The plot focuses on The Fool card of the tarot, who is portrayed as a silhouette of a young man wearing a peaked, feathered cap, curled-toed shoes, and carrying a knapsack on a stick.

The Fool journeys through four kingdoms (each representing a suit from the minor arcana of the tarot), where he encounters other characters, who either give him more information or provide him with additional tasks.

Once the map is successfully completed, other designs on the map become active click targets and can be used as clues or processes to decipher the true final puzzle: The Book Of Thoth, hidden within the chapter The High Priestess, which requires the reader to peruse the entire story as continuous prose and identify a number of phrases hidden within the narrative.

Cliff Johnson, who at that point had worked as a filmmaker, was inspired by films like Sleuth and The Last of Sheila which included puzzle-mysteries for the viewer to solve; he aimed to host "mystery" dinner parties where players would uncover clues to find the hidden secrets.

The concept, a series of puzzles and a narrative that fit together into an overarching mystery like a jigsaw, was an early incarnation of what became The Fool's Errand.

[3] His goal was to “make the experience pleasant and solvable in a single afternoon.”[4] His initial approach to programming was guided by his experience making animated film, which involved "a very tedious frame-by-frame process", creating a blueprint and putting the pieces together to assemble the whole picture in a manner similar to a jigsaw puzzle.

[citation needed] The Fool's Errand did not sell well at first, but after a very positive July 1988 review in MacUser it became very successful, causing Miles Computing to port the game to other platforms.

[10] Macworld reviewed the game positively, calling it a difficult and epic collection of diverse puzzles that demanded "considerable interaction and ingenuity."

[14] STart's reviewer confessed that he had come close to finishing The Fool's Errand but that "I felt like I'd run, and lost, a mental marathon".

[15] The Games Machine awarded the PC version of The Fool's Errand its Golden Scroll and rated it 93%, calling it "fresh, original and addictive".

[18] Amiga Format rated the game 70%, praising the "sheer number and variety of the puzzles" and calling it "an intelligent use of the machine" despite reservations about the graphics and sound quality.

[22] GamesTM featured The Fool's Errand in its "Greatest Retro Game Ever" column, calling it "obscenely addictive" and "revered by nearly everyone" who played it.

They wrote, "One of the best puzzle games ever produced — everything from mazes to cryptograms worked into an elaborate, witty narrative, and presented with exceptional graphic flair.