The Earl of Chesterfield, the 18th-century British statesman and patron of the arts, had a number of concerns about his illegitimate son Philip, but one he revisited often in his posthumously published letters to the boy is about Philip’s correspondence. This species of worry ranged from handwriting (“shamefully bad and illiberal; it is neither the hand of a man of business, nor of a gentleman, but of a truant school boy”) to the boy’s prose style (“one principal topic of our conversation will be, not only the purity but the elegance of the English language; in both which you are very deficient”).

The latter became a particular concern after Chesterfield went to the trouble of setting the boy up in the world. In December 1751, he offered Philip some delightfully modern-sounding advice on his business correspondence:

The first thing necessary in writing letters of business, is extreme clearness and perspicuity; every paragraph should be so clear and unambiguous, that the dullest fellow in the world may not be able to mistake it, nor obliged to read it twice in order to understand it. This necessary clearness implies a correctness, without excluding an elegance of style. Tropes, figures, antitheses, epigrams, etc., would be as misplaced and as impertinent in letters of business, as they are sometimes (if judiciously used) proper and pleasing in familiar letters, upon common and trite subjects. In business, an elegant simplicity, the result of care, not of labor, is required.

In case Philip might mistake his meaning, and perhaps reasoning that a demonstration of his recommended prose style was worth much more than a mere description of it, His Lordship added, “Let your first attention be to clearness, and read every paragraph after you have written it, in the critical view of discovering whether it is possible that any one man can mistake the true sense of it: and correct it accordingly.”

Lord Chesterfield (Wikimeda Commons)

Lord Chesterfield’s advice on business writing, published in 1781, joined a heap of careful and voluminous 17th- and 18th-century attention to business correspondence. Titles such as The Young Secretary’s Guide, Or A Speedy Help To Learning; The Complete Art of Writing Letters; and Every Man His Own Letter-Writer were immensely popular bestsellers; The Young Secretary’s Guide went through more than 20 printings and piratings, from 1703 well into the 1750s. And if imitation is the highest form of flattery, we can gauge something of the book’s status in the fact that in 1730, someone got the bright idea to call his version The Young Secretary’s Guide Compleated: Being the Speediest Help to Learning. (This time, with 57 percent more learning.)

The format of the manuals, which were large collections of letters between imaginary but archetypal characters, also lent itself to recycling. An introductory letter to the reader would always lay out the general principles of entering into correspondence and the purpose of the manual: As the century went on and these manuals acquired ever increasing numbers of imitators, some of them would use this opportunity to explain, eloquently, the necessity of another entrant into the lists. Although we must allow for a certain natural exaggeration in what essentially amounted to a sales pitch or the 18th-century version of jacket copy, it’s from these introductory notes that we get a sense of the great regard in which business correspondence, and letter-writing generally, was held. From Every Man His Own Letter-Writer, for instance, we learn that “the importance and necessity of letter-writing, as it relates to our social and commercial concerns in every rank and station in life, are so evidently apparent, as to stand universally confessed…it becomes the duty and interest of each individual member of the community, to acquire a competent knowledge in an art which equally redounds to their credit and advantage.”

After this self-justification would follow a table of contents of each kind of letter contained within the book: a clear necessity, as the manuals represent just about every possible situation one can imagine occurring under the conditions of early British capitalism. Sample letter titles: “From a Shopkeeper in the Country to a Tradesman in London, Complaining of the Badness of his Goods” and “From one Friend to Another, generously offering him Assistance, on his having sustained great Losses by the Failure of a Correspondent” and the perennially popular “From a Guardian to His Ward, against a volatile, frothy French lover.”

A 1721 edition of the Secretary's Guide (Google Books)

As the genre—like Chesterfield’s letters to his prodigal son—was ostensibly directed at the young and naïve, almost every example of it follows a natural progression, from children writing to their parents thanking them for placing them in apprenticeships, or (in the case of daughters) in service, to masters writing up apprenticeship contacts once they had completed their own apprenticeships and acquitted themselves with enough linguistic propriety to advance in the world of business. Some later manuals tend to follow the same characters, from errant apprentices writing to their fathers for more pocket money, to young men writing to prospective father-in-laws to ask for their dowries and daughters, to older men writing to excuse their debts or requesting that debts to them be paid. The ubiquity of letters about every possible permutation of debt is especially prone to the creation of characters, whom you can follow through initial requests to successful (or unsuccessful) petitions to their creditors, and their creditors’ replies.

The popularity of this character-based approach, as well as its ecumenical view to the definition of “business,” possibly inspired the early English novelists like Samuel Richardson, whose first novel Pamela, Or Virtue Rewarded, concerned a young maidservant’s correspondence with her parents as she tries to fend off the dishonorable advances of her employer. Many of Pamela’s letters reproduce closely such frequent exemplars of the letter-writing manual as “A Letter of Thanks from a Daughter to her parents” and “A Daughter’s petition to her Mother that She Might Marry.” Although the novel later became the high bourgeois genre of leisure time, it was for a time the natural extension of learning how to write polite letters, a pursuit for which the wealthy had no real need of instruction.

Chesterfield’s obsession with a clarity so crystal that it could be understood by the “dullest fellow in the world” had a lot to do with the fact that to a greater extent than ever before, a letter-writer addressing a correspondent might not know much about his potential reader. Not only was the Industrial Revolution producing more commerce and more businessmen than ever before (not to mention the servants that they required to press their snappy business suits and feed them), but a possibly self-reinforcing combination of rising literacy and reformations of the mail service was also producing more correspondents, generally speaking. In 1680 a merchant named William Dockraw found that the expense of a postal service that charged by the sheet and the distance traveled—an expense that was furthermore charged to the recipient not the sender—inhibited commerce. He invented the Penny Post, which made sending letters in the greater London area a reasonable business expense. Although the service, which conveyed any letter or parcel under a pound within London for the aforementioned penny, ultimately ran afoul of the Duke of York in his capacity as collector of postal revenues, the 18th century continued to usher in both improvements to the cost and quality of postal service. Think email in the 1990s, or social media nowish, and you would come close to imagining the revolution in business communication that occurred in Philip’s youth. Letters, which had up to this point been an intimate communion of rich, artistic, and connected people well known to each other, underwent a dramatic democratization.

The subtitles of the business correspondence manual reveal this new instability in the idea of an audience. The Young Secretary’s Guide to Polite Epistolary Correspondence (1778) announces on its title page that it is appropriate for “persons in low or middling states of life”; The Complete Art of Writing Letters (1779) claims that it is “adapted to all Classes and Conditions of Life.” An introductory epistle in the form of a poem to the sixth edition to the original Young Secretary’s Guide commends the book for teaching the “plain Countryman” his “sense to recite.” Even Adam Smith, teaching rhetoric and belles lettres to young lawyers up in Scotland, weighed in: he praised Jonathan Swift, the early 18th-century satirist, for a style that one “half-asleep” could comprehend. Smith and others liked him embraced the idea that one should write as if one had the sloppiest, least energetic audience imaginable, figuring the rhetoric they recommended to their students in accordance with their beliefs about the low abilities and imperfect education of potential readers. “In letters concerning trade,” said Every Man His Own Letter-Writer, “the subject matter must be constantly kept in view, and the greatest perspicuity and brevity observed.”

Some letter writers (Wikimedia Commons)

The comprehensiveness of the manuals—some run to over 500 sample letters—is in fact a response to the lack of the formal education of their potential readers. These working-class readers (male and female) were perhaps literate enough to read but not literate enough to craft wholly original letters for their situations. So every potential situation received its own easily-adaptable template.

But there was another reason, too, and one that bears peculiarly on the kind of instruction in business correspondence that we give (or fail to give) students entering the world of work now. The teaching of rhetoric in the 18th century changed along with the conditions of commerce; formal rhetoric, which had previously been confined to an analysis of tropes according to the ancient ways of ethos, pathos, and logos, and the classification of kinds of arguments. Understandably, this was a bit abstract for the ordinary letter-writer attempting to persuade her parents to give her more pocket money. People like Adam Smith and his friend Hugh Blair were busy redefining rhetoric along lines recognizable to the manual writers who defended the importance of letters as “a common benefit to Mankind” and to both the “credit and advantage” of the writer. The beautiful was the practical, and the beautiful, at least when it came to business, was the brief.

Part of this program of practical rhetoric, as is clear from both the manuals and documents like Blair’s Lectures on Rhetoric and Belles Lettres, is extensive reading. Chesterfield, for instance, often incorporates something of the letter-writing manual in his letters to Philip by enclosing his own invented letters and asking his son how he would feel, were he the recipient of the letter. Would he be confused by the pronouns, for instance, a particular bugaboo with His Lordship, who recommended that they needed to be absolutely clear, even at the cost of awkward repetitions. Chesterfield also suggests Philip undertake a concentrated, lifelong education at the feet of “Dryden, Atterbury, and Swift” to CORRECT THAT CURIOUS INFELICITY OF DICTION” [emphasis not mine] which Philip acquired from his formal education. Good reading is good writing for Chesterfield, and in this, he shares an implicit assumption with the letter manual, the auto-didact’s friend.

* * *

Although I have often read correspondence manuals in my capacity as a literary scholar with an interest in the intellectual and economic history of early modern Britain, I have recently come to consider them in a different and more practical light, when dispatches from that shadow world outside ivory tower cross my desk. Often, these have to do with how badly academics like me train Millennials for the world of business, especially business writing. Most recently, a friend reported that a recent hire at his office responded to an email to say that it was too long and she didn’t read it. Even as we learn that young people do more writing these days than ever, we bemoan their lack of basic communication skills, the influence of texting on their orthography, and the fact that they talk like Internet cats to their potential employers.

The banal familiarity of the handwringing about the younger generation’s foibles doesn’t quite dull the shock of getting an email addressed “heyyyyy profesor” or punctuated with “dude” in lieu of commas or periods (I am not a dude). But there are other, subtler ways in which the world of the 18th-century correspondence manual resonates with our current context, ones that suggest that a revival of the letter-writing manual might be in order.

It’s possible to find plenty of guides to writing good business prose today, and many of them also tell readers to prize clarity and brevity, probably because the potentially far reach of any form of electronic communication makes us increasingly unsure of our readers. But it’s ultimately more than the occasional strangeness of 18th-century conditions of courtship or business (or, as was often the case, both) that constitutes the correspondence manual as fundamentally different from its 21st-century descendants. The biggest difference is that the 21st-century version of the letter-writing manual is mostly an abstract discussion of principles. But by reading both sides of the correspondence, and developing relationships with the ‘characters’ contained within, one truly develops a sense of what it is like to be the recipient of letters, not just the sender.

Stephen Pinker’s new writing guide, The Sense of Style, argues persuasively that the greatest mistake we make as writers is not understanding what it’s like to be our reader. What Pinker is dangling is essentially a very 18th-century concept, one articulated at great length by Smith in The Theory of Moral Sentiments: sympathy, or the ability to see ourselves as others see us. This other is an increasingly unknown quantity, coming from physical and intellectual places that are harder to conceive. The fictional characters who grew out of these letter-writing manuals are more and more understood as a vector for tutoring both empathy and sympathy, which suggests that when we teach students how to imagine and write to professional others, we could do a lot worse than throwing a big book of examples at them and getting them to think like readers, as well as writers.