55 Years of Wisdom: How a Lifetime of Living Has Made Me a Better Fundraiser
Chapter Leadership Brief 10.3.25
by Terry Pearl
Founder & Chief Philanthropy Partner, 360 Philanthropy Partners
Today, I turn 55.
It’s a milestone I approach with a full heart, a clearer head, and—if I’m being honest—a deeper appreciation for the road behind me than ever before. I’ve earned every gray hair, every laugh line, and every quiet moment of insight. And I’ve come to understand that nothing has shaped my work in relationship-driven fundraising more than the wisdom gained over five and a half decades of living.
Fundraising, at its core, is not about tactics. It’s not about scripts, data, or even strategy—though all of those are important. At its best, fundraising is about connection. Human to human. Heart to heart. And nothing sharpens your ability to connect like living fully and paying attention along the way.
So today, in celebration of 55 years, I want to share four timeless lessons that have transformed the way I show up for my donors, my colleagues, our partners, and the causes I care so deeply about.
1. Listening is more powerful than persuasion.
When I was younger, I thought great fundraising came from great pitches. I'd labor over every word, making sure that the ask was airtight. But the older I get, the more I realize: it’s not about what I say. It’s about what I hear.
At 55, I’ve become a better listener—not just to what donors say, but to what they mean, what they’re afraid of, what they hope for, and even what they can’t quite put into words. I’ve learned to listen with curiosity instead of an agenda. That shift alone has opened more doors than any clever campaign ever could.
Donors want to be seen, known, and valued—not just thanked. They want to know you understand what matters to them. And that starts by listening like their story is more important than your proposal. Because it is.
2. Confidence comes from clarity, not control.
In my 30s and 40s, I believed confidence came from having all the answers. Now, I know it comes from something else entirely: clarity of purpose.
I may not control the outcome of every ask. I can’t predict the market or guarantee a campaign’s success. But what I can do—and what I do with increasing conviction—is lead with clarity. Clarity about the mission. About why it matters. About the real impact of the donor’s gift.
When you’re rooted in clarity, you don’t have to control the conversation—you simply have to show up as a trustworthy guide. At 55, I’ve stopped trying to “sell” donors and started inviting them into something meaningful. That’s a much more powerful place to stand.
3. Relationships are built in the in-between moments.
If you’ve been in fundraising long enough, you know this: the best relationships aren’t built in boardrooms or gala dinners. They’re built in handwritten notes. In follow-up calls that don’t include an ask. In moments when you say, “I thought of you,” and mean it.
Over the years, I’ve learned that consistency beats intensity. The fundraiser who shows up again and again—not just when there’s a gift to be made—is the one who earns trust. At 55, I make fewer “asks” and more “check-ins.” I track life events more closely than pledge payments. I treat my donor list less like a database and more like a garden—something to tend, not something to mine.
This isn’t just good fundraising—it’s good humanity.
4. Meaning matters more than metrics.
Don’t get me wrong—I love a good dashboard. I believe in data. I even help fundraisers learn how to track and measure what matters.
But here’s the thing: I’ve seen too many fundraisers obsess over metrics and lose sight of meaning.
At this point in my life, I care less about the number of donors and more about the depth of relationship. I care less about the campaign total and more about the impact that money will make possible. What did giving do for society and the donor?
What made them feel hopeful, powerful, connected?
Because in fundraising, we’re not just raising money—we’re stewarding belief in what’s possible. That’s sacred work. And it deserves a sacred mindset.
Why 55 Is Just the Beginning
If you’d told me 20 years ago that I’d feel more passionate, more effective, and more connected at 55 than I did at 35, I wouldn’t have believed you.
But here I am.
I’m more patient, more intuitive, and more grounded. I don’t chase donors anymore—I meet them. I don’t push myself to “do more”—I focus on doing the right things, the meaningful things.
And that’s the gift of aging in this field: You learn that fundraising isn’t really about money. It’s about meaningful connection. It’s about creating something bigger than yourself, something that will last longer than any campaign ever could.
So on this birthday, I raise a metaphorical glass to all the fundraisers walking this same path. If you’re younger, take heart—your wisdom is coming. If you’re older, keep sharing your stories—we need them. And if you’re right here with me, at the beautiful bend of midlife, then you know:
The longer we live, the more we have to give.
And what a gift that is.
Here’s to 55—and the many lives still waiting to be changed by the power of real connection.
Let’s Stay Connected
Whether you're a fellow fundraiser, a nonprofit leader, or someone who's passionate about advancing nonprofits through meaningful giving—I'd love to connect.
📩 Reach out if this message resonated with you.
🤝 Let's talk about building relationships that matter, fundraising with heart, and leading with wisdom.
💬 You can find me on https://www.linkedin.com/in/terrypearl360pg/ or drop me an email at terry@360philanthropypartners.com
We’re all in this together—and there’s so much more to do, learn, and give.
Here’s to the next chapter.
Terry Pearl is the Founder and Chief Philanthropy Partner of 360 Philanthropy Partners, bringing over 20 years of experience in fundraising strategy, board development, and nonprofit leadership. She has raised more than $200 million for mission-driven organizations, including principal gifts up to $50 million. Terry has advised a wide range of partners—from research institutes to veteran service organizations—and previously held senior roles at NYU Langone, St. Joseph’s Health, and The Headstrong Project. She holds MPA and MBA degrees from the University of Miami and a BA from the University of Pennsylvania. Terry is a passionate advocate for nonprofit growth and sustainability.