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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?
Cats: Ya!
herding cats by catherdmaster January 3, 2009
Related Words

Fart Herding

The act of using flatulence to direct a particular person or group to a certain location. Often used (with little success) in a bar environment by someone who just had a Mexican dinner.
Friend #1: "Where did Billy go, he keeps disappearing"
Friend #2: "Oh he's over there fart herding that group of brunettes so they some closer"

Cabbage Heading 

The act of a female placing her genitalia on the forehead or face of another person in order to create sexual humiliation and to assert dominance over another. The female equivalent of teabagging.
Chun Li is cabbage heading T. Hawk after she whupped his ass in a street fight.
Cabbage Heading by Luis Reyna January 17, 2009

Herding cats 

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.
Herding cats by eMeS December 22, 2005

Bang Heading 

When someone tries to "Head Bang" to a song but do it in such an off beat or weird manner that it's just sad.
Guy 1: "Dude, check out this new song I found."
Guy 2: "Oh wow, it's cool. *wtf? I don't even know*"
Guy 1: "Alright, cut out the Bang Heading, you're embarrissing me. . ."
Bang Heading by Tortuga Dorian November 25, 2010

Turtle Heading 

When shit starts playing Peek-a-Boo with your butthole.
Bro we really need to find a shitter! I've been Turtle Heading for the last 20 minutes! If I don't get there soon Mr. Hankey is gonna come visit.
Turtle Heading by RoyalTokes July 7, 2018