Over the years, I’ve herded my share of cats in building businesses and creating art. I can remember the first time I saw this video and how many people I sent it to. The EDS Herding Cats commercial was first aired on TV during the Superbowl XXXIV (the only reason I watch the Superbowl is for the ads) in 2000.
Search on the Web lists a couple interesting definitions:
“An idiomatic saying that refers to an attempt to control or organize a class of entities which are uncontrollable or chaotic. Implies a task that is extremely difficult or impossible to do, primarily due to chaotic factors.” (wikipedia)
“If you have to try to co-ordinate a very difficult situation, where people want to do very different things, you are herding cats” (usingenglish.com)