Fundraising is yucky.

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It was nearly the end of the fiscal year at the nonprofit where I worked – like, the day before the final day of the final quarter. We still hadn’t received one big gift, though the donor had long ago promised he’d come through. As I looked at our spreadsheets that summer morning, I realized that gift was the difference between making our (publicized everywhere) fundraising goal and missing it.

I’d called the donor several times already, and though he was unfailingly polite, I knew I was getting to be a pest.

I could send another email, which I knew he wouldn’t read. He wasn’t an email kind of guy, and of course he didn’t text. At least with me.

Sometimes he just got busy and forgot to send us the check. It had happened before.

I could feel a knot forming in my stomach. What to do?

I’m remembering this story – and feeling slightly nauseous as I think of it – because I’ve been thinking a lot recently of how sometimes fundraising is yucky.

You have to risk hearing the word NO, or, perhaps worse, you have to risk being seen as an annoying pest. It’s hard not to overthink a request for a gift, especially a big one. It can all seem so personal – what if the donor doesn’t really care as much about my work as I thought? What if I’m asking too much? What if … what if … what if?

That’s why I was comforted, as I often am, by what I read this morning from Joan Garry, a national nonprofit guru who has forgotten more than I'll ever know about fundraising. (Want to learn more of what Joan knows? She has a great new book out -- I'm underlining on every page.)

I was looking for tips about how to help a reluctant fundraiser get more comfortable with asking for big gifts. She's already a great storyteller for her organization, and she's getting more help with research. Setting goals and figuring out how to carve out time is coming along, too. It's a great, young organization doing important work. The future is bright.

The truth of the matter is, though, sometimes you just have to do what you have to do: You have to ask. Clearly, politely, thankfully. Sometimes repeatedly. 

Which is what I finally decided to do with my big donor. I called him that day -- twice, I think -- and finally got him on the phone. He told me he was happy to write the check, but he'd put it in the mail.

"No need," I said, and jumped in my car to drive over and pick it up. 

Goal achieved. Lesson learned.