The Worst Day of My Career: Making It About the Money

“I am truly awesome!”

That’s what I thought on the way back home from a donor meeting after landing the biggest individual contribution in my non-profit's history. I was ecstatic and couldn’t wait to share the news with my organization’s president.

But when I returned to the office, I was greeted by a frustrated face and a devastating question.

“What on earth happened?”

All my joy dried up. What could have gone wrong?

Let me explain.

In my late 20s, I was eager to make my mark on the world. I had just begun as a development director at a small non-profit that trained people with disabilities in computer technology and helped them reach high-paying jobs in the industry. Because this was a small shop, I did a little bit of everything: annual fund appeals, events, grant-writing, major gift cultivation. It was a great opportunity to get some hands-on experience in a variety of areas.

About a month into working there, I had reviewed files on our major donors and made a list of those who hadn’t given in a couple of years. One of the donors on the list was Tom, a dedicated board member whose last gift was three years earlier. I knew he had money and would be a great person to target for a big gift.

With the president’s approval, I called Tom, set up a meeting, and explained that I’d just wanted to get to know him a little better. But on the ride over, all I could think about was asking him for $20,000 and presenting the check to my boss like a white knight.

Initially, Tom took me at my word. He talked on and on about his family, his vacations, and his work. I didn’t pay much attention. I had tunnel vision, and eventually I pounced at the first real pause in the conversation.

“You’ve been a board member for about four years, and I noticed you haven’t given in the last 24 months,” I said. “I’m wondering if you could make a $20,000 gift today?”

He looked jolted, then flustered.

“What?” he said. “Um . . . I don’t . . . wait, hmm . . . yeah, I think I can do that. I might need to move some things around, but I . . . I think that’s doable.”

Success! I quickly shook his hand, thanked him, and floated back into my car as though I’d won the lottery. But the mood was significantly different inside my office. Upon my return, the president waved me into his office and explained that the board member had just called him, totally blindsided, so jarred by my brash ask.

“He’s decided he will not make such a gift. And he just resigned from the board.”

My stomach knotted up. I felt like I would keel over and die.

Luckily, my boss was a compassionate person. He knew my intentions were good. My methods, on the other hand? There was plenty of room for improvement. Ultimately, things got better. After a little time, I was able to issue an apology to Tom, he eventually came back to the board, and he did give us that $20,000 check. It was an undeserved happy ending.

Looking back, that was the worst day of my professional career, but I learned so much from it. I had ignored just about every principle of donor relations. Here’s what went wrong:

• I went after the money, not the relationship. I was thinking only about bringing back that check instead of developing a friendship with the donor.
• I didn’t do my research. Had I done more investigating, I would have known that Tom had started a new business two years earlier and was struggling financially.
• I didn’t listen. Tom was trying to tell me who he was and what he cared about, but all I could think about was how to make the big ask.
• I had no plan. I hadn’t thought about where I wanted to go with Tom or any other major donor. I just was going to charge in and make them cough up some money.
• I didn’t look at the donor as a partner in mission. I looked at him as a source of cash. Even worse, I saw him as someone who owed the organization a donation, because he was on the board, hadn’t given in a while, and was supposedly loaded. Gosh, how arrogant could I have been?

I think about the story a lot. It’s still a painful one to revisit, but it changed the way I approach major gift fundraising. That day, I also learned a lot about grace, forgiveness, and second chances. I made a mistake, but my boss knew I could grow from it.

I’m grateful every day.


Jeff