A metaphor that means don't be mainstream, think freely and creatively. Don't just see the obvious, pay more attention to the content. Don't discount anything as unrelated or unconnected. Make an effort to push your thinking up to and beyond its limit. All the talents that you've developed at school should come in handy when you need to beef up your out of the box thinking skills.
Step back and see if the solution to the problems lie outside the box. One must think outside the box.
by John Ortberg February 8, 2018
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"Think outside the box" is the phrase every douchebag boss you've ever had has said to you at least one time. "Think Outside the Box" as a phrase itself has no meaning. It literally has no useful meaning whatsoever.

What they WANT it to mean when they say it (They being of course your superiors at every job you hated when you were younger) is for you to exercise your mind and figure out the solution to a problem.

The real meaning? "I have no idea how to answer your question, so figure it out for yourself."
1.) You: Sir, I found the account you wanted me to research, but in what way am I supposed to approach a 60 year old man with no liquid assets living on social security?

Your superior who's actually awful at his AND your job: Think outside the box!

2.) You as a 3rd grader: Dad, what's 9/3?
Your dad: 2.

You as a 6th grader: Dad, if x-10 = 15, what is x?
Your dad: 25

You as a freshman in high school: Dad, if (x-10)+5(2) = 20, what is x?
Your dad: ...Think outside the box!
by Aurinax September 9, 2010
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The thoughts a male has during intercourse to delay his impending ejaculation. Examples include sports, work, movies and his grandmother's loose, grungy, mothball ridden cunt.
Mike 2: Dude I came in like .08 seconds last night, my wife was pissed.

Mike 1: Guess you weren't thinking outside the box!
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Try to solve the problem with unorthodox methods. Consider any idea, no matter how unusual.
Solving the difficult riddle required ideas that came from thinking outside of the box.
by Diggity Monkeez February 16, 2005
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Old - Phrase in office-speak suggesting the use of unorthodox approaches to solve otherwise difficult problems. Not a bad phrase, but too many pointy-haired-boss types latched on to it and used it as a knee-jerk response when asked for input, thus blanching it of all meaning.

New - Happy-hour phrase meaning "Get your mind off the poontang - we're talking sports now!"
Old - Cube Monkey: Boss, I'd like your input on this problem.
Boss: Think outside of the box, Monkey.
Cube Monkey: Well, I thought you may have some time-saving insight, since you're paid to be my professional superior and all...
Boss: Just think outside of the box, Monkey!
Cube Monkey: Right. Hey! I'll use the fuckyoubossoscope!
Boss: There you go, Monkey!

New - Guy 1: Think the Rams have a chance this year?
Guy 2: It'll be tough, but anybody can make the playoffs in the NFC... What do you think, Trey?
Guy 3: Did you see the ass on that marketing intern? Damn! I could write a poem about that ass!
Guy 1: Hey, Trey... we're over here... football conversation?
Guy 2: Yeah, Trey - Think outside of the box!
by The Evil Steve August 30, 2005
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An unoriginal phrase/cliche following a conventional way of thinking used to encourage original thought and unconventional thinking, asking you do challenge the paradigm in a phrase that doesn't challenge the paradigm. Saying "Think Outside of the Box" is "Thinking Inside of the Box". This is similar in this aspect to the phrase "avoid cliches like the plague", warning against using cliches through the use of a cliche.
Employee: (quietly) Okay, since you're obviously not...

Ellen: Yeah, that's good advice. Maybe you should take it.
by 1pro3u January 12, 2014
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