The Loneliest Desk in the Building
What every new executive director needs to hear but nobody says out loud
I was thirty years old.
Five-story building. Dozens of staff. A mission I believed in with everything I had. And I sat at my desk at a homeless shelter in North Dakota feeling completely, utterly alone.
Nobody told me it would feel like this.
Nobody warned me that the executive director’s desk — no matter how full the building is — is the loneliest seat in the house.
I knew there was something I was supposed to be doing. I just didn’t know what it was.
I didn’t know to build a donor call list. I didn’t know to do structured vision work with my staff. I hadn’t found the right mentors yet. I hadn’t found the coaches who would eventually help me see what I couldn’t see from where I was sitting.
I just sat there. Carrying it. Alone.
If you’re a new executive director, this post is for you.
Nobody Says This Out Loud
Recently I had a conversation with a new ED who came to the role from a career in accounting. He saw a need. He got pulled in. He described it the way a lot of EDs describe it — the quicksand happened — and suddenly he was running an organization.
He shared three things that stopped me in my tracks. Not because they were surprising. Because they were so honest.
One. There are so many things only the executive director can do.
Board relationships. Finances. Fundraising. The things that can’t be handed off, delegated, or outsourced. They live on your desk. They wait for you. And when you’re new, you don’t always know what they are until you’re already underwater.
Two. Fundraising never stops.
Not when you’re tired. Not when the program is struggling. Not at Christmas. Not in summer. Not ever. The ask is always out there waiting to be made, the donor relationship always needing to be tended, the gap between budget and reality always needing to be closed.
Three. Sometimes being the leader is just exhausting.
He said it plainly. And I appreciated him for it. The fight against burnout is real — I’ve been in that fight personally — and most leaders won’t say it out loud because they’re afraid it makes them look weak. It doesn’t. It makes them human.
Here’s the Fourth Thing Nobody Says
I’d add one more to his list.
Telling the story never stops either.
You tell it to staff. To your board. To volunteers. To donors. To the community. You tell it on good days when momentum is high and the wins are visible. You tell it on hard days when the numbers are soft and the mission feels heavy.
And when you tell it well — when you genuinely invite people into the work, when you help them see what God is doing and get excited about partnering with it — the dollars follow. That part is real.
But here’s what nobody tells you: sometimes the hardest person to tell the story to is yourself.
Keeping your own faith that the resources will come. That the mission is worth it. That the exhaustion has a purpose. That the loneliness at that desk is not the whole story. That can be the heaviest lift of all.
The Weight Nobody Prepared You For
Here’s the tension every ED lives in.
You’re doing all of the above — board, fundraising, story, finances, relationships — while simultaneously developing your systems, developing your staff, being the chief cheerleader, and being the chief problem solver.
That is a heavy load.
And without systems underneath it, everything stays on you. The fundraising. The vision. The operations. All of it. Which makes sustainable growth nearly impossible and accelerates the burnout that’s already knocking at the door.
I know because I lived it. Thirty years old. Five floors of people counting on me. No roadmap. No system. No one who had sat in that chair and could tell me what the chair actually required.
It took time to find the right mentors. The right coaches. The people who had been where I was and could help me see a way through.
Not every new ED has that.
And that gap — between the loneliness of the desk and the community and clarity that could change everything — is exactly why Bold Leading exists.
You Don’t Have to Figure This Out Alone
The Bold Bulletin is a free resource for nonprofit leaders who want the frameworks, insights, and honest conversation that nobody handed them when they sat down at that desk. Practical leadership. Faith-grounded perspective. No fluff.
If you’re a new ED — or if you lead one, love one, or are trying to become one — this is for you.
👉 Subscribe to The Bold Bulletin at blog.boldleading.com
You don’t have to figure this out from a lonely desk.
Dave Sena is an ordained minister and the founder of Bold Leading. After 25+ years leading and consulting with nonprofit organizations, his mission is simple: help Gospel-centered leaders build the teams and systems they need to serve with excellence — without burning out.
Learn more at BoldLeading.com — or reach out directly at dave@boldleading.com.