The updates, the wins, the things you're working through. But there's a layer the relationship never quite reaches.

Boards govern. That includes hiring and firing you. Even unspoken, that sets a ceiling on what walks into the room. The hardest questions, the half-formed fears, the what if I'm getting this wrong — those don't go to the people who'll start watching each issue more closely the moment you say them out loud.

Wrong instrument for the problem.

A structural problem demands a structural solution. 

Here is what that looks like for each burden.

Cognitive Load → Get the picture out of your head. Make the connections obvious to your team. Two moves.

First: Document what can be documented — strategy, Theory of Change, decision priorities, annual goals that name the three or four things that actually matter.

Second: Include your directors in the realities you've been carrying alone — the funder signal you caught three years ago, the board chair's hesitation last month, the warning sign on the last hire. Not all at once. As situations come up.

The first gives them a map. The second teaches them how to read it. Do both, and your team starts making connections you didn't know they could.

Skill Scarcity → Upskill your directors through practice, not training. The fix is reps — on the real hard decisions in front of them, every two weeks, alongside someone who can help them see what they're missing. How to show up with funders. How to share your story with the media. How to make sure your programs actually talk to each other. They learn to make nuanced decisions in alignment with what the organization actually needs — not just what's in front of them. Over six months, the work only you could do becomes work two or three of them can carry.

Authority Bottleneck → Build a culture of extreme ownership. Each director owns a defined slice of the work, with clear priorities and annual goals you build together. This keeps them from guessing what success looks like. Then change one expectation: nobody brings you a problem without a recommended solution. By month three, your inbox quiets. By month six, you trust their judgment — because you’ve watched them make twenty decisions well.

Visionary Isolation → Find a thought partner at your altitude, outside your day-to-day structures. Someone whose only stake is your success — and who can get hands-on with the high-level, messy, vulnerable problems you're carrying. Someone who can dream alongside you, sharpen your half-formed ideas, and offer the alternatives or concerns you couldn't see yet. It might be a seasoned ED who's been where you are. A mentor with real sector experience. A fractional strategic partner. The form matters less than the function: consistent, hands-on, free to dream and free to push back.

You didn't get here by accident. The work required more than any one person should carry – so you did. 

The real question is, what could you accomplish if you didn't have to? 

I see you.

Hit reply and tell me which burden is yours. I read everything.

— Durell

More next month.