In the fall of 1995, Joanna Rakoff dropped out of graduate school and returned to her parents’ home in the suburbs. “I want to write my own poetry,” she told her college boyfriend, “not analyze other people’s poetry.” Three months later, having done little more than allow her mother to buy her a wool gabardine suit and put her name in with a placement agency, Rakoff landed a plum job as an assistant to the president of a storied literary agency whose clients had included F. Scott Fitzgerald, Langston Hughes, and Agatha Christie.

Though Rakoff never names it in her memoir, My Salinger Year, the literary agency where she worked was Harold Ober Associates, and her boss – again not named – was Phyllis Westberg, whose most famous client was J.D. Salinger, author of the classic young-adult novel The Catcher in the Rye. When Rakoff arrives at Harold Ober in January 1996, the agency does not own a single computer. Agents still track submissions on little pink file cards and Rakoff spends much of her day behind an IBM Selectric typing correspondence recorded for her by Westberg on a 1960s-era Dictaphone machine.

Rakoff’s work is largely secretarial, but it pays $18,500 a year plus benefits and affords Rakoff, now a successful journalist and writer in her 40s, a valuable apprenticeship in the tight-knit world of New York publishing. For readers like myself, who are old enough to have begun their careers in the analog era, Rakoff’s tale carries with it a strong whiff of nostalgia. Like Rakoff, I was a humanities major with great artistic ambitions and little notion how to make good on them, and like Rakoff, I fell backward into a low-paying entry-level job in the culture industry. In my case, despite not having written a news story since high school, I wound up as a reporter at a local newspaper, an experience that gave me on-the-job training I am still using more than 20 years later.

But if you are now 23, the age Rakoff was when she started at Harold Ober, you may have been hung up by this fact: They paid her $18,500 a year, plus benefits. Granted, that’s hardly a lavish salary, just $28,000 in today’s dollars, but it beats interning for no pay, which is how most anyone in Rakoff’s position — college-educated and bright, but without relevant experience or contacts — can expect to start out in publishing today. I would go so far as to suggest that this helps explain the sleeper success of My Salinger Year, which has already gone into its third printing and been sold to the movies.

Every year, droves of smart young people from America’s best universities come to live in Brooklyn and work in New York publishing, just as Rakoff did 18 years ago, drawn at least in part by an image of working in hushed, book-lined offices where art and commerce meet and famous authors regularly drop by for martini-soaked lunches. What they find is an industry beset by tectonic shifts in technology and consumer leisure habits, in a knife fight against a certain Seattle-based e-tailer that now controls a third of its business. Against this backdrop, Rakoff’s tale of Dictaphones and gabardine suits, in which a literary agent could say in all seriousness, “I don’t know what an electronic book is, but I’m not giving away the rights to it,” can sound like a fairy tale set in a mythical land.

Of course, part of the joke of My Salinger Year is that the literary world Rakoff enters exists nowhere but at Harold Ober Associates. By 1996, the tech boom was underway and a generation of younger people, including Rakoff, had grown up using computers, but Harold Ober is still a world of paper in which even form letters must be individually typed by hand and the office photocopier is considered newfangled. “Until just a few years prior,” Rakoff writes, “assistants had typed every letter in duplicate, inserting into their typewriters a paper sandwich consisting of a thick sheet of creamy letterhead, a slender black wisp of carbon, and a piece of soft, pulpy yellow paper on which the carbon imprinted a copy of the note.”

The quaintness of the agency’s office fixtures — the dark-wood paneling and dim lighting, the heavy black desk phones and the “statuesque” receptionist answering them — is matched by its old-school business culture. Westberg, who swans into work at 10 “swathed in a whiskey mink, her eyes covered with enormous dark glasses, her head with a silk scarf in an equestrian pattern,” doesn’t believe in multiple submissions and abhors publisher bidding wars, which she considers “uncouth.” “We send things out to one editor at a time,” she tells Rakoff. “We match writers with editors. We have morals.”

Morals Westberg may have, but her stodginess is costing her clients — except of course for J.D. “Jerry” Salinger, whose hit books from the 1950s and ’60s, including Nine Stories and Franny and Zooey, are still keeping the lights on. Save for a single brief appearance, Salinger remains an off-stage presence, a distant voice on the phone calling from his compound in Cornish, N.H. Disgusted by modern publishing and overwhelmed by the tidal wave of appreciation his work provokes in his most ardent fans, Salinger has walled himself off from the world, declining to publish the novels he claims to be still writing and refusing to even look at the stacks of letters from readers hungry to share their problems with the creator of Holden Caulfield, American literature’s great cynical romantic.

This leaves Rakoff, as the assistant to Salinger’s agent, the unenviable task of sending letters informing his readers that their literary hero doesn’t want to hear their praise or their problems — a job at which Rakoff fails magnificently. Refusing to simply retype the form letter, whose original dates back to 1963, Rakoff begins composing letters of her own, dispensing consolation and advice as she sees fit. Some write to thank her, while others fume at her presumption, but as a gesture, her espistolary mischief makes sense. Though the pages of My Salinger Year are lousy with writers, at heart this is a book about readers, professional and unprofessional, who hunger for communion with the remote and often troubled authors they revere.

For all her limitations as a literary agent — and they are legion, if Rakoff’s account is to be believed — Westberg is a dedicated professional reader who sees her role in life as fostering an atmosphere in which literary talent can thrive. “For my boss, the Agency was not just a business,” Rakoff writes. “It was a way of life, a culture, a community, a home. It was more in common with an Ivy League secret society or — though it would take me time to see the extent of this — a religion, with its practices defined and its gods to worship, Salinger first and foremost.”

What Rakoff doesn’t say, because anyone who would read an insider’s memoir of the book business already knows it, is that it is precisely these professional readers who have been hurt most by the collapse of the old model of publishing. In the short term at least, the digital age has been a gift to nonprofessional readers. Books, which before chain stores were often expensive and hard to find, are now cheap and available at the push of a button. Readers also have more access to writers than they ever have, to the point that it’s hard to see how a shy, reclusive writer like Salinger or Thomas Pynchon could build a readership in an era of Facebook friending and constant book tours and signings.

Writers, of course, bemoan the withering of the publishing industry, and to a degree they are right to do so. Tight profit margins for publishing houses mean fewer book contracts and smaller advances. But do writers really have it so bad? Without a doubt, there is a gaping hole in the market for writers whose work falls between the plot-driven, Zeitgeisty fiction major publishers still pay big money for and the more literary, craft-driven fiction that ends up at indie houses. These so-called midlist authors, whose toil pays off not in a blaze of bestseller glory, but over the long haul in slow but steady sales, are now being shunted into self-publishing — or more often, are finding themselves recalibrating their work toward the more viable poles of the literary/commercial divide.

Still, thanks to self-publishing and the rise of MFA programs as a subsidy system for poets and literary novelists, writers today have more paths to publication and more ways to make money as writers than has ever been the case. A less-heralded casualty of the digital age is the disintegration of the lower rungs of the ladder that have long led young, smart readers into the caste of professional tastemakers.

Think for a minute of 23-year-old Joanna Rakoff at her humming Selectric typing those form letters to Salinger’s fans. Today, fans communicate directly with authors or with each other online, and if one does route a message through a publishing house or literary agency it is typically deleted unread or farmed out to an unpaid intern. The same goes for Rakoff taking her boss’s correspondence from a Dictaphone. Today, agents and editors handle their own email and use their assistants to screen out people they don’t want to deal with. That’s a real job, as anyone who reports on the publishing industry can tell you, but it’s a lot less work than typing thousands of letters.

Publishing is hardly alone in seeing its lower ranks eviscerated by time-saving digital devices, but in the book business the problem is particularly acute and widespread, affecting not just agents and editors, but critics and booksellers. The top positions in each field still exist and can be well-paid, but the gateway jobs where generations of young people learned the trade, are being devalued or outsourced. In publishing, it’s the near-mandatory unpaid internships that make it so hard for anyone without rich parents to enter the business. In criticism, it’s the blogosphere and reader sites like Goodreads that outmoded the books page in all but a few newspapers and magazines. In bookstores, it’s Amazon that has digitized the recommendation role that well-read independent booksellers play in the lives of their customers. You can still be a passionate reader, but it’s getting harder to make a profession of it.

At the end of My Salinger Year, Rakoff leaves Harold Ober to be a writer, but not before she experiences the thrill of being a professional reader when she helps Westberg sell a story for one of her clients. “Rationally, I know that it’s just a business transaction,” she tells her college boyfriend. “But I can’t help feeling that there is more to it: I brought this story into the world. People will read it because I placed it. Until I placed it, the story belonged only to the writer. Now it will belong to the world.”

In a final twist that will not surprise many, Rakoff reveals that around the same time she left the literary agency, she ditched the nogoodnik writer boyfriend she was living with in Brooklyn, and now many years later, after a failed marriage, she has reunited with the college boyfriend to whom she poured out these first thoughts of readerly pride. Frankly, I found Rakoff’s account of her affairs outside the office less compelling — and less believable — than those of her days in the hopelessly outdated offices of Harold Ober. I was also put off by the book’s coyness in declining to name its central characters, especially since she has identified the major players in earlier versions of the story that can be found with a few keystrokes on Google.

But it is hard not to be charmed by her sepia-toned portrait of a time when a smart young woman in possession of no more than a decent wool suit and rudimentary typing skills could be acculturated into the profession of reading. Maybe it’s just as well that those jobs are going away. It was a sexist system, and a deeply conservative one. Young would-be publishing professionals may find it hard to get paid to learn their trade, but they’re not spending their days fetching coffee and doing things the old way just because that’s the way people have always done them. But it’s a loss, too — one Rakoff captures with elegance and humor in My Salinger Year.