Since the beginning of time, we’ve been wired to avoid risks because that’s how we survive. But while this instinct may protect us from danger, it also holds us back. Success requires bold, unconventional actions that often draw criticism. Businesses understand this well, but nonprofits often struggle to embrace it.
Whether you’re preparing year-end appeals, planning outreach to major donors, or focusing on planned giving opportunities, a thoughtful approach can make all the difference for your nonprofit. If you’re feeling overwhelmed, take a deep breath and grab a list—or make one! Because the key to a successful year-end campaign is as much about preparation as it is about execution.
Note how often the tone of instructive materials treats fundraising as something we do to prospective givers, not what we do with potential partners.
Stories are humanity’s secret superpower—they connect us, move us, and even make us cry over a stranger’s triumph or a puppy’s soulful eyes. They simplify life’s chaos, turning cold, hard facts into warm, relatable moments that stick with us. Great stories aren’t just told—they’re felt. In marketing, they sell transformations, and in philanthropy they tug heartstrings. The key? Simple, real, meaningful, even with a sprinkle of humor—who doesn’t love a hero who trips over their cape? The best stories don’t just inform; they inspire, leaving your audience ready to act… and maybe even laugh through their tears.
Asking for a contribution makes most people nervous, which causes rambling,” says Lori L. Jacobwith of Ignited Fundraising. “And together, we have the perfect storm to make the most common fundraising mistake: talking too much.”
Luckily, the most important lessons I’ve learned in my 40+ years of fundraising and charitable estate planning came near the beginning. Many of those experiences were painful, and it’s still somewhat embarrassing to shine a spotlight on my greatest mistakes. Nonetheless, things I learned from my stumblings have become essential elements of my fundraising career. Here are my top ten greatest mistakes (so far).
When you think about donating to charity, what comes to mind? Most of us picture generosity and kindness—people stepping up to make the world a better place. But behind every gift lies a complex system of tax benefits, sparking plenty of debates. And some are ugly.
Predicting the future of philanthropy is a tricky business—and even more so when it comes to political shifts. Under the new Trump administration, the direction of philanthropy could change, although I do not think it will drastically. We can only take some guesses based on historical data and recent events.
Philanthropy, by nature, carries an air of generosity and goodwill — a way for the wealthy to give back and help address big societal challenges. And let’s be honest, most of us admire the idea of someone using their resources to make the world a better place. But not everyone sees it that way. Critics argue that large-scale philanthropy can sometimes do more harm than good, creating power imbalances that let the rich call the shots. It’s a tricky topic.
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