Why This Gift Planning Director Chose the Messy Middle
Nonprofit leaders are stretched thinner than usual right now. Funding is unpredictable, major donors are harder to land, and the middle of your donor base (the people who could actually sustain you) keeps getting ignored because the ROI feels impossible to justify.
Here’s what most organizations miss: middle donors, those giving between $1,000 and $10,000 annually, represent only 1% of donors but provide 30 to 40% of revenue. Yet research shows that only 8% of organizations even call these donors to thank them. They fall into what fundraising experts call a gray area, too generous for broad campaigns but not quite at the level for major donor treatment.
David Golaner, [https://www.linkedin.com/in/bowtiedg/] Director of Gift Planning at the American Jewish Joint Distribution Committee (JDC), spent 25 years learning that the middle is exactly where you should be investing.
“Middle donors are where the real opportunity lives,” David told me on a recent episode of Notes from the Messy Middle. “The problem is, they require real relationship-building without the immediate ROI that makes it easy to justify. That’s why so many organizations ignore them. But invest in a handful strategically over five years, and you’re building your next generation of major donors.”
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What the Messy Middle Taught Him About Donor Strategy
Now at JDC, David describes his role as being on an “all-star team” where top professionals from various organizations come together. Working globally has taught him that cultural intelligence matters as much as fundraising expertise, and that the world isn’t as broken as media coverage suggests.
His most valuable insight comes from understanding the power of the middle in donor portfolios.
“The middle has the worst ROI compared to mass fundraising or major donor gifts,” David admits. “But it’s also where most organizations underinvest, and it’s messy to manage.” As a middle donor himself, he understands the tension of giving to a large organization where your contribution barely registers versus a small one where the same amount prompts a parade.
His solution? Relevance and impact reporting. Show donors why they matter and what their investment accomplished. Make the case for your organization’s relevance in their lives, whether they’re deeply engaged or only interact occasionally.
This matters right now because so many nonprofits are chasing major gifts while neglecting the donor segment that could sustain them through volatile funding cycles. The middle is messy, but it’s also where stability is built.
When Stepping Back Means Moving Forward
Understanding the power of the middle didn’t come from theory. It came from David living it. After years in executive leadership, he made a move that puzzles most people in our field: he deliberately stepped back into middle management. Not because he had to, but because he wanted to make a bigger impact.
His transition started when the senior center he led in Baltimore merged with a larger organization. Rather than viewing this as a loss, he saw it as an opportunity to scale up his learning. He joined the Associated Jewish Federation of Baltimore in middle management, working on a centennial campaign at an organization with a $50 million annual budget and a $200 million campaign. The nonprofit sector operates differently at scale, and David knew that to expand his impact, he needed to understand how larger systems work, even if it meant a smaller title.
The shift required an identity reset. David had spent four years working for a Jewish funeral home, and he knew that role had started to define how people saw him professionally. So he made a deliberate choice to rebrand himself, right down to changing his wardrobe to wear bow ties as a visual marker of his evolution. “I needed to separate that chapter from what came next,” he explained. “Sometimes you have to actively signal that you’ve moved on.”
He’s in what he calls “the middle of his professional story”, hoping for another 25 years of meaningful work. That perspective, that willingness to embrace the messy middle of his own career, taught him everything he knows about why that same territory matters in fundraising.
While he rebranded his style, his core values remained consistent. When I asked David about those values, he didn’t hesitate: humility, amenability, and curiosity.
“Curiosity is a great value for growth,” he said. “Amenability is just being nice. And humility and amenability together make you someone people want to work with, regardless of their role or level.”
These principles allowed him to step back without ego, to learn from colleagues after decades of leadership, and to adapt when the pandemic forced everyone to pivot from relationship-based, in-person philanthropy to remote donor engagement practically overnight.
For nonprofit professionals navigating funding uncertainty, staff turnover, and donor fatigue, these values are survival skills.
What Nonprofit Leaders Can Learn
David’s insights apply whether you’re rethinking your donor strategy or navigating your own career transition. Here’s what matters most:
1. Diversify your revenue streams beyond traditional fundraising. David’s experience as the first director of auxiliary revenue at the Park School of Baltimore taught him that income from assets like summer camps and facility rentals creates organizational resilience. This makes for “a healthier organization in good days and a viable organization in the not-so-good days.”
2. Invest in your middle donors strategically. Don’t try to steward everyone equally. Pick a handful of middle donors with the right combination of involvement and capacity for growth. Philanthropy is a long game, and developing even a few of these relationships over five years can yield significant returns.
3. Use your donors as a focus group. Ask them directly what type of communication they respond to and what would move them from liking your organization to loving it. David notes the old fundraising adage: “Ask someone their opinion and you’ll get a gift. Ask for a gift and you’ll get an opinion.”
4. Learn to say no so you can say yes to what matters. David’s ability to balance a demanding role with family life and board commitments came down to one skill: prioritizing ruthlessly so he could live up to the expectations that truly mattered.
5. Embrace the fact that there’s no escaping the messy. Whether you’re navigating a career transition or managing a donor portfolio, the middle is inherently complicated. The leaders who succeed are the ones who stop trying to avoid the mess and start learning from it.
David’s journey proves that growth doesn’t always look like climbing the ladder. Sometimes it looks like choosing the bigger pond, even when it means you’re no longer the biggest fish. The most strategic move can look like a step backward to everyone watching from the outside.
You can find David on social media at @bowtiedg, and listen to our full conversation on Notes from the Messy Middle. [https://eringregorycreative.substack.com/podcast]
I believe the life you design on purpose is the one worth living — and the same is true for your organization's story. I'm a brand strategist and storyteller helping mission-driven organizations and entrepreneurs clarify their message and communicate their impact. Learn more at eringregorycreative.com.
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