In “Generation X,” the 1991 novel that defined the generation born in the 1960s and 1970s, Douglas Coupland chronicled a group of young adults who learn to reconcile themselves to “diminishing expectations of material wealth.” Lessness, Mr. Coupland called this philosophy.

For many of the Gen X-ers who embarked on creative careers in the years after the novel was published, lessness has come to define their professional lives.

If you entered media or image-making in the ’90s — magazine publishing, newspaper journalism, photography, graphic design, advertising, music, film, TV — there’s a good chance that you are now doing something else for work. That’s because those industries have shrunk or transformed themselves radically, shutting out those whose skills were once in high demand.

“I am having conversations every day with people whose careers are sort of over,” said Chris Wilcha, a 53-year-old film and TV director in Los Angeles.

Talk with people in their late 40s and 50s who once imagined they would be able to achieve great heights — or at least a solid career while flexing their creative muscles — and you are likely to hear about the photographer whose work dried up, the designer who can’t get hired or the magazine journalist who isn’t doing much of anything.

Gen X-ers grew up as the younger siblings of the baby boomers, but the media landscape of their early adult years closely resembled that of the 1950s: a tactile analog environment of landline telephones, tube TV sets, vinyl records, glossy magazines and newspapers that left ink on your hands.

When digital technology began seeping into their lives, with its AOL email accounts, Myspace pages and Napster downloads, it didn’t seem like a threat. But by the time they entered the primes of their careers, much of their expertise had become all but obsolete.

More than a dozen members of Generation X interviewed for this article said they now find themselves shut out, economically and culturally, from their chosen fields.

“My peers, friends and I continue to navigate the unforeseen obsolescence of the career paths we chose in our early 20s,” Mr. Wilcha said. “The skills you cultivated, the craft you honed — it’s just gone. It’s startling.”

Every generation has its burdens. The particular plight of Gen X is to have grown up in one world only to hit middle age in a strange new land. It’s as if they were making candlesticks when electricity came in. The market value of their skills plummeted.

Karen McKinley, 55, an advertising executive in Minneapolis, has seen talented colleagues “thrown away,” she said, as agencies have merged, trimmed staff and focused on fast, cheap social media content over elaborate photo shoots.

“Twenty years ago, you would actually have a shoot,” Ms. McKinley said. “Now, you may use influencers who have no advertising background.”

In the wake of the influencers comes another threat, artificial intelligence, which seems likely to replace many of the remaining Gen X copywriters, photographers and designers. By 2030, ad agencies in the United States will lose 32,000 jobs, or 7.5 percent of the industry’s work force, to the technology, according to the research firm Forrester.

Last September, Ms. McKinley co-founded Geezer Creative, an ad agency intended to be a haven for Gen X talent. “We’ve been absolutely bombarded by creative folks over 50 — or even approaching 50 — because they’re terrified,” she said.

The shedding of jobs and upending of longstanding business models have come at a bad time for Gen X-ers. The cost of living has skyrocketed, especially in coastal cities, and the burdens of mortgages, children’s college tuitions and elder care can be heaviest in middle age. Retirement isn’t that far off, theoretically — but Gen X-ers are less secure financially than baby boomers and lack sufficient retirement savings, according to recent surveys.

The old economy still holds sway in a few places — legacy media companies that didn’t get devoured by the internet, film studios that remain flush with cash. But even at those businesses the number of jobs has gone down, and the workers are uneasy. What’s to prevent their little island from going under with the next wave of change?

‘Death Throes’

Steve Kandell couldn’t believe his luck. Growing up as a fan of punk and alternative rock in suburban New Jersey in the 1980s, he had been an avid reader of music magazines — and now here he was, working for Spin, the Gen-X successor to Rolling Stone.

He assigned and edited features. He wrote cover stories about Bruce Springsteen, Amy Winehouse and U2. Spin paid for his reporting trips and gave him weeks to write his articles, which could run as long as 5,000 words.

In keeping with the generational stereotype, Mr. Kandell had been a slacker in his 20s. He landed his first big job in New York in 2002, when he was 30. It was the early days of the internet, but print publications were still thick with ads.

So he was happy to sign on as an assistant editor at Maxim, a magazine that was part of the short-lived “laddie” trend. At its height, it had a paid monthly circulation of more than 2.5 million, far surpassing the readerships of GQ and Esquire, which began to look staid by comparison.

“I was in my 30s, making $31,000 a year,” Mr. Kandell said. “I remember an editor said, ‘You don’t want to work here? There will be a line around the block.’ There was this sense that you get to do this.”

By the time he joined Spin in 2007, the industry was in trouble. As readers spent more time online, magazines reliant on print ads were flailing. In the early 2000s, Spin’s monthly circulation was 530,000; by 2011, it was 460,000 and falling fast.

Like many other publications, Spin tried to remake itself as an online brand. It started an iPad version and beefed up its website to compete with a digital rival, Pitchfork. In 2012, the print edition went bimonthly, and Spin started charging less for ads. Then it was sold to Buzzmedia, an owner of music and celebrity websites. The print edition folded.

“We were in the death throes,” Mr. Kandell said, “whether we knew it or not.”

The changes affected other fields, too. When photography went digital, photo lab technicians and manual retouchers were suddenly as inessential as medieval scribes. The ubiquity of smartphone cameras and easy-to-use editing software made those in possession of the old skills seem almost quaint.

Chris Gentile, who was the creative director of the in-house photo studio at the magazine company Condé Nast from 2004 to 2011, said that top photographers used to earn five figures for a shoot. “Now,” he said, “you can hire a 20-year-old kid who will do the job for $500.”

Carl Chisolm, a photographer who grew up in Harlem and whose credits include shooting Anna Wintour for a MasterClass campaign, said that editorial budgets were already shrinking by the time he started his career in New York in the mid-2000s. “There’s no way you can survive anymore being strong at one thing,” Mr. Chisolm, 45, said. “I worked at a studio, I photo-assisted, I did production work — all while shooting small jobs for myself.”

Even now, he added, “if things are truly slow, I’m not above assisting friends on their shoots. I have a family.”

In advertising, brands ditched print and TV campaigns that required large crews for marketing plans that relied on social media posts, a trend that started with the debut of Instagram in 2010.

“That TV spot you spent six months on now becomes a TikTok execution you spend six days on,” said Greg Paull, principal of R3, a marketing consultancy.

Pam Morris, 54, a freelance prop stylist, noticed another unsettling trend a few years ago, when a U.S. client asked her to art-direct a crew in Asia remotely for a shoot. “They’re just outsourcing,” she said. “It must be cheaper.”

Ms. Morris added that, in her group chats with colleagues, the main topic lately has been the effect of A.I. and computer generated imagery on ad campaigns. “If an art director can say, ‘Give me an image of X, Y, Z,’ what does that mean for our jobs, if they don’t need to have actual photo shoots anymore?” she said.

Similar shifts have taken place in music, television and film. Software like Pro Tools has reduced the need for audio engineers and dedicated recording studios; A.I., some fear, may soon take the place of actual musicians. Streaming platforms typically order fewer episodes per season than the networks did in the heyday of “Friends” and “ER.” Big studios have slashed budgets, making life for production crews more financially precarious.

Typically, workers in their 40s and 50s are entering their peak earning years. But for many Gen-X creatives, compensation has remained flat or decreased, factoring in the rising cost of living. The usual rate for freelance journalists is 50 cents to $1 per word — the same as it was 25 years ago.

The precariousness has affected even those who have risen to corporate posts in the media industry. For nearly 20 years, Liza Demby managed writers in the marketing department at Nickelodeon, the children’s cable network. She started there in 2005, the year YouTube went live.

When viewers started dropping cable subscriptions, revenues declined. Ms. Demby learned to embrace new technology while surviving “around eight billion rounds of layoffs,” she said.

“My job never stayed the same,” she added, “because the industry was transforming under our feet.”

Last August, Nickelodeon’s corporate parent, Paramount, cut $500 million in costs and eliminated thousands of employees. In her 40s, Ms. Demby was out of a job.

Divorced and living in a rented apartment in Brooklyn with her two school-age children, she is drawing from her severance package while considering her next career move. Working freelance, she has come up with marketing ideas and creative content for family-oriented media brands.

“It’s exhilarating, but there’s an undercurrent of terror,” Ms. Demby said. “My severance goes until July.”

‘Very Scary’

It seems fitting that Gen X-ers would reach middle age amid an upheaval. They always had cursed timing.

Their moment on the cultural center stage was brief — roughly between the release of Nirvana’s “Nevermind” in 1991 and the rise of Britney Spears at decade’s end. Many Gen X icons died young and tragically, a list that includes Kurt Cobain, the Notorious B.I.G., Aaliyah, Philip Seymour Hoffman, Anna Nicole Smith, Tupac Shakur, Brittany Murphy, David Foster Wallace, Shannen Doherty, Elliott Smith, Adam Yauch and Elizabeth Wurtzel.

“As a Gen X-er, you more or less expected to get reamed,” the author Jeff Gordinier wrote in the cultural history “X Saves the World.”

Ms. Morris, the prop stylist, didn’t work for six months during the Covid-19 pandemic. “It was very scary,” she said. She and her husband, who have a teenage daughter together, sold their Brooklyn apartment and moved into a rental.

The profit from the sale allowed them to pay off debt and put some savings aside. But then Ms. Morris’s husband, a 59-year-old creative director and artist, was laid off, turning them both into gig workers.

Ms. Morris recently took a course to become a postpartum doula. “I’ve been making images to sell things to people for many, many years now,” she said. “I’m looking for the next act.”

Aside from lost income, there is the emotional toll — feelings of grief and loss — experienced by those whose careers are short-circuited. Some may say that the Gen X-ers in publishing, music, advertising and entertainment were lucky to have such jobs at all, that they stayed too long at the party. But it’s hard to leave a vocation that provided fulfillment and a sense of identity. And it isn’t easy to reinvent yourself in your 50s, especially in industries that put a premium on youth culture.

“I know people who said, ‘Screw this, I’m going to become a postal worker,’” said Ms. McKinley, the ad industry veteran. “There are still a lot of people who are freelancing, but it’s dried up quite a bit in recent years. It’s painful.”

‘What Now?’

As opportunities and incomes dwindle, Gen X-ers in creative fields are weighing their options. Move to a lower-cost place and remain committed to the work you love? Look for a bland corporate job that might provide health insurance and a steady paycheck until retirement?

One of the many Gen X-ers asking these questions is Mr. Wilcha, the TV and movie director. In the mid-2000s, he made a devil’s bargain for someone who grew up on punk rock: He started shooting commercials for Chevrolet, Facebook and Apple, among other companies, to support his family and fund his passion, documentary films.

He had a cult hit with his debut, “The Target Shoots First.” It was a deadpan chronicle comprising footage he had shot during his first job out of college, at Columbia Records; HBO broadcast it in 2001. But cult hits don’t pay the bills. When he shifted his focus to making TV commercials, his documentary projects remained unfinished.

Then came a plot twist. Those commercial jobs grew scarce because of the consolidation of ad agencies and the rise of marketing content plucked from social media. And with Hollywood banking on superhero movies, Mr. Wilcha faced new competition from acclaimed directors who had once specialized in the kind of mid-budget films that the studios had practically stopped making.

“Now it’s a knife fight for every job,” he said. “The cruel irony is, the thing I perceived as the sellout move is in free-fall.”

He decided to recommit to his first love. The result, the documentary “Flipside,” released last year, is a personal film about the trade-offs required to support yourself as an artist. In it, he weaves together footage from his unfinished projects while grappling with his career choices in a wry voice-over narrative.

For the theatrical release, he worked with Oscilloscope, an independent distributor founded by Mr. Yauch of the Beastie Boys, and he often presented the film himself.

“It felt very ’90s,” he said. “It was that indie rock model: Get in the van, tour with the thing, get bodies in the seats. It made no money. But what it did do — and this is what I believe as a Gen X creative person — it confirmed my belief that continuing to make stuff is the path forward.”

Mr. Gentile, the former photo studio manager at Condé Nast, went through something similar. The company was cutting costs as the consultancy McKinsey & Company roamed the halls, and he came face to face with his own irrelevance. He was 40, with an artistic background.

“Who would hire me?” he thought. “Maybe this is where I jump off.”

As a sideline, Mr. Gentile, an avid surfer, had opened a surf shop, Pilgrim, in Williamsburg, Brooklyn. He quit his day job and dedicated himself to the store. He and his wife, Erin Norfleet Gentile, have since expanded it into a clothing brand.

“One thing I’m grateful for, and it’s a strength of my generation, is we weren’t promised anything,” Mr. Gentile said. “I was prepared to struggle.”

Mr. Kandell, the former magazine editor, also had a reckoning.

After Spin stopped appearing on newsstands, he took a job at BuzzFeed, the news and entertainment site that was seen as the future of media at the time. By 2017 BuzzFeed was just another struggling outlet that was doing mass layoffs. Mr. Kandell, then in his mid-40s, married with a child, left for another media outlet. His wife also worked in media.

“Then we had a second kid, and we lived in a small New York apartment,” he said. “And it felt like the only thing we and our friends talked about was, ‘Well, what now’?”

He and his family moved to California, where he took an editorial position at a tech company. The job gave him some security and allowed him to contemplate a second career.

He went back to school and earned a master’s degree in clinical psychology. For the past three years, Mr. Kandell has continued at the tech company while practicing as a therapist on nights and weekends to earn his state license.

He’s still adjusting, though, after having had a career as a Gen X rock guy. “It’s not the same as working at a scrappy music magazine, where you have all the back issues in an attic somewhere,” he said. And yet, he added, he likes having a job that is separate from his old identity. And the mental health sector seems likely to survive the next disruption — and perhaps even benefit from it.

At a party recently, someone asked Mr. Kandell what he did for a living. He took a breath and for the first time he answered, “I’m a therapist.”