Geoffrey Chaucer and his side project: The Canterbury Tales

In 14th-century London, a middle-aged customs official hunches over ledgers in his cramped office above Aldgate—one of the historic gates in the defensive wall of medieval London—meticulously recording wool and wine duties for the Crown. By day, Geoffrey Chaucer (c.1343–1400) is the consummate royal bureaucrat. By night, this same man transforms, setting aside fiscal records to craft The Canterbury Tales, a vibrant collection of stories following pilgrims journeying to Canterbury. In an era ravaged by plague, war, and social upheaval, Chaucer performed a remarkable balancing act—royal servant by profession, literary iconoclast by passion—creating what would become the cornerstone of English literature.

From merchant's son to the king's trusted official, Chaucer climbed the ranks of medieval government during one of England's most turbulent centuries.

Born to London wine merchants, young Geoffrey secured a position as a page in a noble household, absorbing "refined courtly manners" and French literature. His early exposure to aristocracy launched an unlikely ascent through royal service. By his twenties, he had already fought in the Hundred Years' War, been captured by French forces, and ransomed by King Edward III—"a sign of his value to the English crown."

In 1374, Chaucer landed the position that would define his professional life: Comptroller of Customs for the Port of London. The job required him to "keep the records himself as well as oversee the collectors" of customs taxes on wool, leather, and wine exports. This was "exacting, detail-oriented work" that consumed his days with calculations and enforcement. His diligence earned him reappointment under King Richard II. Records show that in the 1380s, he sometimes "deputized his customs duties to others," perhaps carving out precious hours for writing between official obligations.

His daily work at the customs house brought him face-to-face with "Italian bankers, Flemish traders, English wool merchants, sailors from Spain"—a diversity of characters that would later populate his tales with startling authenticity. When his Merchant pilgrim discusses piracy between "Middleburgh and Orewell" or currency exchange schemes, we recognize the customs officer's intimate knowledge of trade routes and mercantile pretensions.

His civil service career expanded to include diplomatic missions across Europe, assignments as Justice of the Peace in Kent, a seat in Parliament, and oversight of royal building projects as "Clerk of the King's Works" from 1389. Through these roles, he developed "how to flatter, how to read between lines, and perhaps how to veil criticisms behind polite language"—diplomatic skills that would later allow him to craft social critique without offending powerful patrons. By 1385, he "moved out of London to Kent," possibly "seeking a quieter life away from the political storms" of court where he could balance royal service with his growing literary ambitions.

During whatever hours remained from his government duties, Chaucer nurtured literary ambitions that would transform English forever.

While serious writers of his time used Latin or French, Chaucer made the unorthodox choice to write in the "English of the streets and markets," a decision proving "the language of commoners could be artful, flexible, and profound." This cultural statement elevated native English from its lowly status to a vehicle for sophisticated literature.

His diplomatic travels exposed him to Italian literary giants "who were little known in England at the time." In Florence and Milan, he encountered works by Dante, Petrarch, and Boccaccio, whose Decameron provided a storytelling framework. Yet Chaucer boldly reimagined this concept—rather than nobles sharing tales in elegant seclusion, his pilgrims were a cross-section of society whose stories became "a kind of duel" as characters "used tales as weapons to get back at or even with the previous tale-teller."

Chaucer began The Canterbury Tales in the late 1380s with staggering ambition—envisioning 120 stories from his diverse pilgrims (though completing only 24). The range was unprecedented: chivalric romance followed immediately by bawdy humor, sacred devotion alongside cutting satire. This wasn't mere entertainment but a breakthrough literary project capturing English society in all its contradictions, created during stolen moments. We can imagine him "trudging home after a day balancing ledgers, perhaps stealing a few late-night hours to scribble verses by candlelight."

What Chaucer's contemporaries knew as a "competent official and courtier" history remembers as the visionary who gave voice to "knights and clerks, merchants and millers alike," creating "a new literary language and a panoramic portrait of his era."

The Canterbury Tales presents an unprecedented cross-section of medieval society reflecting the breadth of Chaucer's experience—from royal courts to bustling ports, from legal chambers to country inns. His keen observations, collected during decades of public service, animate characters with an authenticity that still resonates six centuries later.

Chaucer's dual life reminds us that transformative creativity can emerge from the margins of a busy professional existence. By "fulfilling his roles in government, he gained the knowledge, security, and broad perspective that fed his writing." In turn, his poetry "humanized the very world he administered."

When Chaucer died in 1400, he was buried in Westminster Abbey—"fittingly, in close proximity to the halls of power he served" in what would later become Poets' Corner. His final resting place symbolizes the dual identity he maintained throughout life: the loyal servant of the crown who became the father of English literature "almost furtively," writing by candlelight after his day's duties were complete. The bureaucrat's records have long since crumbled to dust, but the stories he crafted in spare moments continue to illuminate our understanding of humanity.