Living Beyond the Limits of Grant Game
"If it was a snake it would have bitten you."
For many nonprofit leaders, the idea of financial sustainability feels like a distant goal — something to revisit once the next grant cycle is secured or the next government contract renewed. But what if the path to real sustainability has been closer than we think, and the main thing standing in our way is our own imagination?
I believe the first few steps for organizations looking to move beyond reliance on grants and government contracts are to secure the buy-in of the board and executive director in what is possible with a major gift strategy — significant-sized checks (whatever that may mean for one’s organization) that come from relationship-based donor cultivation and solicitation.
This is not a radical idea. It is, in fact, one of the oldest forms of philanthropy. Long before grant applications and government contracts existed, communities were built and sustained by people of means who believed in a cause and chose to invest in it. The question is: why have so many of us in the nonprofit sector — particularly those of us serving communities that have been historically under-resourced — convinced ourselves that this kind of giving is not available to us?
The Proximity We Overlook
Many of us — certainly not all — live in proximity to affluent communities, relatively speaking, with access to local wealth. A small business owner who grew up in your neighborhood and made out well. A retired firefighter who attends your community events. The librarian who inherited a sizable family estate. A mid-level tech employee who has been quietly looking for somewhere meaningful to put her charitable dollars. These individuals exist in our circles more often than we recognize.
Yet many organizational leaders struggle to imagine that someone would want to give a 5- or 6-figure gift to their organization without expecting some type of nefarious exchange. This skepticism doesn’t come from nowhere — it is rooted in generations of exploitation and broken promises made to marginalized communities by wealthy institutions and individuals. That history is real, and it deserves to be named.
The Mindset Shift
But here is where we have to be careful: allowing that historical pain to become a blanket assumption about every person with financial means does not protect our communities. It limits them.
Especially with the current elitist and xenophobic behaviors of our nation’s wealthiest individuals, it has been easy to assume that all people with disposable income capable of significant giving share those same worldviews. But that is not only false — it is antithetical to building a culture of philanthropy, and it is actively inhibiting our growth and the communities we serve.
Consider this scenario: a program director at a local nonprofit spent years turning down invitations to speak at community luncheons, assuming the attendees — mostly business owners and retirees — wouldn’t connect with the work. When she finally accepted one invitation, she was approached afterward by a woman who had grown up in the same neighborhood the nonprofit served. That woman became one of the organization’s first $10,000 donors. Not because she was solicited with a polished pitch — but because she finally heard the story and felt seen in it.
That story is not unique. It plays out in communities across the country when nonprofit leaders allow themselves to share their vision beyond their immediate circles.
Walk in Possibility
The shift I’m calling for is not about chasing wealthy donors at the expense of your values. It’s about expanding who you believe deserves to hear your mission — and trusting that the right people, when they hear it, will want to be part of it.
This requires us to move in a less insular fashion and make a habit of sharing our vision with our broader community. It means attending events outside of the nonprofit bubble. It means board members having honest conversations with people in their networks about the work their organization does. It means an executive director being willing to have a cup of coffee with someone they’ve never met, simply to share what they’re building.
It means activating a vision for what becomes possible when we seek out people with material means who genuinely want to be part of our mission — not extractive partners, not grant-makers setting conditions, but people who believe in what we are doing and want to support it.
Making in Real, Though
None of this works without internal alignment first. If a board member privately believes no one would give $25,000 to “an organization like ours,” that belief will quietly undermine every major gift conversation before it begins. Securing buy-in means having direct, honest conversations with your leadership about what is actually possible — and what assumptions need to be challenged to get there.
It means investing time in relationship-building before any ask is ever made. It means tracking donor cultivation the same way you track program outcomes. And it means celebrating early wins — even a first $2,500 gift from a relationship someone on staff built over six months — as proof that the strategy works.
The resources our communities deserve are not locked inside government contracts or foundation coffers alone. Some of them are sitting right next to us, waiting for someone to finally extend the invitation.
Venable Foundation - Funding for civic, art, legal, health organizations across 8 major metro areas. LOI approval is required before applying. - September 1, 2026
Park Foundation - Grants for civic participation, media, environment, and school food for organizations across the country - July 7, 2026
Looking Out Foundation - Funding for immigrant & refugee work, trans and gender-expansive people’s rights, and access to mental health services - July 1, 2026
Juliet Ashby Hillman Foundation - Funding for nonprofit programs in Portland, OR - July 1, 2026
Trust for Civic Life - Civic Hub Grant - grants provide flexible funding for local groups in our priority regions- July 2026
Allianz Foundation - Professional and personal growth experiences for youth 16-25 in select major metro areas across the US - June 30, 2026
The Franklin P. and Arthur W. Perdue Foundation - Funding requests for nonprofit organizations near their operating facilities across the US - June 30, 2026
Goodwin Family Memorial Trust - Grants for organizations serving boys and young men in need in Southern California - June 30, 2026
Del E. Webb Foundation - Grants for nonprofit organizations with offices in Arizona, Nevada, or California, that provide services to their local communities - June 16, 2026
Leadership Fellows at The Trust - rolling deadline
Harvard Health Coverage Fellowship - rolling deadline
Seeding Disruption Fellowship - rolling deadline
Craft Archive Fellowship - For researchers, scholars, and artists conducting research on history of underrepresented craft artists - - rolling deadline
Women inPower Fellowship - For women who are 3-5 years away from C-suite positions or women based in NYC (separate cohorts) - November 2026
Loghaven Artist Residency - Artists across mediums get support and a stipend during a residency in the Tennessee woods - July 15, 2026
Just Tech Fellowship - supports researchers, artists, and practitioners addressing how technology shapes society and public life - June 28, 2026
Working Assumptions Project - For artists depicting what family does and can look like, using still photography as a primary medium - June 1, 2026
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