The summer of 1988, David Samuels was between his junior and senior years at Harvard and decided he wanted to cover the Republican convention in New Orleans.

His journalism experience had been limited to writing parodies of news items for the Harvard Lampoon, and he had little in the way of access set up for the convention.

He stopped in to the offices of the Washington City Paper, where he met Jack Shafer, the editor, and told him he was convinced he could penetrate the event and gain access to the big players there because he owned a tuxedo.

Mr. Samuels remembers Mr. Shafer, better known today as Slate’s media critic, as “this dude with a leather jacket.”

Mr. Shafer remembers Mr. Samuels, too. “David was a bright and bold little fuck.”

Mr. Shafer made Mr. Samuels the kindest offer an editor can make to a fledgling journalist: “We have this thing called spec …”

The tuxedo worked. Mr. Samuels got into the convention and glad-handed George H. W. Bush, his son, George W. Bush, Henry Kissinger, and others. He filed his story—4,000 Hunter S. Thompson-inflected words—and got his spec: Ten thin cents a pop.

“I was like, ‘Huh, I can make 400 dollars at this!’” Mr. Samuels said.

Twenty years later, Mr. Samuels has had the sort of bylines today’s Harvard juniors would give anything for. He’s been nominated for two National Magazine Awards, received prestigious fellowship appointments and been invited to teach at N.Y.U.’s magazine journalism department. He’s also married to New York Times Magazine columnist Virginia Heffernan, with whom he has a 2-year-old son.

Last week, the New Press released two books he wrote: Only Love Can Break Your Heart, which collects some of Mr. Samuels’ articles from The New Yorker, Harper’s, The New York Times Magazine, among others, and The Runner, an expanded version of a New Yorker story about James Hogue, a highly accomplished runner and less accomplished grifter who scammed his way into Princeton in his late 20’s by claiming to be a self-educated, part Native American teenager named Alexi Indris-Santana.

Kirkus Reviews called The Runner “a dizzying, exhilarating tale of deception”; The New York Times praised Samuels as “an elite narrative journalist” in a Book Review essay.

But a recent visit to Mr. Samuels’ office found the writer despondent, even a little hopeless, and talking about retirement.

“Burnout is inevitable in this profession. It’s inevitable doing this sort of intense, long-form magazine writing,” Mr. Samuels was saying as he sat munching supermarket sushi at his desk in a small, wood-paneled studio he rents on the first floor of a creepy Victorian in Brooklyn Heights.

Aged 41, Mr. Samuels has the soft, rumpled appearance of someone who spends a lot of time alone in a room writing. In one of the essays in Only Love, Mr. Samuels looks at himself through his wife’s eyes and sees “her soft-bellied husband” and compares himself to the “neighborhood characters who tote tattered shopping bags filled with books and periodicals along the Promenade.”

The couple met at a party where Mr. Samuels spent the majority of the night flirting with Ms. Heffernan’s friend, who was “hot and funny and wearing a really nice dress.” But it was Ms. Heffernan who talked to him about his work, and after some insightful criticism and a couple of years of courtship, the two were married in 2003.

“I now have all the trappings of normalcy that I found completely impossible to maintain longer than a month,” Mr. Samuels said.

Between the lines of many of the pieces in Only Love is a loneliness borne of too many weeks spent in hotel rooms in Eugene, Ore., and other less glamorous locales, reporting his stories, for which he insists on face-to-face contact even for minor interviews, and in encounters with complete strangers, during which Mr. Samuels tried “to seem casual and relaxed while concentrating on them really intensely in a way that hopefully doesn’t creep them out.” Now, he says, “I’m very happy and I thank God every day that I have a wife who loves me.

“I have to earn every line I write by actually going somewhere, staying in some horrible hotel—although the hotels have gotten nicer. … I have to write and rewrite these sentences until there’s a world that’s self-contained.”

When he profiled Condoleezza Rice for The Atlantic in 2007, he pinballed from New York to Washington, D.C., from California to Ramallah and Jerusalem for a year, all to get a few precious encounters with the secretary of state. He used part of those interviews to ask Dr. Rice why Americans don’t play soccer in an attempt to get an unscripted answer out of her. (“I’m not going there!” she told him.)

He’s written about anti-World Trade Organization protesters in the Pacific Northwest, the organizers of Woodstock ’99, patients at the Hazelden Clinic, and the demolition of the Sands Hotel and Casino in Las Vegas.

And when he’s not on the road, he spends seven hours a day, six days a week in this office in Brooklyn.

Mr. Samuels’ profession, that of a magazine writer, is one that “at this point exists half in memory,” he said. “What I do is a throwback.”

What he does is go to places, meet people, gain their trust and tell their stories at length. What he does not do is attend fantasy baseball camp with the Rock (and an ever-present studio publicist) so as to spin a “revealing” (but not too revealing) 600-word profile to accompany a David LaChapelle photo shoot tied to the release of a big summer movie. This may explain why he’s never been asked to be on the staff of any magazine: He’s not the sort of writer who can produce polished, promotional writing under tight deadlines. He’s not a man of today’s magazine.

“I wouldn’t go so far as to say I’ve wanted to ‘sell out,’ because that’s not true, but at the same time, no one’s ever asked me. … In my entire career, no one’s offered me a contract of any kind. Details hasn’t wanted me, let alone Rolling Stone, Esquire, The New Yorker. I am literally unemployable.”

For someone unemployable, he’s not doing so badly for himself. He had a tough time selling Only Love Can Break Your Heart, which the New Press decided to pair with a stand-alone volume in order to drum up more reviews.

“Nobody wants to publish a collection of magazine pieces. It’s like saying, ‘Here’s a bag of used Kleenex: Would you like to hold it for a while?’… The publishing industry is convinced that this stuff is garbage. Increasingly, it is garbage. If you look at magazines today, how much is there that you’d want to read a year later, let alone 10 years later?”

Just above the toilet in the combined bathroom-kitchenette in Mr. Samuels’ studio, there’s an old black-and-white photo of a news vendor peering out of a newsstand. Surrounded by picture magazines and newspapers, he looks like a man in solitary confinement. It’s not hard to imagine why Mr. Samuels would be drawn to such an antique image. Like old copies of The New York Herald or Look, Mr. Samuels sees the world he inhabits fading before his eyes.

“Everybody talks in every decade about the golden age that preceded them, but in this case, you can measure it. You can measure it by the length of the stories,” he says. “The articles in The Atlantic are half the length that they used to be; the articles in The New Yorker are half the length that they used to be.”

Jack Shafer disagrees, citing several of the magazines Mr. Samuels writes for as well as recent, epic pieces by Rich Cohen in Vanity Fair (“Jerry Weintraub Presents!”) and Ben Wallace-Wells in Rolling Stone (“How America Lost the War on Drugs”) as proof that there are as many spaces as ever for long-form journalism. But there’s no denying that The New Yorker no longer runs “that sprawling New Yorker shit” (as Charlie Kaufman called it in Adaptation) and Esquire writers don’t have the luxury of hanging around a subject’s milieu for three months soaking up color and detail like Gay Talese did when Frank Sinatra had a cold back in 1966.

“You’ve got a top-down world where these magazines, in most cases, are controlled by large corporations,” says Mr. Samuels. “They have a business model for a magazine that’s gonna work. The power has shifted to editors. Why? Because an editor-driven magazine can put out the same product every month. That’s appealing in the short run in terms of being able to assure advertisers.”

At the lower end of this top-down equation, “writers are providing a sophisticated kind of ad copy that’s supposed to fill a certain hole.”

In the introduction to Only Love, Mr. Samuels calls his two books his “final good-bye to the dying industry that has paid my bills in a sporadic if generally well-meaning fashion for the past decade.”

Today, he calls that “the lamest farewell that anyone’s ever made,” closer in spirit to Jay-Z’s short-lived retirement from rap than a true end to his writing career. The current Atlantic features his cover story about the paparazzi that swarm Britney Spears, and he has two pieces coming out in The New Yorker in the near future.

“He’s a victim of his own success,” Jack Shafer said. “You see it happen at magazines, you see it more at newspapers. Someone hits their 40’s and they say, ‘Well, I’ve been in The New Yorker, what do I do next?’ What they have a hard time swallowing is more of the same.” Comparing Samuels to Tom Wolfe, Shafer thinks the writer needs to find his own Merry Band of Pranksters to inspire a book-length nonfiction yarn like The Electric Kool-Aid Acid Test. “I just hope he doesn’t become a novelist.”

Sorry, Jack. Mr. Samuels is working on a novel—his second, since his first, “a fractured, disembodied mess,” will never see the light of day. “It sucked for a lot of reasons. I smoked a helluva lot of pot when I wrote it. … But there’s some really good stuff in it that I’m intending to steal.”

He’ll continue writing for magazines, too, since it’s all he’s ever known. “I really didn’t have any choice. There was really nothing else I could do.”