guess-work (n.)

c. 1300, gessen "to infer from observation, perceive, find out; form an opinion, judge, decide, discern; evaluate, estimate the number, importance, etc. of," perhaps from Scandinavian (compare Middle Danish gitse, getze "to guess," Old Norse geta "guess, get"), or from or influenced by Middle Dutch gessen, Middle Low German gissen "to guess," all from Proto-Germanic *getan "to get" (see get (v.)).

The prehistoric sense evolution then would be from "get," to "take aim at," to "to estimate." Meaning "to hit upon the right answer" is from 1540s. The spelling with gu- is late 16c., sometimes attributed to Caxton and his early experience as a printer in Bruges. Related: Guessed; guessing.

Guessing game attested from 1650s. To keep (someone) guessing "keep him in a state of suspense" is from 1896, American English.

[T]he legitimate, English sense of this word is to conjecture; but with us, and especially in New England, it is constantly used in common conversation instead of to believe, to suppose, to think, to imagine, to fancy. [Bartlett, "Dictionary of Americanisms," 1848]

Old English weorc, worc "something done, discrete act performed by someone, action (whether voluntary or required), proceeding, business; that which is made or manufactured, products of labor," also "physical labor, toil; skilled trade, craft, or occupation; opportunity of expending labor in some useful or remunerative way;" also "military fortification." This is from Proto-Germanic *werka- "work" (source also of Old Saxon, Old Frisian, Dutch werk, Old Norse verk, Middle Dutch warc, Old High German werah, German Werk, Gothic gawaurki), from PIE *werg-o-, a suffixed form of the root *werg- "to do."

The meaning "physical effort, exertion" is from c. 1200; that of "scholarly labor" or its productions is from c. 1200; the meaning "artistic labor" or its productions is from c. 1200. The sense of "labor as a measurable commodity" is from c. 1300. The meaning "embroidery, stitchery, needlepoint" is from late 14c.

Work of art attested by 1774 as "artistic creation," earlier (1728) "artifice, production of humans (as opposed to nature)." Work ethic recorded from 1959. To be out of work "unemployed" is from 1590s. To make clean work of is from c. 1300; to make short work of is from 1640s.

Proverbial expression many hands make light work is from c. 1300. To have (one's) work cut out for one is from 1610s; to have it prepared and prescribed, hence, to have all one can handle. Work in progress is from 1930 in a general sense, earlier as a specific term in accountancy and parliamentary procedure.

Work is less boring than amusing oneself. [Baudelaire, "Mon Coeur mis a nu," 1862]