5 min read

For every fundraising professional, failure is inevitable—and surmountable, and even beneficial. To mature as a fundraiser, you should see disappointment as an opportunity to grow.

If there’s one thing I know how to do, it’s how to lose—and not just on trivial things. I have a knack for losing big! Recently, I was inspired by this guy to come up with my own Curriculum Vitae of Failures, and there were some doozies from college on there. From least to most painful: going stag to homecoming my junior year, getting a BIG FAT D in one of my economics courses, and losing the college football National Championship (the biggest game on the biggest stage!).

But now that I’m a development professional, I’ll never have to add another item to that CV, right? Wrong! Turns out, I didn’t leave failing behind on the field after the National Championship loss. Especially when I was first getting my feet under me as a development professional, I felt crushing disappointment repeatedly. Let me relate three examples—and the valuable lessons I learned from them.

Early on in my career, my boss tagged along on a donor trip with me. Perfect, my chance to shine! Not only could I close a massive gift, I could do it in front of leadership and earn some style points. Like a trained orator, I pitched my organization like it ain’t never been pitched before. It was awesome . . . or so I thought. Turns out, I hadn’t sold the donor on my organization’s mission. I had only sold one person—myself.

I’d failed in front of my boss when I’d hoped to wow him. It was pretty crushing, but there was a lesson to be learned: I needed to listen to donors, not just the sound of my own voice. And the bigger lesson, which I might not have seen at the time? Failure happens for a reason. It’s not fun, but if you nail down why it happened, it can provide a great opportunity to grow.

Shortly after that trip, I managed to set a meeting with one of the wealthiest oil executives in Houston. We were having a great conversation, I felt him warming to our mission, and my boss was just about to go in for a $75k initial gift request . . . when I shifted the conversation back to fishing. My boss (deservedly) reprimanded me after, but I thought, “Not a problem, I’ll get back in front of him.” I never did.

The moral of the story for me: Make a plan for visits with major donors, especially ultra-high-net-worth ones. Those visits are too big to mess up, and you might have only one shot.  

These were two major hits in quick succession, and I was reeling a little. But the benefit of the one-two punch was that I got a one-two shot of learning about how to be a better fundraiser. Another axiom that’s easier to say than it is to swallow: The faster you fail, the faster you learn. If those donors had written a check despite my mistakes, I wouldn’t have realized I needed to fix them.

I’m not going to lie, this last example still gets to me. My org’s CFO introduced me to a vendor who, when I met with him, made a commitment for a three-year pledge. I spent the next three years actively stewarding this donor, but he only responded to my emails if an executive was on the thread. Year three came, I was tasked with driving for another gift, and what do you know, he ignored me. He finally agreed to meet with the VP of Development, then proceeded to ignore my follow-up calls until I copied the VP on an email. Five minutes later, my phone rang, and next thing you know he was unloading on me with vicious personal criticism. It got so bad I told him I had to hang up, and he shot back, “You are by far the worst development professional I have ever met.”

Yeah . . . that hurt.

But painful (and insulting) as it was, it also taught me an important lesson about fundraising: People are who they are 100% of the time. Just like in regular life, not everyone is going to be reasonable and friendly. Sure, people can be loving and generous, but they can also be mean and stingy. As a fundraiser, you have to be able to roll with the punches.

SIDE BAR: You might be asking for money, but that doesn’t mean you should let people walk all over you. You’re inviting others to give, but you’re not a beggar. Sometimes, people (like the vendor/donor above) will cross the line, and you’ll have to remind them that you have inherent dignity. If they have a problem with that, send them my way.

But above all else, people are fallible. It’s true of you and me, and it’s true of donors. What does that mean in practice? Sometimes you will do everything right, and the donor will still say no. You can keep growing and getting better in your career, but sometimes the decision will be out of your hands.

Sometimes I’ve failed despite making no mistakes, and often I’ve ended up disappointed because I’ve slipped up (I’m fallible too!). After the three encounters above, I was upset or frustrated or mad. But those tough situations gave me something important: They gave me grit. They made me a stronger, wiser development professional. They taught me how to communicate with donors in a way that they would hear, and how to identify times when I had to be on my guard. And they prepared me to connect with others who are brave enough to keep the torch of fundraising excellence aloft.

Okay, I’ve talked a whole lot about failure, but here’s maybe the most important thing to remember as a fundraiser: The good times will outweigh the bad. For all my failures—and there have been plenty of them—I’ve seen more moments of success. 

I’ve secured multiple $100k, $250k, and larger gifts. I’ve met with budding philanthropists who made splashes with introductory gifts that blew me away. I’ve visited with donors who have inspired me to be a better man, husband, and father. Donors have shared how they made their gift in honor of their daughter who passed from a skiing accident. One donor called to tell me he was challenged by one of my questions and realized that “he gave as an afterthought, and had never given to the point that it was memorable to him.” So he gave $750k to an organization in his hometown that needed to secure a leadership gift to their campaign. And I’ve had donors sign over a portion of their estate to our organization and cry because they’re so moved at the significance and beauty of gifting their legacy.

And you know what? I never would have experienced those incredibly fun, moving, joyful moments had I not pushed through the disappointment. Without weathering the failures, you don’t get to enjoy the moments of success.

So here’s to failing fast, and growing in your career! Remember, however bad these situations might make you feel, they ultimately support the mission you represent. And the people you impact may not know it or say it, but they’re grateful. If they don’t say it, call me—I’ll give you a much-deserved thanks!

A final update: I didn’t stay a loser with bad grades. Miracles happen, and I’m married to a beautiful woman, have four kids, and achieved a 4.0 in my MBA program (kids and all!). As far as physical and athletic achievements in my post-football life . . . those I’m still working on.

Leave a Reply

Your email address will not be published. Required fields are marked *