A friend of mine recently organized an annual charity event (this is what people do with their limited free time Washington, DC). This year’s event was the fourth, and it had all the signs of growing pains. It had grown beyond grassroots, but was far from an institution. In an effort to elevate the prestige and funds raised by the event, my friend brought in additional partner organizations and volunteers, built a new organizational structure, and increased press coverage among other things. The entire team of organizers, including my friend, was volunteers, all with different expectations for the event, from how much time they should reasonably have to commit a week to how event information should be positioned on fliers. Managing volunteers’ different expectations became the largest challenge in bringing the event together.

“Everyone that I spoke to that attended the event loved it. They said it was the best ever,” my friend debriefed, “I wish all of the volunteers felt the way the attendees did.”

“It’s good experience for your career,” I advised. “If you ever want to rise to a position of power, keeping everyone happy and doing what they’re supposed to while accepting that at no given point everyone will be happy or doing what they’re supposed to is good practice. And you might as well get used to not being liked.”

“I’m okay with not being liked. What I cared about was the event being a success.”

“Do you think it was a success?”


“No? Why? You got all that good feedback from attendees and partners.”

“Yes, but it didn’t meet my expectations.”