You might not know this about me, but I’m a muller. I like time to turn things over in my brain and noodle on what it all means. And that’s what I’ve been doing since I got back from the CAGP’s National Conference a couple of weeks ago.
Since my first time attending in 2019 (when Holly, Fraser and I launched You Can’t Take it With You: The Art and Science of Legacy Fundraising), this gathering has become an annual highlight for me. It’s not just the sessions themselves, although I always come away with learnings. But more than that, the vibes of CAGP are immaculate, and unlike any other nonprofit conference I’ve been to.
This year, I found myself less focused on specific tactics and more drawn to the broader patterns emerging in how we’re thinking about donors, generosity, and the systems that underpin the work we do in this sector. Here’s what’s been sticking with me:
Segmentation isn’t scarcity
Legacy has always gone hand-in-hand with demographics. For years, it was Civics and Boomers. Since COVID, Millennials have become the planned giving darling (and yeah, Gen X, I see you getting overlooked in that mix!).
What I hope we hang onto is that this isn’t an either/or conversation. There are benefits to marketing to Boomers (shorter time to realization, but they give at a lower rate) and to Millennials (who leave gifts in Wills at a greater rate, but have many more years of living likely left ahead of them). One group isn’t better or worse, or more or less valuable or relevant, than the other, and you don’t need to choose one.
In fact, I’d suggest that to focus your program on one, at the expense of the other, is a risk! Choose to focus on Millennials, and you can expect a revenue gap thanks to the longer time to realize, coupled with the lower rate of giving from Boomers. Focus only on Boomers, and you may not make it into the first or second Wills.
Perhaps the real work is building programs flexible enough to honour different generational preferences at the same time – and to observe how preferences evolve with age.
Democratizing DAFs
Donor-advised funds came up frequently, which isn’t surprising. But what struck me was how the conversation has matured in the last few years.
Organizations are moving past treating DAFs as a puzzle to solve and instead weaving them naturally into their broader marketing approach. I’m seeing thoughtful integration—programs that make giving through DAFs feel more accessible and available to donors, and foundations that are collaborating with charities to recognize DAF donors early, communicate with them throughout the year in ways that acknowledge how they give, and genuinely make it easier for them to support the causes they care about. It feels like we’re collectively getting more comfortable with this reality of modern philanthropy.
Scale Is The Word
Charities want to deliver personalized, meaningful legacy journeys, but 90% of them aren’t resourced to do it. We talk about in-person conversations and phone calls. We talk about direct mailings and surveys. Why aren’t we talking more about mass, hybrid programs?
How do charities maintain consistent, meaningful communication with legacy prospects while also knowing when to add those personal, high-touch moments that deepen relationships? It’s not about choosing between mass marketing or in-person touchpoints. It’s about understanding how they work together—the mail that keeps legacy giving present in someone’s mind, and then the handwritten note or intimate gathering or phone conversation that arrives at just the right moment.
Finding that rhythm isn’t straightforward, and I valued how openly people talked about what’s working and what isn’t. When does a personal touch feel genuinely personal versus performative? How do you scale warmth? Which donors want more direct contact, and which ones prefer to engage on their own timeline? These questions don’t have tidy answers.
What I keep coming back to is how these themes connect. Legacy giving has become more complex, and so has the marketing that underpins it. We find ourselves stuck in false dichotomies (mostly driven by capitalist, scarcity mindsets), when the reality is that there’s space for it all – the Boomer and the Millennial, the DAF and the residual gift, the phone call and the mass mailer.
For those of you in the middle of building or rethinking programs right now, I’d love to know what resonates. Where are you feeling this tension between structure and flexibility most acutely?
Charlotte Field is a fundraiser and digital native with more than 15 years of experience in communications and fundraising. She’s a strategic thinker with a mind for integrating offline and online tactics to create cohesive donor journeys that generate exceptional results. As a partner at Good Works, she’s worked with charities of all sizes and causes to raise funds from annual and legacy donors. Charlotte is a co-author of ‘You Can’t Take It With You: The Art & Science of Legacy Fundraising’ (2019), a regular on the conference circuit, and pronounces ‘GIF’ with a hard ‘G’.
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