Leading From the Middle: The Pain Points Every Nonprofit Executive Director Knows Too Well

I lived between two worlds: a board focused on strategy and governance, and a staff focused on operations and outcomes. Aligning those perspectives and keeping everyone moving toward a shared vision rested squarely on my shoulders. I was constantly translating big-picture goals into actionable plans, all while trying to keep morale high and navigating the politics that surfaced when vision and reality didn’t quite align. Setting boundaries, maintaining transparency, and protecting organizational integrity often felt like walking a tightrope every single day.

Fundraising wasn’t just a part of my job; it often defined it. Whether I was writing grants, cultivating donors, or managing limited budgets, the pressure to sustain funding never stopped. Every decision felt consequential, every shortfall personal. I cared deeply about the mission, which made financial stress even more acute. Keeping programs alive while maintaining quality and growth often felt like spinning plates and dropping even one felt unacceptable.

I led a team of people who cared just as much as I did, and that passion was both a gift and a vulnerability. Nonprofit work attracts deeply committed professionals, but limited resources and highly emotional missions wear even the strongest teams thin. As Executive Director, I absorbed the stress, the disappointment, and the burden of keeping everyone motivated. I was managing human needs on both sides, my staff and my board, often leaving little room for my own needs.

I chose to take on the position of Executive Director to make a difference, and I did every single day. But the constant demands of leading through scarcity, advocating for change, and carrying organizational responsibility took a toll. It was hard to pour from an empty cup. Over time, compassion fatigue and burnout quietly crept in, even for the most dedicated leaders, including me.

Few people truly understand what it’s like to sit in that seat. You can’t always be fully transparent with your staff, and your board may not be a space for vulnerability.

The world we live in is small. While you may connect with peers and other Executive Directors in your community, they often know your board or team members, making it difficult to be completely honest. The result? Many Executive Directors carry their challenges in silence even as they guide others through theirs.

But you do not have to do it alone. To find out about the Serendipity Executive Director Network,

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