nailing jelly to a tree
idiom. Tackling a particularly messy, and probably impossible, problem.

Example Citations:
How do you measure happiness, anyway? Happiness, like pain, has a threshold that varies from person to person. Defining it is about as easy as nailing jelly to a tree.
—Lyndall Crisp, "Consumed By Unhappiness," Australian Financial Review, June 30, 2001

He presents his data not merely to confirm the occasional altruism of these organizations but as partial confirmation of the hypothesis of the great theoretical sociologist Max Weber, who observed in the evolution of Western society a process of rationalization manifested in, among other ways, the direction of law reform. . . . Weber's hypothesis might thus be viewed as a more rigorous kin to Thomas Carlyle's dictum that the arc of history is long but points toward justice. An effort to quantify such a cosmic trend has some of the aspects of "nailing jelly to a tree."
—Paul Carrington, "Beyond Monopoly," Science, May 20, 1988

Earliest Citation:
—Jerry Willis, Nailing Jelly to a Tree, Dilithium Press, April 1, 1981

The originator of this phrase may have been psychologist Jerry Willis, who published a book called Nailing Jelly to a Tree in 1981. This book's title is mentioned in several articles after that (including William Safire's "On Language" column in The New York Times). The second example citation is the first media citation I could find that uses the phrase without reference to the book.

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