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What does this expression really mean and where did it come from?

I'm assuming that it means you are just hanging upside down.

Maybe it means that your head is always hanging low and you are sad, but when you change your attitude, you're now looking up to the sky; holding your head high.

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    It means total disorientation. You don't know which way is up. – Hot Licks May 13 '15 at 17:43
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    (Note that this may be good or bad. A new romance may "turn your world upside down", or losing a job or coming down with some dire illness may do it. The common factor is that everything is different and you can't rely on your old habits to carry you through without really thinking about it.) – Hot Licks May 13 '15 at 17:53
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According to The Phrase Finder the expression 'upside down' is one of the oldest of the English language ( first part of the 14th century). It's meaning refers to :

  • things being inverted or in disorder - 'topsy-turvy', 'head over heels' (even though that is the usual arrangement), 'arse over tea-kettle' etc.
  • The mediaeval English also had the terms 'overset', 'overtumble' and 'topset downe', which have now gone out of use. Even the apparently unrelated word 'preposterous' was used in the Middle Ages with its literal Latin-based meaning of 'in the wrong order; inverted' (pre post, geddit?).
  • This profusion of similar phrases suggests a widespread interest in the recounting of stories of people falling over - matched today by the popularity of home video television shows - tet-beche.

The expression is common also in other languages:

  • The interest is common in other languages too; the Italians have the word sottosopra, meaning upside down, upset, commotion (literally 'under over'); the French even have a specialist term for a sequence of stamps, some of which are printed upside down - tête-bêche.

It's original form evolved to become the current intuitive one:

  • 'Upside down' was originally 'up so down', that is, 'up as if down'. The 'so' part migrated into various forms, 'upsa', 'upse' (which spawned 'upset') etc., in the same way as in phrases like 'ups-a-daisy' and 'upset the applecart'. The change from 'up so down' to forms like 'upset-down' and eventually 'upside-down' appear to be for no better reason than to make the expression's meaning more intuitive.

One of the oldest English expressions:

  • 'Upside down' doesn't sound especially old but, in its early forms, it can claim to be one of the oldest expressions in English. It joins the handful of phrases that can be dated from the first part of the 14th century or before, for example, 'haven't slept a wink', 'in the twinkling of an eye', 'by dint of'. The earliest version of 'upside down' known in print is in The proces of the seuyn [seven] sages. The precise publication date of that text isn't known, but it is accepted as being before 1340:

    • "The cradel and the child thai found Up so doun upon the ground."
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I've also heard it used to describe someone who was very ambitious making big changes to the status quo, as in "Bob just thinks he can come in to this company and turn the world upside down!" For people who are happy with the status quo, this is considered obnoxious and unnecessary. But some people, who are not so pleased with business as usual, think it a good thing.

Making a commotion and causing disorientation are both possible effects of having the world turned upside down by a person or group's radical actions.

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It's hard to be sure without context, but I think it means putting the world in disorder (through immoral activities)

From oxford (sense 1.1)

Upside down: In or into total disorder or confusion

burglars have turned our house upside down

The expression could have originated from the Bible:

And when they could not find them, they dragged Jason and some of the brothers before the city authorities, shouting, “These men who have turned the world upside down have come here also, [Acts, 17:6]

Young's Literal Translation

and not having found them, they drew Jason and certain brethren unto the city rulers, calling aloud -- 'These, having put the world in commotion, are also here present,

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I believe that in addition to being a popular turn-of-phrase, “turn the world upside down,” is a deep and enduring cultural meme that is demonstrably traceable back to ritual agrarian festivals---which were, themselves, a transformation of ancient hunter-gatherer rituals of ecstasy and catharsis---such as Saturnalia, Carnival, Samhain, Mardi Gras, Feast of Fools, the Season of Misrule, etc., which enacted a temporary reversal or dislocation of the social and sexual status quo.

The Season of Misrule is a descendent of Saturnalia, the Roman festival of the winter solstice. Somehow coming back around to the sunny side of our orbit suggested the inversion of social structures to the Ancient Ones. Turn the hourglass over, reach the limit and do an about-face; I suppose that’s more or less the logic, if logic has any role in this season of Unreason. see, Anna Castle

Twelfth Night (Wikipedia) a festival, in some branches of Christianity marking the coming of the Epiphany. Different traditions mark the date of Twelfth Night on either 5th January or 6th January; the Church of England, Mother Church of the Anglican Communion, celebrates Twelfth Night on the 5th and "refers to the night before Epiphany, the day when the nativity story tells us that the three wise men visited the infant Jesus."

In medieval and Tudor England, the Twelfth Night marked the end of a winter festival that started on All Hallows Eve — now more commonly known as Halloween. The Lord of Misrule symbolizes the world turning upside down. On this day the King and all those who were high would become the peasants and vice versa. At the beginning of the Twelfth Night festival, a cake that contained a bean was eaten. The person who found the bean would rule the feast. Midnight signaled the end of his rule and the world would return to normal. The common theme was that the normal order of things was reversed. This Lord of Misrule tradition dates back to pre-Christian European festivals such as the Celtic festival of Samhain and the Ancient Roman festival of Saturnalia. see, Wikipedia

Saturnalia was an ancient Roman festival in honor of the deity Saturn, held on 17 December of the Julian calendar and later expanded with festivities through to 23 December. The holiday was celebrated with a sacrifice at the Temple of Saturn, in the Roman Forum, and a public banquet, followed by private gift-giving, continual partying, and a carnival atmosphere that overturned Roman social norms: gambling was permitted, and masters provided table service for their slaves. The poet Catullus called it "the best of days."

In Roman mythology, Saturn was an agricultural deity who was said to have reigned over the world in the Golden Age, when humans enjoyed the spontaneous bounty of the earth without labor in a state of innocence. The revelries of Saturnalia were supposed to reflect the conditions of the lost mythical age, not all of them desirable. The Greek equivalent was the Kronia.

The popularity of Saturnalia continued into the third and fourth centuries AD, and as the Roman Empire came under Christian rule, some of its customs have influenced the seasonal celebrations surrounding Christmas and the New Year. see, Wikipedia [emphasis added].

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