We were sharing in a post last week about the new AdmittingFailure.com website, the nonprofit equivalent of the confessional booth. The confessions there have prompted me to bare my own soul and share with you my own worst fundraising gaffe.

My lowest moment actually became a turning point, as I think happens to so many nonprofit execs.

It happened years ago when I was still practicing traditional transactional fundraising while serving as President of the Los Angeles Mission. We had a huge direct mail file, and we used to do wealth identifier screening and such. The screening turned up a guy who was a big wheel on Wilshire Avenue–classic major donor prospect.

So I started doing all the tried ‘n’ true moves management moves with this guy, and everything was going great–or so I thought. I ultimately scored an invitation to visit his office. I went in ready to bag my prey.

Then the guy said to me. “I know why you’re here, why you’ve been calling, why you’ve been sending me stuff, why you’re always so nice to me. It’s because you’ve done research, and you know exactly how much money I’m capable of giving to you. And your friendship is totally predicated on that.”

Er…

I had been truly pantsed. I felt naked. The guy was absolutely right. I was at a loss for words. All I knew was that now was not the right time to bust out the calendar and CD I had brought to give him.

“OK, you got me,” I said, slumping back into my chair. “But if you knew that was the gig, why did you invite me here?”

“Because you run the largest rescue mission in the world,” he said. “So I figure that means you ought to know more than I do about how to deal with homeless people.”

He then went on to explain how every day he passed hoards of homeless people on his way to work, on the freeway, on the way home, and at the gas station. He said he was happy to give money to the mission, but that still didn’t help him to be able to know how to interact with the homeless people he saw in his own life daily.

That conversation led ultimately to a lively brainstorming meeting–one that I hardly could have expected given the way our meeting had started. Instead of talking about ways that he could support the mission, we talked about ways the mission could support him as he sought to help the homeless people he encountered in his sphere of influence.

It was a seminal point in my growth in thinking as a fundraiser: Stop trying to get people to support you and instead find ways to support them as they tackle the cause in their own sphere of influence. Ultimately that approach is the best (and most genuine and appreciated) “move” we can make with a donor.

And ultimately that approach led to two books, the teaching ministry I now help to lead, and the blog you are now reading.

This means that if you use the comment space below to share your own worst failure—even the quicksand pit that may be slurping you up at present—you may be well on your way to your own career turning point as well.

Enter the confessional by leaving a reply below.

For further inspiration to bare your soul, make sure to check out Allison Jones’ own post, The Best and Worst Moments of My Nonprofit Career. My own story is there, along with those of several other similarly humbled colleagues.