Any difficult activity of uncertain outcome involving numerous and often competing factions that is of dubious value.
The latest project that I'm manging at work involves so many different groups that it's just like herding cats.
The phrase herding cats comes from the common saying that something involving coordination of many different groups or people is as difficult as herding cats. One of the commonly encountered uses of the term in technical fields is the phrase "Managing programmers is like herding cats" or "Managing engineers is like herding cats". In education it would be "Managing students is like herding cats". In reality, it would be "Managing cats is like herding cats." It refers to the individualism common in the stereotypical examples of programmers and domesticated cats. A similar phrase, allegedly of Irish origins, is "Minding mice at a crossroads".
Me: Yo. I was having trouble.
You: So, managing cats was like herding cats?
Trying to get a group of silly girls/boys in one place to take a silly picture of them.
"I have gotten three other people to agree to do it, but actually getting them in front of the camera is like herding cats."