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Phrase origins can be interesting.  For example, “clog up the works” is a phrase that could’ve derived from the Luddite Dutch workers throwing their clogs in the machinery to wreck it.  Therefore, it would appear the phrase “clog up” is of Dutch origin.

A fool’s errand, or a pointless undertaking, could’ve originated in the Middle Ages.  The word “fool” is an insult these days.  However, that was not the case in the Middle Ages.  A fool was a naïve simpleton but was regarded with respect and even admiration-sort of like “The Fool On The Hill” by the Beatles.  It has long been part of the initiation of new recruits to send them on 'fool's errands'. A credulous beginner might be sent to the stores to fetch a skyhook or a tin of striped paint. The first references to 'fool's errand' come in texts from the 18th century. An early example is from the Yorkshire-born clergyman Edmund Hickeringill's Priest-craft, 1705: Did not the Pope send all the Princes in Christendom upon a Fool’s Errand, to gain the Holy Land, that he might (as he did in their absence) rob them of their territories.

Given that playing tricks on the simple-minded must have been happening since Adam was a lad, it seems odd that 'fool's errand' didn't emerge into the language until the 18th century. The reason for this is that medieval England had a different name for the sport, which was a 'sleeveless errand'. From the Tudor era to around the 1700s, 'sleeveless' was very commonly used to mean 'futile' or 'trifling'. 'Sleeveless answers' were those that gave no useful information and a 'sleeveless errand' was a fool's errand, often used to get someone out of the way. The historian Raphael Holinshed used the expression in Chronicles, 1577:

So, as all men might think that his prince made small account of him, to send him on such a sleeveless errand.

'Sleeveless' had also been used for centuries before with the same meaning as now, that is, 'without sleeves', so it's reasonable to assume that's where the 'futile' meaning of sleeveless derived. What's not clear, and despite my best efforts I've not been able to find out, is why 'sleeveless' was used with that meaning. Such usage of the word has long since died out and, although it's not difficult to make guesses at the link between 'sleeveless' and 'futile', to know the real truth of that derivation we may need get aboard a time machine.  This last one is appropriate for these times.  To keep a stiff upper lip means to remain resolute and unemotional in the face of adversity or even tragedy.  The phrase is similar to “bite the bullet” or “keep your chin up”.  It has become symbolic of British and particularly of the products of the English public-school system during the age of the British Empire.  In those schools the “play up and play the game” ethos was inculcated into the boys who went onto rule the Empire.  That “do your duty and show no emotion” attitude was expressed in Alfred Lloyd Tennyson’s The Charge of the Light Brigade: Theirs is not to reply.  Theirs is not to reason why.  Theirs but to do and die.  Into the Valley of Death rode the 600.

In more recent years the stiff upper lip has gone out of favor in the UK and British heroes have been able to show more emotion. Footballers now cry when they lose and soldiers cry at comrades' funerals, both of which would have been unthinkable before WWII.

So, where did the 'stiff upper lip' originate? In 1963, P. G. Wodehouse published a novel called Stiff Upper Lip, Jeeves, and you can't get much more English than that.

Strange then that a phrase so strongly associated with the UK should have originated in America. The first printed reference to it that I know of is in the Massachusetts Spy, June 1815: "I kept a stiff upper lip and bought a license to sell my goods."

That citation doesn't explicitly refer to keeping one's emotions in check, but a slightly later one, from the Ohio newspaper The Huron Reflector, 1830, makes the meaning unambiguous: I acknowledge I felt somehow queer about the bows; but I kept a stiff upper lip, and when my turn came, and the Commodore of the Police axed [sic] me how I come to be in such company... I felt a little better."

The expression can be found in several US references from the early 19th century and was commonplace there by 1844, which is the date of the earliest example that I can find from a British source.  (www.phrases.org )  

That’s the end of our little trip down the information superhighway for the week.